subject:(Dipolar cycloaddition)

University of Montana

1. Weaver, Matthew Jacob. IMPROVED SYNTHESIS OF 3-ARYL-ISOXAZOLES AS INTERMEDIATES FOR NOVEL G-QUADRUPLEX BINDING ANTI-TUMOR AGENTS.

Degree: MS, 2013, University of Montana

URL: https://scholarworks.umt.edu/etd/558

► As a promising new target for chemotherapy G-quadruplexes (G4) have drawn great interest from the scientific community. Current chemotherapeutic agents exhibit broad toxicity to patients;… (more)

Subjects/Keywords: 1; 3-dipolar cycloaddition; g4; isoxazole; quadruplex

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APA (6^th Edition):

Weaver, M. J. (2013). IMPROVED SYNTHESIS OF 3-ARYL-ISOXAZOLES AS INTERMEDIATES FOR NOVEL G-QUADRUPLEX BINDING ANTI-TUMOR AGENTS. (Masters Thesis). University of Montana. Retrieved from https://scholarworks.umt.edu/etd/558

Chicago Manual of Style (16^th Edition):

Weaver, Matthew Jacob. “IMPROVED SYNTHESIS OF 3-ARYL-ISOXAZOLES AS INTERMEDIATES FOR NOVEL G-QUADRUPLEX BINDING ANTI-TUMOR AGENTS.” 2013. Masters Thesis, University of Montana. Accessed April 15, 2021. https://scholarworks.umt.edu/etd/558.

MLA Handbook (7^th Edition):

Weaver, Matthew Jacob. “IMPROVED SYNTHESIS OF 3-ARYL-ISOXAZOLES AS INTERMEDIATES FOR NOVEL G-QUADRUPLEX BINDING ANTI-TUMOR AGENTS.” 2013. Web. 15 Apr 2021.

Vancouver:

Weaver MJ. IMPROVED SYNTHESIS OF 3-ARYL-ISOXAZOLES AS INTERMEDIATES FOR NOVEL G-QUADRUPLEX BINDING ANTI-TUMOR AGENTS. [Internet] [Masters thesis]. University of Montana; 2013. [cited 2021 Apr 15]. Available from: https://scholarworks.umt.edu/etd/558.

Council of Science Editors:

Weaver MJ. IMPROVED SYNTHESIS OF 3-ARYL-ISOXAZOLES AS INTERMEDIATES FOR NOVEL G-QUADRUPLEX BINDING ANTI-TUMOR AGENTS. [Masters Thesis]. University of Montana; 2013. Available from: https://scholarworks.umt.edu/etd/558

Universidad de Extremadura

2. García de la Concepción, Juan. Estudio teórico-experimental de la reactividad 1,3-dipolar de tioisomünchnonas bicíclicas .

Degree: 2019, Universidad de Extremadura

URL: http://hdl.handle.net/10662/8634

► La reacción de cicloadición 1,3-dipolar se introdujo en 1960 como un método general de síntesis de anillos de cinco miembros y, en la actualidad, constituye… (more)

Subjects/Keywords: Cicloadición 1,3-dipolar; Heterociclos mesoiónicos; Química computacional; 1,3-Dipolar cycloaddition; Mesoionic heterocycles; Computational chemistry

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APA · Chicago · MLA · Vancouver · CSE | Export to Zotero / EndNote / Reference Manager

APA (6^th Edition):

García de la Concepción, J. (2019). Estudio teórico-experimental de la reactividad 1,3-dipolar de tioisomünchnonas bicíclicas . (Thesis). Universidad de Extremadura. Retrieved from http://hdl.handle.net/10662/8634

Note: this citation may be lacking information needed for this citation format:
Not specified: Masters Thesis or Doctoral Dissertation

Chicago Manual of Style (16^th Edition):

García de la Concepción, Juan. “Estudio teórico-experimental de la reactividad 1,3-dipolar de tioisomünchnonas bicíclicas .” 2019. Thesis, Universidad de Extremadura. Accessed April 15, 2021. http://hdl.handle.net/10662/8634.

Note: this citation may be lacking information needed for this citation format:
Not specified: Masters Thesis or Doctoral Dissertation

MLA Handbook (7^th Edition):

García de la Concepción, Juan. “Estudio teórico-experimental de la reactividad 1,3-dipolar de tioisomünchnonas bicíclicas .” 2019. Web. 15 Apr 2021.

Vancouver:

García de la Concepción J. Estudio teórico-experimental de la reactividad 1,3-dipolar de tioisomünchnonas bicíclicas . [Internet] [Thesis]. Universidad de Extremadura; 2019. [cited 2021 Apr 15]. Available from: http://hdl.handle.net/10662/8634.

Note: this citation may be lacking information needed for this citation format:
Not specified: Masters Thesis or Doctoral Dissertation

Council of Science Editors:

García de la Concepción J. Estudio teórico-experimental de la reactividad 1,3-dipolar de tioisomünchnonas bicíclicas . [Thesis]. Universidad de Extremadura; 2019. Available from: http://hdl.handle.net/10662/8634

Note: this citation may be lacking information needed for this citation format:
Not specified: Masters Thesis or Doctoral Dissertation

McMaster University

3. Rambarran, Talena. New Routes to Functional Siloxanes: Applications of the Thermal Azide-Alkyne Cycloaddition for the Silicone Chemist.

Degree: PhD, 2016, McMaster University

URL: http://hdl.handle.net/11375/20557

►

Silicone oils (polysiloxane) and elastomers are a class of hydrophobic polymers with an extensive range of uses. While the high hydrophobicity can be beneficial in… (more)

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Silicone oils (polysiloxane) and elastomers are a class of hydrophobic polymers with an extensive range of uses. While the high hydrophobicity can be beneficial in a variety of applications, it is not universally the case. Modification strategies for both fluid and elastomeric polydimethylsiloxane (PDMS) must be employed to create silicones with the appropriate properties for a given application, including enhanced hydrophilicity. Derivatization of PDMS leads to functional silicones with unique properties and added value. Strategies have been developed to modify both fluid and elastomeric PDMS, however, they all have varying degrees of drawbacks: the use of sophisticated equipment or expensive catalysts, restrictions to certain types of solvents, cumbersome multi-step synthetic procedures and surface reversion are some of the challenges faced. There is an opportunity to develop a simple and generic method for the controlled functionalization of PDMS. The Sharpless concept of ‘Click’ chemistry was an ideal approach to solving some of these challenges. Following nature’s lead, these reactions that are modular, wide in scope, high yielding, have simple reaction conditions and generate inoffensive byproducts. Herein, a synthetic method to functionalize silicones using the thermal Huisgen 1,3-dipolar cycloaddition of azides to alkynes is described. Initial exploration focused on the creation of inherently reactive elastomers that could be modified with a model hydrophilic moiety, poly(ethylene glycol). This was extended to the creation of amphiphilic multi-functional polysiloxanes and amphiphilic networks. Furthermore, the ‘Click’ approach was used to solve challenges faced in applications where silicones find use. The method described overcomes silicone modification challenges. The cycloaddition reaction is tolerant to many reaction conditions, is orthoganol to a variety of chemical reactions, does not require the use of a catalyst, the starting functional groups and bonds formed are stable and the reaction is high yielding, positioning the Huisgen ‘click’ reaction is an exceptional synthetic tool for the silicone chemist.

Dissertation

Doctor of Philosophy (PhD)

Polydimethylsiloxane (PDMS or silicone) fluids and elastomers are materials that find use in many applications owing to the many desirable properties they possess; personal care products, electrical insulators, sealants and biomedical are examples of products containing silicone. Native PDMS is highly hydrophobic (water repellent) and certain applications require silicones that are more compatible in environments containing water. Methods have been developed to modify both fluid and elastomeric silicones; incorporation of different molecules or polymers can enhance the properties of silicone for various applications or create unique materials. However, many of these methods have certain drawbacks: the use of sophisticated equipment, expensive ingredients, or a lack of permanence. For this reason, a new method to modify fluid and elastomeric silicones…

Advisors/Committee Members: Brook, Michael A., Chemistry.

Subjects/Keywords: silicones; azide-alkyne cycloaddition; click chemistry; modification; Huisgen 1,3 dipolar cycloaddition; thermal; PDMS

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APA · Chicago · MLA · Vancouver · CSE | Export to Zotero / EndNote / Reference Manager

APA (6^th Edition):

Rambarran, T. (2016). New Routes to Functional Siloxanes: Applications of the Thermal Azide-Alkyne Cycloaddition for the Silicone Chemist. (Doctoral Dissertation). McMaster University. Retrieved from http://hdl.handle.net/11375/20557

Chicago Manual of Style (16^th Edition):

Rambarran, Talena. “New Routes to Functional Siloxanes: Applications of the Thermal Azide-Alkyne Cycloaddition for the Silicone Chemist.” 2016. Doctoral Dissertation, McMaster University. Accessed April 15, 2021. http://hdl.handle.net/11375/20557.

MLA Handbook (7^th Edition):

Rambarran, Talena. “New Routes to Functional Siloxanes: Applications of the Thermal Azide-Alkyne Cycloaddition for the Silicone Chemist.” 2016. Web. 15 Apr 2021.

Vancouver:

Rambarran T. New Routes to Functional Siloxanes: Applications of the Thermal Azide-Alkyne Cycloaddition for the Silicone Chemist. [Internet] [Doctoral dissertation]. McMaster University; 2016. [cited 2021 Apr 15]. Available from: http://hdl.handle.net/11375/20557.

Council of Science Editors:

Rambarran T. New Routes to Functional Siloxanes: Applications of the Thermal Azide-Alkyne Cycloaddition for the Silicone Chemist. [Doctoral Dissertation]. McMaster University; 2016. Available from: http://hdl.handle.net/11375/20557

4. Rouzier, Florian. Synthèse de nouveaux analogues C-glycosidiques d'alpha-galactosylcéramides : couplage des glycolipides à des anticorps spécifiques : Synthesis of new C-glycosidic analogs of alpha-galactosylceramides : glycoconjugates synthesis combining glycolipid and targeting agent.

Degree: Docteur es, Chimie moléculaire et macromoléculaire, 2018, Le Mans

URL: http://www.theses.fr/2018LEMA1027

►

Le sujet de thèse concerne l’immunothérapie induite par des glycolipides synthétiques dont le chef de file est le KRN7000. Ce composé montre une activité à… (more)

▼

Le sujet de thèse concerne l’immunothérapie induite par des glycolipides synthétiques dont le chef de file est le KRN7000. Ce composé montre une activité à stimuler le système immunitaire renforçant l’action antitumorale. Cependant, comme la plupart des principes actifs, le KRN 7000 n’est pas spécifique des cellules tumorales. Pour pallier ce manque de spécificité, nous avons envisagé de coupler des glycolipides à un agent ciblant des cellules tumorales selon deux approches. La première a consisté à lier de manière covalente l’agent ciblant au glycolipide via un espaceur, ce qui a permis d’évaluer si le greffage de cet immunostimulant sur l’agent ciblant ne perturberait pas la reconnaissance par le récepteur membranaire. Concernant la seconde approche, une étude préliminaire reposant sur le relargage du KRN7000 a été abordé en préparant une prodrogue du glycolipide. Un autre problème du KRN7000 est qu’il n’est pas sélectif vis-à-vis de deux voies d’activation du système immunitaire. Pour pallier ce problème, la synthèse de nouveaux analogues C-glycosidiques d’alpha-galactosylcéramides plus stables et plus sélectifs de la voie Th1 a été envisagée. La stratégie de synthèse met en œuvre une cycloaddition 1,3-dipolaire entre un C-vinyl glycoside et une nitrone. Dans un premier temps, une étude méthodologique de cette réaction a d’abord été réalisée. Dans un deuxième temps, la fonctionnalisation du cycle isoxazolidine puis son ouverture devrait permettre d’accéder aux analogues ciblés.

This PhD work concerns glycolipid-induced activation of immune system with KRN7000 as lead compound. This latter has shown its ability to stimulate NKT cells which are T cells of the immune system resulting in potent antitumor activity. However, like lots of drugs, KRN7000 is not specific for tumor cells. To tackle this lack of specificity, we plan to graft glycolipids to a targeting agent for tumor cells following two approaches. The aim of the first one was to bind covalently the glycolipid to the targeting agent in order to determine the effect of the glycolipid grafting onto the targeting agent on the recognition by the membrane receptor. Regarding the second approach, a preliminary study based on the KRN7000 release was performed by synthesizing a glycolipid prodrug. Another drawback of the KRN7000 is the lack of selectivity towards two ways of activation of the immune system. In order to favor the Th1 immune response, the synthesis of new C-glycosidic analogues of alpha-galactosylceramides was implemented. The synthetic strategy has involved a 1,3-dipolar cycloaddition between a C-vinyl glycoside and a nitrone. First, a methodologic study about this reaction was performed. Then functionalization of the obtained isoxazolidine ring and the N-O bond cleavage should lead to the expected original analogs.

Advisors/Committee Members: Guillarme, Stéphane (thesis director), Pipelier, Muriel (thesis director).

Subjects/Keywords: Galactosylcéramides; Vectorisation; C-glycoside; Cycloaddition 1,3-dipolaire; Galactosylceramides; Vectorization; C-glycoside; 1,3-dipolar cycloaddition; 547

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APA · Chicago · MLA · Vancouver · CSE | Export to Zotero / EndNote / Reference Manager

APA (6^th Edition):

Rouzier, F. (2018). Synthèse de nouveaux analogues C-glycosidiques d'alpha-galactosylcéramides : couplage des glycolipides à des anticorps spécifiques : Synthesis of new C-glycosidic analogs of alpha-galactosylceramides : glycoconjugates synthesis combining glycolipid and targeting agent. (Doctoral Dissertation). Le Mans. Retrieved from http://www.theses.fr/2018LEMA1027

Chicago Manual of Style (16^th Edition):

Rouzier, Florian. “Synthèse de nouveaux analogues C-glycosidiques d'alpha-galactosylcéramides : couplage des glycolipides à des anticorps spécifiques : Synthesis of new C-glycosidic analogs of alpha-galactosylceramides : glycoconjugates synthesis combining glycolipid and targeting agent.” 2018. Doctoral Dissertation, Le Mans. Accessed April 15, 2021. http://www.theses.fr/2018LEMA1027.

MLA Handbook (7^th Edition):

Rouzier, Florian. “Synthèse de nouveaux analogues C-glycosidiques d'alpha-galactosylcéramides : couplage des glycolipides à des anticorps spécifiques : Synthesis of new C-glycosidic analogs of alpha-galactosylceramides : glycoconjugates synthesis combining glycolipid and targeting agent.” 2018. Web. 15 Apr 2021.

Vancouver:

Rouzier F. Synthèse de nouveaux analogues C-glycosidiques d'alpha-galactosylcéramides : couplage des glycolipides à des anticorps spécifiques : Synthesis of new C-glycosidic analogs of alpha-galactosylceramides : glycoconjugates synthesis combining glycolipid and targeting agent. [Internet] [Doctoral dissertation]. Le Mans; 2018. [cited 2021 Apr 15]. Available from: http://www.theses.fr/2018LEMA1027.

Council of Science Editors:

Rouzier F. Synthèse de nouveaux analogues C-glycosidiques d'alpha-galactosylcéramides : couplage des glycolipides à des anticorps spécifiques : Synthesis of new C-glycosidic analogs of alpha-galactosylceramides : glycoconjugates synthesis combining glycolipid and targeting agent. [Doctoral Dissertation]. Le Mans; 2018. Available from: http://www.theses.fr/2018LEMA1027

5. Sandhya, R. Studies On Developing A Facile Route For The Synthesis Of Highly Substituted Quinoline And Indole Derivatives.

Degree: Applied Chemistry, 2013, Cochin University of Science and Technology

URL: http://dyuthi.cusat.ac.in/purl/3745

►

the thesis entitled “STUDIES ON DEVELOPING A FACILE ROUTE FOR THE SYNTHESIS OF HIGHLY SUBSTITUTED QUINOLINE AND INDOLE DERIVATIVES” portrays our attempt to revisit the… (more)

Subjects/Keywords: 1,3-Dipolar Cycloaddition; Nitrones; Synthesis of Nitrones; N-arylnitrones

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APA (6^th Edition):

Sandhya, R. (2013). Studies On Developing A Facile Route For The Synthesis Of Highly Substituted Quinoline And Indole Derivatives. (Thesis). Cochin University of Science and Technology. Retrieved from http://dyuthi.cusat.ac.in/purl/3745

Note: this citation may be lacking information needed for this citation format:
Not specified: Masters Thesis or Doctoral Dissertation

Chicago Manual of Style (16^th Edition):

Sandhya, R. “Studies On Developing A Facile Route For The Synthesis Of Highly Substituted Quinoline And Indole Derivatives.” 2013. Thesis, Cochin University of Science and Technology. Accessed April 15, 2021. http://dyuthi.cusat.ac.in/purl/3745.

Note: this citation may be lacking information needed for this citation format:
Not specified: Masters Thesis or Doctoral Dissertation

MLA Handbook (7^th Edition):

Sandhya, R. “Studies On Developing A Facile Route For The Synthesis Of Highly Substituted Quinoline And Indole Derivatives.” 2013. Web. 15 Apr 2021.

Vancouver:

Sandhya R. Studies On Developing A Facile Route For The Synthesis Of Highly Substituted Quinoline And Indole Derivatives. [Internet] [Thesis]. Cochin University of Science and Technology; 2013. [cited 2021 Apr 15]. Available from: http://dyuthi.cusat.ac.in/purl/3745.

Note: this citation may be lacking information needed for this citation format:
Not specified: Masters Thesis or Doctoral Dissertation

Council of Science Editors:

Sandhya R. Studies On Developing A Facile Route For The Synthesis Of Highly Substituted Quinoline And Indole Derivatives. [Thesis]. Cochin University of Science and Technology; 2013. Available from: http://dyuthi.cusat.ac.in/purl/3745

Note: this citation may be lacking information needed for this citation format:
Not specified: Masters Thesis or Doctoral Dissertation

University of Michigan

6. Ferguson, Kyle. A New Decarboxylase: A Mechanistic Characterization of PrFMN Decarboxylase FDC1.

Degree: PhD, Chemistry, 2018, University of Michigan

URL: http://hdl.handle.net/2027.42/144153

► The large number of inexpensive carboxylic acids found in nature has spurred research to convert carboxylic acids to an assortment of other functional groups for… (more)

▼ The large number of inexpensive carboxylic acids found in nature has spurred research to convert carboxylic acids to an assortment of other functional groups for a range of purposes. To accomplish this, researchers employ a variety of strategies ranging from heat and heavy metals to biocatalysts. Ferulic acid decarboxylase (FDC1) from Saccharomyces cerevisiae is a member of the UbiD family of decarboxylase enzymes. The UbiD family of proteins consists of prenylated flavin (PrFMN)-dependent enzymes that catalyze the reversible decarboxylation of a wide variety of aromatic carboxylic acids. The UbiD family attracted interest as a biocatalyst to produce chemical feedstocks from renewable sources and as a potential target for antimicrobial research. The UbiD enzyme, FDC1, and its associated protein partner, PAD1, were identified as being responsible for the detoxification of aromatic carboxylic acids in fungi. How PAD1/FDC1 work together to facilitate the decarboxylation of toxic aromatic acids remains an open question. The genes encoding PAD1 and FDC1 were independently expressed in E. coli with the PAD1 homolog UbiX knocked out. Independently, FDC1 and PAD1 were unable to decarboxylate phenylacrylic acids. Moreover, PAD1 failed to decarboxylate any of the phenylacrylic acids by itself. In contrast FDC1 was able to recover its decarboxylase activity upon the addition of PAD1 or its homolog UbiX, indicating FDC1 was solely responsible for the decarboxylase activity. Co-expression of FDC1 and PAD1 coupled with the sole purification of FDC1 exhibited spectral characteristics of a reduced flavin in an aerobic system. This increased the kcat by 8-fold. The holo-FDC1 crystal structure (PDB 4ZAC) provided insight into the decarboxylation mechanism of FDC1. FDC1 was proposed to perform a unique and controversial 1,3-dipolar cycloaddition mechanism. To address the controversial nature of the proposed mechanism KIE and a Hammett analysis were utilized to ascertain whether FDC1 undergoes the proposed mechanism or a completely different mechanism. The solvent isotope effects, normal secondary isotope effects, and the negative slope of the Hammett analysis are consist with the rate-determining step being the breakdown of the PrFMN-product adduct through a non-concerted cyclo-elimination reaction, and provides evidence in favor of the novel 1,3-dipolar cycloaddition mechanism. The proposed mechanism involves the formation of a novel pentacyclic intermediate through a novel 1,3-dipolar cycloaddition mechanism between PrFMN and the β -γ double bond of the substrate, which serves to activate the substrate towards decarboxylation. In order to trap this hypothesized intermediate, a mechanism-based inhibitor 2-fluoro-2-nitro-vinylbenzene (FNVB) was used to trap the putative cyclo-addition intermediate. Upon incubating FNVB with FDC1, there was a red-shift in the flavin spectrum which is reminiscent of an uncharged N5, C4α dialkyl flavin adduct and is consistent with a 1,3-dipolar cycloadduct. Finally by pushing the… Advisors/Committee Members: Marsh, E Neil G (committee member), Palfey, Bruce Allan (committee member), Koutmou, Kristin (committee member), Walter, Nils G (committee member).

Subjects/Keywords: FDC1 Decarboxylase; PrFMN; Enzymatic 1,3 Dipolar Cycloaddition; Chemistry; Science

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APA · Chicago · MLA · Vancouver · CSE | Export to Zotero / EndNote / Reference Manager

APA (6^th Edition):

Ferguson, K. (2018). A New Decarboxylase: A Mechanistic Characterization of PrFMN Decarboxylase FDC1. (Doctoral Dissertation). University of Michigan. Retrieved from http://hdl.handle.net/2027.42/144153

Chicago Manual of Style (16^th Edition):

Ferguson, Kyle. “A New Decarboxylase: A Mechanistic Characterization of PrFMN Decarboxylase FDC1.” 2018. Doctoral Dissertation, University of Michigan. Accessed April 15, 2021. http://hdl.handle.net/2027.42/144153.

MLA Handbook (7^th Edition):

Ferguson, Kyle. “A New Decarboxylase: A Mechanistic Characterization of PrFMN Decarboxylase FDC1.” 2018. Web. 15 Apr 2021.

Vancouver:

Ferguson K. A New Decarboxylase: A Mechanistic Characterization of PrFMN Decarboxylase FDC1. [Internet] [Doctoral dissertation]. University of Michigan; 2018. [cited 2021 Apr 15]. Available from: http://hdl.handle.net/2027.42/144153.

Council of Science Editors:

Ferguson K. A New Decarboxylase: A Mechanistic Characterization of PrFMN Decarboxylase FDC1. [Doctoral Dissertation]. University of Michigan; 2018. Available from: http://hdl.handle.net/2027.42/144153

Mahatma Gandhi University

7. Rajesh, C. Novel heterocyclic construction using dipolar cycloaddition reactions of quinonoid compounds.

Degree: 2010, Mahatma Gandhi University

URL: http://shodhganga.inflibnet.ac.in/handle/10603/590

Abbreviation and Bibliography are included Advisors/Committee Members: Nair, G Vijay.

Subjects/Keywords: Quinonoid Compounds; Dipolar Cycloaddition

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APA · Chicago · MLA · Vancouver · CSE | Export to Zotero / EndNote / Reference Manager

APA (6^th Edition):

Rajesh, C. (2010). Novel heterocyclic construction using dipolar cycloaddition reactions of quinonoid compounds. (Thesis). Mahatma Gandhi University. Retrieved from http://shodhganga.inflibnet.ac.in/handle/10603/590

Note: this citation may be lacking information needed for this citation format:
Not specified: Masters Thesis or Doctoral Dissertation

Chicago Manual of Style (16^th Edition):

Rajesh, C. “Novel heterocyclic construction using dipolar cycloaddition reactions of quinonoid compounds.” 2010. Thesis, Mahatma Gandhi University. Accessed April 15, 2021. http://shodhganga.inflibnet.ac.in/handle/10603/590.

Note: this citation may be lacking information needed for this citation format:
Not specified: Masters Thesis or Doctoral Dissertation

MLA Handbook (7^th Edition):

Rajesh, C. “Novel heterocyclic construction using dipolar cycloaddition reactions of quinonoid compounds.” 2010. Web. 15 Apr 2021.

Vancouver:

Rajesh C. Novel heterocyclic construction using dipolar cycloaddition reactions of quinonoid compounds. [Internet] [Thesis]. Mahatma Gandhi University; 2010. [cited 2021 Apr 15]. Available from: http://shodhganga.inflibnet.ac.in/handle/10603/590.

Note: this citation may be lacking information needed for this citation format:
Not specified: Masters Thesis or Doctoral Dissertation

Council of Science Editors:

Rajesh C. Novel heterocyclic construction using dipolar cycloaddition reactions of quinonoid compounds. [Thesis]. Mahatma Gandhi University; 2010. Available from: http://shodhganga.inflibnet.ac.in/handle/10603/590

Note: this citation may be lacking information needed for this citation format:
Not specified: Masters Thesis or Doctoral Dissertation

University of Toronto

8. Youn, Beom. Phosgene-free Synthesis of Verdazyl Radicals and Enantioselective 1,3-dipolar Cycloaddition Reactions of Azomethine Imines Generated in situ from Verdazyl Radicals.

Degree: 2012, University of Toronto

URL: http://hdl.handle.net/1807/35547

►

Verdazyl radicals started receiving attention as substrates for organic synthesis only a few years ago. Since then, the chemistry of verdazyl radicals has advanced at… (more)

Subjects/Keywords: Verdazyl Radical; 1,3-dipolar cycloaddition; enantioselective synthesis; 0490

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APA (6^th Edition):

Youn, B. (2012). Phosgene-free Synthesis of Verdazyl Radicals and Enantioselective 1,3-dipolar Cycloaddition Reactions of Azomethine Imines Generated in situ from Verdazyl Radicals. (Masters Thesis). University of Toronto. Retrieved from http://hdl.handle.net/1807/35547

Chicago Manual of Style (16^th Edition):

Youn, Beom. “Phosgene-free Synthesis of Verdazyl Radicals and Enantioselective 1,3-dipolar Cycloaddition Reactions of Azomethine Imines Generated in situ from Verdazyl Radicals.” 2012. Masters Thesis, University of Toronto. Accessed April 15, 2021. http://hdl.handle.net/1807/35547.

MLA Handbook (7^th Edition):

Youn, Beom. “Phosgene-free Synthesis of Verdazyl Radicals and Enantioselective 1,3-dipolar Cycloaddition Reactions of Azomethine Imines Generated in situ from Verdazyl Radicals.” 2012. Web. 15 Apr 2021.

Vancouver:

Youn B. Phosgene-free Synthesis of Verdazyl Radicals and Enantioselective 1,3-dipolar Cycloaddition Reactions of Azomethine Imines Generated in situ from Verdazyl Radicals. [Internet] [Masters thesis]. University of Toronto; 2012. [cited 2021 Apr 15]. Available from: http://hdl.handle.net/1807/35547.

Council of Science Editors:

Youn B. Phosgene-free Synthesis of Verdazyl Radicals and Enantioselective 1,3-dipolar Cycloaddition Reactions of Azomethine Imines Generated in situ from Verdazyl Radicals. [Masters Thesis]. University of Toronto; 2012. Available from: http://hdl.handle.net/1807/35547

University of Vermont

9. Draghici, Cristian. Discovery of a Novel Ring Fragmentation Reaction; Efficient Preparation of Tethered Aldehyde Ynoates and N-Containing Heterocycles;Radical Addition Approach to Asymmetric Amine Synthesis.

Degree: PhD, Chemistry, 2009, University of Vermont

URL: https://scholarworks.uvm.edu/graddis/70

► This dissertation describes the development of a novel ring fragmentation reaction in which cyclic γ-silyloxy-β-hydroxy-α-diazoesters undergo efficient rupture of the Cβ−Cγ bond when treated with… (more)

Subjects/Keywords: intramolecular dipolar cycloaddition; zaomethine ylides

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APA (6^th Edition):

Draghici, C. (2009). Discovery of a Novel Ring Fragmentation Reaction; Efficient Preparation of Tethered Aldehyde Ynoates and N-Containing Heterocycles;Radical Addition Approach to Asymmetric Amine Synthesis. (Doctoral Dissertation). University of Vermont. Retrieved from https://scholarworks.uvm.edu/graddis/70

Chicago Manual of Style (16^th Edition):

Draghici, Cristian. “Discovery of a Novel Ring Fragmentation Reaction; Efficient Preparation of Tethered Aldehyde Ynoates and N-Containing Heterocycles;Radical Addition Approach to Asymmetric Amine Synthesis.” 2009. Doctoral Dissertation, University of Vermont. Accessed April 15, 2021. https://scholarworks.uvm.edu/graddis/70.

MLA Handbook (7^th Edition):

Draghici, Cristian. “Discovery of a Novel Ring Fragmentation Reaction; Efficient Preparation of Tethered Aldehyde Ynoates and N-Containing Heterocycles;Radical Addition Approach to Asymmetric Amine Synthesis.” 2009. Web. 15 Apr 2021.

Vancouver:

Draghici C. Discovery of a Novel Ring Fragmentation Reaction; Efficient Preparation of Tethered Aldehyde Ynoates and N-Containing Heterocycles;Radical Addition Approach to Asymmetric Amine Synthesis. [Internet] [Doctoral dissertation]. University of Vermont; 2009. [cited 2021 Apr 15]. Available from: https://scholarworks.uvm.edu/graddis/70.

Council of Science Editors:

Draghici C. Discovery of a Novel Ring Fragmentation Reaction; Efficient Preparation of Tethered Aldehyde Ynoates and N-Containing Heterocycles;Radical Addition Approach to Asymmetric Amine Synthesis. [Doctoral Dissertation]. University of Vermont; 2009. Available from: https://scholarworks.uvm.edu/graddis/70

Colorado State University

10. Jiménez-Somarribas, Alberto. Synthetic studies on (-) lemonomycin: construction of the tetracyclic core.

Degree: PhD, Chemistry, 2013, Colorado State University

URL: http://hdl.handle.net/10217/80986

► Documented herein are efforts towards the asymmetric total synthesis of (-)-lemonomycin, a member of the tetrahydroisoquinoline antitumor antibiotics family of natural products. We describe a… (more)

Subjects/Keywords: [3+2] dipolar cycloaddition; Pictet-Spengler reaction; Lemonomycin; asymmetric synthesis

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APA · Chicago · MLA · Vancouver · CSE | Export to Zotero / EndNote / Reference Manager

APA (6^th Edition):

Jiménez-Somarribas, A. (2013). Synthetic studies on (-) lemonomycin: construction of the tetracyclic core. (Doctoral Dissertation). Colorado State University. Retrieved from http://hdl.handle.net/10217/80986

Chicago Manual of Style (16^th Edition):

Jiménez-Somarribas, Alberto. “Synthetic studies on (-) lemonomycin: construction of the tetracyclic core.” 2013. Doctoral Dissertation, Colorado State University. Accessed April 15, 2021. http://hdl.handle.net/10217/80986.

MLA Handbook (7^th Edition):

Jiménez-Somarribas, Alberto. “Synthetic studies on (-) lemonomycin: construction of the tetracyclic core.” 2013. Web. 15 Apr 2021.

Vancouver:

Jiménez-Somarribas A. Synthetic studies on (-) lemonomycin: construction of the tetracyclic core. [Internet] [Doctoral dissertation]. Colorado State University; 2013. [cited 2021 Apr 15]. Available from: http://hdl.handle.net/10217/80986.

Council of Science Editors:

Jiménez-Somarribas A. Synthetic studies on (-) lemonomycin: construction of the tetracyclic core. [Doctoral Dissertation]. Colorado State University; 2013. Available from: http://hdl.handle.net/10217/80986

Colorado State University

11. Smith, Genessa M. Progress toward the total synthesis of citrinadins A and B.

Degree: PhD, Chemistry, 2012, Colorado State University

URL: http://hdl.handle.net/10217/67651

► In 2005 Kobayashi reported the isolation and absolute stereochemistry of Citrinadin A (1) and Citrinadin B (2), novel secondary metabolites of the marine fungus Penicillium… (more)

▼ In 2005 Kobayashi reported the isolation and absolute stereochemistry of Citrinadin A (1) and Citrinadin B (2), novel secondary metabolites of the marine fungus Penicillium citrinum. In addition to their interesting molecular architecture, the citrinadins are biologically active. Both exhibit cytotoxicity against murine leukemia L1210 (IC50 6.2 and 10 μg/mL respectively), and 1 has shown activity against human epidermoid carcinoma KB cells (IC50 6.2 μg/mL). Synthesis of 1 and 2 would allow for further testing of their biological activity and remains the best way to confirm their assigned structures. While, no total synthesis of either natural product has been reported to date, two synthetic approaches toward the citrinadins have been disclosed by Martin and Sorensen. Efforts to synthesize 1 and 2 in the Wood laboratory are based upon a convergent (3+2) dipolar cycloaddition reaction between a spiro-oxindole dipolarophile and a nitrone, where two diastereomeric isoxazolidine cycloadducts are formed. Using the undesired cycloadduct, exploratory studies toward a synthesis of 2 were conducted, resulting in the synthesis of the C3-epi-Citrinadin Core (±)-96. Elaboration of the desired cycloadduct then led to a synthesis of the ent-Citrinadin Core (+)-100. In order gain to access 2, a C7-functionalized spiro-oxindole dipolarophile was employed in the cycloaddition; however, elaboration of the desired C7-functionalized cycloadduct to ent-2 may result in a structural reassignment of 2. Preliminary results suggest that spectral data for the C21-epi-ent diastereomer of 2 (175) match the data reported by Kobayashi for Citrinadin B (2) itself. In an effort to gain access to 1, a (3+2) cycloaddition strategy utilizing a C14-functionalized nitrone was explored. Following the synthesis of three nitrone precursors, a one-pot nitrone formation / (3+2) cycloaddition reaction was developed and one of the cycloadducts was successfully advanced to a key ring-fusion epoxide. Elaboration of this advanced intermediate is expected to eventually provide a total synthesis of Citrinadin A (1). Advisors/Committee Members: Wood, John L. (advisor), Williams, Robert M. (committee member), Ferreira, Eric M. (committee member), Chen, Eugene Y. (committee member), O'Keefe, Garrett J. (committee member).

Subjects/Keywords: (3+2) dipolar cycloaddition; nitrone; Citrinadin B; Citrinadin A

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APA · Chicago · MLA · Vancouver · CSE | Export to Zotero / EndNote / Reference Manager

APA (6^th Edition):

Smith, G. M. (2012). Progress toward the total synthesis of citrinadins A and B. (Doctoral Dissertation). Colorado State University. Retrieved from http://hdl.handle.net/10217/67651

Chicago Manual of Style (16^th Edition):

Smith, Genessa M. “Progress toward the total synthesis of citrinadins A and B.” 2012. Doctoral Dissertation, Colorado State University. Accessed April 15, 2021. http://hdl.handle.net/10217/67651.

MLA Handbook (7^th Edition):

Smith, Genessa M. “Progress toward the total synthesis of citrinadins A and B.” 2012. Web. 15 Apr 2021.

Vancouver:

Smith GM. Progress toward the total synthesis of citrinadins A and B. [Internet] [Doctoral dissertation]. Colorado State University; 2012. [cited 2021 Apr 15]. Available from: http://hdl.handle.net/10217/67651.

Council of Science Editors:

Smith GM. Progress toward the total synthesis of citrinadins A and B. [Doctoral Dissertation]. Colorado State University; 2012. Available from: http://hdl.handle.net/10217/67651

University of Toronto

12. Dang, Jeremy. Verdazyl Radicals as Substrates for the Synthesis of Novel Nitrogen-containing Heterocycles.

Degree: 2010, University of Toronto

URL: http://hdl.handle.net/1807/29984

►

The emergence of verdazyl radicals as starting materials for organic synthesis is providing a unique opportunity to create a variety of distinctive heterocyclic scaffolds. These… (more)

Subjects/Keywords: Verdazyl radicals; 1,3-dipolar cycloaddition; azomethine imine; heterocyclic syntheses; pyrazolotetrazinanone; 0490

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APA (6^th Edition):

Dang, J. (2010). Verdazyl Radicals as Substrates for the Synthesis of Novel Nitrogen-containing Heterocycles. (Masters Thesis). University of Toronto. Retrieved from http://hdl.handle.net/1807/29984

Chicago Manual of Style (16^th Edition):

Dang, Jeremy. “Verdazyl Radicals as Substrates for the Synthesis of Novel Nitrogen-containing Heterocycles.” 2010. Masters Thesis, University of Toronto. Accessed April 15, 2021. http://hdl.handle.net/1807/29984.

MLA Handbook (7^th Edition):

Dang, Jeremy. “Verdazyl Radicals as Substrates for the Synthesis of Novel Nitrogen-containing Heterocycles.” 2010. Web. 15 Apr 2021.

Vancouver:

Dang J. Verdazyl Radicals as Substrates for the Synthesis of Novel Nitrogen-containing Heterocycles. [Internet] [Masters thesis]. University of Toronto; 2010. [cited 2021 Apr 15]. Available from: http://hdl.handle.net/1807/29984.

Council of Science Editors:

Dang J. Verdazyl Radicals as Substrates for the Synthesis of Novel Nitrogen-containing Heterocycles. [Masters Thesis]. University of Toronto; 2010. Available from: http://hdl.handle.net/1807/29984

National University of Ireland – Galway

13. Moynihan, Lorna. Synthesis of Iminosugar C-Glycosides via Tandem Allylic Azide Rearrangement - Huisgen Cycloaddition .

Degree: 2013, National University of Ireland – Galway

URL: http://hdl.handle.net/10379/4253

► Iminosugars are naturally occurring polyhydroxylated alkaloids. These natural mimics of carbohydrates have found clinical use with their biological activity mainly attributed to their inhibition of… (more)

▼ Iminosugars are naturally occurring polyhydroxylated alkaloids. These natural mimics of carbohydrates have found clinical use with their biological activity mainly attributed to their inhibition of glycoprocessing enzymes. The background to this thesis and the intramolecular tandem allylic azide rearrangement – Huisgen cycloaddition are discussed in Chapter 1. Chapter 2 describes the synthesis of iminosugar derivatives from D-glucono-[delta]-lactone which is an extension of work carried out previously in the Murphy group for the preparation of 1-deoxyiminosugars. This route was particularly successful in the highly stereoselective preparation of iminosugars fused to triazoles from an intramolecular rearrangement-cycloaddition between azide and alkyne groups. However the rearrangement-cycloaddition between azide and alkene groups based on intermediates with the glucose configuration suffered from poor yields. An alternative route using a zinc-mediated reductive fragmentation reaction from a variety of commercially available sugars to prepare allylic azide precursors was next explored. This is discussed in Chapters 3-5, which also describe the rearrangement-cycloaddition reactions of these intermediates which lead to iminosugars based on glucose, mannose and galactose. The importance of a conformational constraint to achieve the cycloaddition emerged. Again, the cycloaddition of the glucose intermediates was affected by poor yields. However, results with the mannose and galactose derivatives were more promising. The stereoselectivity was assigned using NMR coupling constants (JH1-H2 and JC1-H1 values), NOEs, X-ray crystallography and comparisons with analytical data for compounds already described in the literature. The stereoselectivities were rationalised with the aid of models built using molecular mechanics. The synthesis of a natural C-glycoside iminosugar was achieved. Overall this thesis demonstrates that an allylic azide rearrangement carried out in tandem with Huisgen cycloaddition is diastereoselective in ring formation and should be useful in organic chemistry. Advisors/Committee Members: Murphy, Paul V (advisor).

Subjects/Keywords: Iminosugar C-Glycosides; 1,3-Dipolar; Cycloaddition; Allylic azide rearrangement; Chemistry

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APA (6^th Edition):

Moynihan, L. (2013). Synthesis of Iminosugar C-Glycosides via Tandem Allylic Azide Rearrangement - Huisgen Cycloaddition . (Thesis). National University of Ireland – Galway. Retrieved from http://hdl.handle.net/10379/4253

Note: this citation may be lacking information needed for this citation format:
Not specified: Masters Thesis or Doctoral Dissertation

Chicago Manual of Style (16^th Edition):

Moynihan, Lorna. “Synthesis of Iminosugar C-Glycosides via Tandem Allylic Azide Rearrangement - Huisgen Cycloaddition .” 2013. Thesis, National University of Ireland – Galway. Accessed April 15, 2021. http://hdl.handle.net/10379/4253.

Note: this citation may be lacking information needed for this citation format:
Not specified: Masters Thesis or Doctoral Dissertation

MLA Handbook (7^th Edition):

Moynihan, Lorna. “Synthesis of Iminosugar C-Glycosides via Tandem Allylic Azide Rearrangement - Huisgen Cycloaddition .” 2013. Web. 15 Apr 2021.

Vancouver:

Moynihan L. Synthesis of Iminosugar C-Glycosides via Tandem Allylic Azide Rearrangement - Huisgen Cycloaddition . [Internet] [Thesis]. National University of Ireland – Galway; 2013. [cited 2021 Apr 15]. Available from: http://hdl.handle.net/10379/4253.

Note: this citation may be lacking information needed for this citation format:
Not specified: Masters Thesis or Doctoral Dissertation

Council of Science Editors:

Moynihan L. Synthesis of Iminosugar C-Glycosides via Tandem Allylic Azide Rearrangement - Huisgen Cycloaddition . [Thesis]. National University of Ireland – Galway; 2013. Available from: http://hdl.handle.net/10379/4253

Note: this citation may be lacking information needed for this citation format:
Not specified: Masters Thesis or Doctoral Dissertation

14. Ferrándiz-Saperas, Marcos. Azomethine Ylides for the Synthesis of Antibiotics, Enantioselective Prolinates and a Graphene-supported Catalyst .

Degree: 2020, University of Alicante

URL: http://hdl.handle.net/10045/109929

► En esta tesis doctoral se ha estudiado la reacción 1,3-dipolar con iluros de azometino y diferentes dipolarófilos para la síntesis de compuestos ópticamente activos, usando… (more)

Subjects/Keywords: 1,3-Dipolar cycloaddition; Diastereoselective; Enantioselective; Pyrrolidine; Proline; Graphene; Catalyst

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APA · Chicago · MLA · Vancouver · CSE | Export to Zotero / EndNote / Reference Manager

APA (6^th Edition):

Ferrándiz-Saperas, M. (2020). Azomethine Ylides for the Synthesis of Antibiotics, Enantioselective Prolinates and a Graphene-supported Catalyst . (Thesis). University of Alicante. Retrieved from http://hdl.handle.net/10045/109929

Note: this citation may be lacking information needed for this citation format:
Not specified: Masters Thesis or Doctoral Dissertation

Chicago Manual of Style (16^th Edition):

Ferrándiz-Saperas, Marcos. “Azomethine Ylides for the Synthesis of Antibiotics, Enantioselective Prolinates and a Graphene-supported Catalyst .” 2020. Thesis, University of Alicante. Accessed April 15, 2021. http://hdl.handle.net/10045/109929.

Note: this citation may be lacking information needed for this citation format:
Not specified: Masters Thesis or Doctoral Dissertation

MLA Handbook (7^th Edition):

Ferrándiz-Saperas, Marcos. “Azomethine Ylides for the Synthesis of Antibiotics, Enantioselective Prolinates and a Graphene-supported Catalyst .” 2020. Web. 15 Apr 2021.

Vancouver:

Ferrándiz-Saperas M. Azomethine Ylides for the Synthesis of Antibiotics, Enantioselective Prolinates and a Graphene-supported Catalyst . [Internet] [Thesis]. University of Alicante; 2020. [cited 2021 Apr 15]. Available from: http://hdl.handle.net/10045/109929.

Note: this citation may be lacking information needed for this citation format:
Not specified: Masters Thesis or Doctoral Dissertation

Council of Science Editors:

Ferrándiz-Saperas M. Azomethine Ylides for the Synthesis of Antibiotics, Enantioselective Prolinates and a Graphene-supported Catalyst . [Thesis]. University of Alicante; 2020. Available from: http://hdl.handle.net/10045/109929

Note: this citation may be lacking information needed for this citation format:
Not specified: Masters Thesis or Doctoral Dissertation

15. Selva, Verónica. Diastereoselective multicomponent [3+2] and [4+2] cycloadditions .

Degree: 2018, University of Alicante

URL: http://hdl.handle.net/10045/77573

► En esta tesis doctoral se ha estudiado los iluros de azometino generados in situ en reacciones de cicloadición 1,3-dipolar y diferentes dipolarófilos para la síntesis… (more)

Subjects/Keywords: Multicomponent; 1,3-Dipolar Cycloaddition; Pyrrolidine; Proline; Diels-Alder; Diastereoselective

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APA · Chicago · MLA · Vancouver · CSE | Export to Zotero / EndNote / Reference Manager

APA (6^th Edition):

Selva, V. (2018). Diastereoselective multicomponent [3+2] and [4+2] cycloadditions . (Thesis). University of Alicante. Retrieved from http://hdl.handle.net/10045/77573

Note: this citation may be lacking information needed for this citation format:
Not specified: Masters Thesis or Doctoral Dissertation

Chicago Manual of Style (16^th Edition):

Selva, Verónica. “Diastereoselective multicomponent [3+2] and [4+2] cycloadditions .” 2018. Thesis, University of Alicante. Accessed April 15, 2021. http://hdl.handle.net/10045/77573.

Note: this citation may be lacking information needed for this citation format:
Not specified: Masters Thesis or Doctoral Dissertation

MLA Handbook (7^th Edition):

Selva, Verónica. “Diastereoselective multicomponent [3+2] and [4+2] cycloadditions .” 2018. Web. 15 Apr 2021.

Vancouver:

Selva V. Diastereoselective multicomponent [3+2] and [4+2] cycloadditions . [Internet] [Thesis]. University of Alicante; 2018. [cited 2021 Apr 15]. Available from: http://hdl.handle.net/10045/77573.

Note: this citation may be lacking information needed for this citation format:
Not specified: Masters Thesis or Doctoral Dissertation

Council of Science Editors:

Selva V. Diastereoselective multicomponent [3+2] and [4+2] cycloadditions . [Thesis]. University of Alicante; 2018. Available from: http://hdl.handle.net/10045/77573

Note: this citation may be lacking information needed for this citation format:
Not specified: Masters Thesis or Doctoral Dissertation

16. Weber, Caroline Sabrina Batista. Avaliação térmica e estrutural de novos cristais líquidos derivados do anel isoxazol.

Degree: 2020, Brazil

URL: http://hdl.handle.net/10183/218964

►

O presente trabalho descreve a síntese e a caracterização de três séries de moléculas na forma banana contendo os anéis isoxazolina e isoxazol. Foram avaliados… (more)

▼

O presente trabalho descreve a síntese e a caracterização de três séries de moléculas na forma banana contendo os anéis isoxazolina e isoxazol. Foram avaliados parâmetros estruturais como o tamanho da cauda e o tipo de núcleo curvo. Metodologias clássicas de síntese foram empregadas na preparação dos compostos finais, sendo a reação de cicloadição [3+2] 1,3-dipolar a etapa chave da rota sintética. A caracterização térmica e estrutural dos compostos foi realizada por MOLP, DSC, DRX e voltagem triangular. Os resultados mostraram que o aumento da cauda nos compostos contendo o anel benzeno como núcleo central e derivados do isoxazol promove a formação de mesofases polares. A mudança do núcleo benzeno para os heterociclos furano e tiofeno em derivados contendo cadeia alquílica composta de oito carbonos não se mostrou uma alternativa promissora, devido à insolubilidade desses compostos e suas altas temperaturas de transição. Todos os intermediários contendo o grupo nitro e o grupo amino derivados do anel isoxazol apresentaram comportamento líquido cristalino, com exceção das estruturas contendo cadeia alquílica composta de apenas um carbono. Os compostos 5e e 7e foram analisados por DRX, permitindo a caracterização da mesofase SmA. A presença do grupo nitro polar promove a formação de fases esméticas interdigitadas, enquanto a presença do grupo amino promove a formação de fases monotrópicas com arranjo em bicamada.

The present work describes the synthesis and characterization of three series of banana shaped molecules containing isoxazoline and isoxazole rings. It was evaluated structural parameters such as the tail size and bent core type. Classical synthetic methodologies were employed in the preparation of the target compounds. The [3+2] 1,3-dipolar cycloaddition was a key step of the synthetic route. Thermal and structural characterization of the compounds was carried out by POM, DSC, XRD and triangular voltage. The results showed that the increase of the tail in the compounds containing the benzene ring as a central core and isoxazole derivatives promotes the formation of the polar mesophases. The change of the benzene core to furan and thiophene heterocycles in derivatives containing alkyl chains of eight carbons did not demonstrated to be a promising alternative, due to the insolubility of these compounds and their high transition temperatures. All intermediates containing nitro and amine groups derived from the isoxazole ring displayed liquid crystalline behavior, except the structures containing alkyl chains with one carbon. The compounds 5e and 7e were analyzed by DRX, enabling the characterization of the SmA mesophase. The presence of the polar nitro group furthers the formation of the interdigitated smetic phases, while the presence amine group furthers the formation of the monotropic phases with bilayer arrangement.

Advisors/Committee Members: Merlo, Aloir Antonio.

Subjects/Keywords: Mesofases; Isoxazol; Cicloadição; Polar mesophases; Isoxazole ring; Dipolar cycloaddition

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APA (6^th Edition):

Weber, C. S. B. (2020). Avaliação térmica e estrutural de novos cristais líquidos derivados do anel isoxazol. (Masters Thesis). Brazil. Retrieved from http://hdl.handle.net/10183/218964

Chicago Manual of Style (16^th Edition):

Weber, Caroline Sabrina Batista. “Avaliação térmica e estrutural de novos cristais líquidos derivados do anel isoxazol.” 2020. Masters Thesis, Brazil. Accessed April 15, 2021. http://hdl.handle.net/10183/218964.

MLA Handbook (7^th Edition):

Weber, Caroline Sabrina Batista. “Avaliação térmica e estrutural de novos cristais líquidos derivados do anel isoxazol.” 2020. Web. 15 Apr 2021.

Vancouver:

Weber CSB. Avaliação térmica e estrutural de novos cristais líquidos derivados do anel isoxazol. [Internet] [Masters thesis]. Brazil; 2020. [cited 2021 Apr 15]. Available from: http://hdl.handle.net/10183/218964.

Council of Science Editors:

Weber CSB. Avaliação térmica e estrutural de novos cristais líquidos derivados do anel isoxazol. [Masters Thesis]. Brazil; 2020. Available from: http://hdl.handle.net/10183/218964

17. Juliana Andreza Figueirôa. Síntese e caracterização de novos compostos mesoiônicos e derivados dos sistemas 1,3-tiazólio-5-tiolato e 1,3-diazólio-5-tiolato.

Degree: 2012, Universidade Federal da Paraíba

URL: http://bdtd.biblioteca.ufpb.br/tde_busca/arquivo.php?codArquivo=2358

►

Os compostos mesoiônicos são heterocíclicos notáveis por apresentar as mais diversas propriedades biológicas, físicas e químicas. São definidos como betaínas heterocíclicas planas e não aromáticas… (more)

▼

Os compostos mesoiônicos são heterocíclicos notáveis por apresentar as mais diversas propriedades biológicas, físicas e químicas. São definidos como betaínas heterocíclicas planas e não aromáticas estabilizadas por deslocalização de elétrons. Através de uma reação in situ de cicloadição/cicloreversão 1,3-dipolar obtiveram-se dois mesoiônicos, MI-1.1 e MI-1.2, através da interconversão do sistema 1,3-oxazólio-5-olato (Munchnonas) para 1,3-tiazólio-5-tiolato. Uma reação de substituição nucleofílica com excesso de iodeto de metila, CH3I, promoveu a primeira modificação no sistema mesoiônico sendo transformados de base livre para sais iodatos S-metilados formando os derivados mesoiônicos, MI-2.1 e MI-2.2. Estes sofreram uma reação de ciclodesidratação na presença de anidrido acético obtendo-se dois mesoiônicos do sistema 1,3-diazólio-5-tiolato, MI-3.1 e MI-3.2, que por sua vez foram alquilados novamente e originaram dois derivados em forma de sais iodatos S-metilados, MI-4.1 e MI-4.2. Sendo os mesoiônicos e seus derivados: MI-2.1, MI-2.2, MI-3.1, MI-3.2, MI-4.1 e MI-4.2 inéditos na literatura. Suas estruturas foram elucidadas por meio de técnicas espectroscópicas de RMN 1H e 13C e infravermelho através de uma análise comparativa com estruturas já existentes.

Mesoionic compounds are notable heterocyclic for having the most diverse biological properties, physical and chemical properties. Are defined as flat and non-aromatic heterocyclic Betaines stabilized by electron delocalization. Through an in situ cycloaddition/cicloreversion 1,3-dipolar were obtained two mesoionic, MI-1.1 and MI-1.2 through of the interconversion system 1,3-oxazólio-5-olato (Munchnonas) for 1,3-tiazólio-5-tiolato. A nucleophilic substitution reaction with excess methyl iodide, CH3I, promoted the first modification to the mesoionic system were changed of free base to iodates salts, S-methylated forming derivatives mesoionic, MI-2.1 e MI-2.2. These underwent a cyclodehydration reaction in the presence of acetic anhydride yielding two mesoionic system 1,3-diazolium-5-thiolate, MI-3.1 and MI-3.2, which in turn were alkylated again and originated two derived in the form of iodates salts S-methylated, MI-4.1 and MI-4.2. As the mesoionic and its derivatives: MI-2.1, MI-2.2, MI-3.1, MI-3.2, MI-4.1 and MI-4.2 and unpublished literature. Their structures were elucidated by spectroscopic techniques for RMN 1H and 13C and infrared light through a comparative analysis with existing structures.

Advisors/Committee Members: Bruno Freitas Lira, Petrônio Filqueiras de Athayde Filho.

Subjects/Keywords: técnicas espectroscópias; Reações de cicloadição/reversão 1,3-dipolar; Compostos mesoiônicos; QUIMICA; Mesoionic Compounds; Cycloaddition Reactions / Cycloreversion 1,3-dipolar; Spectroscopic techniques

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APA · Chicago · MLA · Vancouver · CSE | Export to Zotero / EndNote / Reference Manager

APA (6^th Edition):

Figueirôa, J. A. (2012). Síntese e caracterização de novos compostos mesoiônicos e derivados dos sistemas 1,3-tiazólio-5-tiolato e 1,3-diazólio-5-tiolato. (Thesis). Universidade Federal da Paraíba. Retrieved from http://bdtd.biblioteca.ufpb.br/tde_busca/arquivo.php?codArquivo=2358

Note: this citation may be lacking information needed for this citation format:
Not specified: Masters Thesis or Doctoral Dissertation

Chicago Manual of Style (16^th Edition):

Figueirôa, Juliana Andreza. “Síntese e caracterização de novos compostos mesoiônicos e derivados dos sistemas 1,3-tiazólio-5-tiolato e 1,3-diazólio-5-tiolato.” 2012. Thesis, Universidade Federal da Paraíba. Accessed April 15, 2021. http://bdtd.biblioteca.ufpb.br/tde_busca/arquivo.php?codArquivo=2358.

Note: this citation may be lacking information needed for this citation format:
Not specified: Masters Thesis or Doctoral Dissertation

MLA Handbook (7^th Edition):

Figueirôa, Juliana Andreza. “Síntese e caracterização de novos compostos mesoiônicos e derivados dos sistemas 1,3-tiazólio-5-tiolato e 1,3-diazólio-5-tiolato.” 2012. Web. 15 Apr 2021.

Vancouver:

Figueirôa JA. Síntese e caracterização de novos compostos mesoiônicos e derivados dos sistemas 1,3-tiazólio-5-tiolato e 1,3-diazólio-5-tiolato. [Internet] [Thesis]. Universidade Federal da Paraíba; 2012. [cited 2021 Apr 15]. Available from: http://bdtd.biblioteca.ufpb.br/tde_busca/arquivo.php?codArquivo=2358.

Note: this citation may be lacking information needed for this citation format:
Not specified: Masters Thesis or Doctoral Dissertation

Council of Science Editors:

Figueirôa JA. Síntese e caracterização de novos compostos mesoiônicos e derivados dos sistemas 1,3-tiazólio-5-tiolato e 1,3-diazólio-5-tiolato. [Thesis]. Universidade Federal da Paraíba; 2012. Available from: http://bdtd.biblioteca.ufpb.br/tde_busca/arquivo.php?codArquivo=2358

Note: this citation may be lacking information needed for this citation format:
Not specified: Masters Thesis or Doctoral Dissertation

18. Moraes, Maiara Correa de. Síntese de 1h-1,2,3-triazóis trialoacetil substituídos análogos estruturais da rufinamida.

Degree: 2013, Universidade Federal de Santa Maria; Programa de Pós-Graduação em Química; UFSM; BR; Química

URL: http://repositorio.ufsm.br/handle/1/10538

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Coordenação de Aperfeiçoamento de Pessoal de Nível Superior

The present dissertation describes a chemical methodology for the synthesis of three series containing fourteen new molecules… (more)

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Coordenação de Aperfeiçoamento de Pessoal de Nível Superior

The present dissertation describes a chemical methodology for the synthesis of three series containing fourteen new molecules of trifluoro(chloro)methyl substituted 1H-1,2,3-triazoles, which are structural analogues to the antiepileptic drug Rufinamide. The protocol used consisted in reactions of 1,3-dipolar cycloaddition of 2,6-difluorobenzyl azide and 4-alkoxy-4-alkyl(aryl/heteroaryl)-1,1,1-trifluoro(chloro)-3-alken-2-ones, where the 4-substituents are H, Me, Ph, 4-OMeC6H4, 4-NO2C6H4,4-FC6H4,2-Thienyle 4,4 -Biphenyl. The optimized reactios were carried-out in absense of solvente, in reaction times of 48 to 96 hours at 100-150°C and in yields of 30-75%. The reactions employing the 4-alkoxy-4-aryl(heteroaryl)-1,1,1-trifluoro-3-alken-2-ones 1and 2,6-difluorobenzyl azidedemonstrated a 4-substituent dependency of the enones precursors (above mentioned) and conducted to the formation of isomeric mixtures of 4-trifluoroacetyl substituted and/or 5-trifluoromethyl substituted triazoles in varying proportions, which were separated and purified by chromatographic columns. On the other hand, the reactions employing the 4-alkoxy-4-alkyl(aryl/heteroaryl)-1,1,1-trichloro-3-alken-2-ones and the same 2,6-difluorobenzyl azide produced exclusively a series of 4- trichloroacetyl substituted triazoles without the detection of the respective 5-trichloromethyl substituted regioisomer. The synthesized triazoles were characterized by 1H, 13C, uni- and two-dimensional NMR Spectroscopy techniques as HMQC, gas chromatography coupled to mass spectrometry (GC-MS), mono-crystal X-ray diffraction, high resolution mass spectrometry (HRMS) and their purity determined by CHN Elemental Analysis.

A presente dissertação descreve uma metodologia química para a síntese de três séries de 1H-1,2,3-triazóis trifluor(cloro)metil substituídos, totalizando quatorze moléculas inéditas, as quais são análogas estruturais do fármaco antiepiléptico Rufinamida. O protocolo consistiu na realização de reações de cicloadição 1,3-dipolares envolvendo 2,6-difluorbenzil azida e 4-alcóxi-4-alquil(aril/heteroaril)-1,1,1-trifluor(cloro)-3-alquen-2-onas, sendo os substituintes 4-alquila(arila/heteroarila) iguais a H, Me, Ph, 4-OMeC6H4, 4-NO2C6H4,4-FC6H4,2-Tienila e 4,4 -Bifenila. As reações otimizadas se processaram na ausência de solvente, em tempos reacionais de 48 a 96 horas a 100-150°C e levaram a rendimentos na faixa de 30-75%. As reações que utilizaram 4-alcóxi-4-aril(heteroaril)-1,1,1-triflúor-3-alquen-2-onase 2,6-difluorbenzil azida apresentaram uma dependência quanto a substituição da posição 4 das enonas precursoras (acima descritos) e conduziram à formação de misturas isoméricas de triazóis 4-trifluoracetil substituídos e/ou 5-trifluormetil substituídos em proporções variadas, as quais foram passíveis de separação e purificação por cromatografia em coluna. Por outro lado, as reações empregando 4-alcóxi-4-alquil(aril/heteroaril)-1,1,1-tricloro-3-alquen-2-onas e a mesma 2,6-difluorbenzil azida…

Advisors/Committee Members: Bonacorso, Helio Gauze, Braibante, Mara Elisa Fortes, Campos, Patrick Teixeira.

Subjects/Keywords: 1H-1,2,3-triazóis; Cicloadição 1,3-dipolar; Rufinamida; 1H-1,2,3-triazoles; 1,3-dipolar cycloaddition; Rufinamide; CNPQ::CIENCIAS EXATAS E DA TERRA::QUIMICA

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APA · Chicago · MLA · Vancouver · CSE | Export to Zotero / EndNote / Reference Manager

APA (6^th Edition):

Moraes, M. C. d. (2013). Síntese de 1h-1,2,3-triazóis trialoacetil substituídos análogos estruturais da rufinamida. (Masters Thesis). Universidade Federal de Santa Maria; Programa de Pós-Graduação em Química; UFSM; BR; Química. Retrieved from http://repositorio.ufsm.br/handle/1/10538

Chicago Manual of Style (16^th Edition):

Moraes, Maiara Correa de. “Síntese de 1h-1,2,3-triazóis trialoacetil substituídos análogos estruturais da rufinamida.” 2013. Masters Thesis, Universidade Federal de Santa Maria; Programa de Pós-Graduação em Química; UFSM; BR; Química. Accessed April 15, 2021. http://repositorio.ufsm.br/handle/1/10538.

MLA Handbook (7^th Edition):

Moraes, Maiara Correa de. “Síntese de 1h-1,2,3-triazóis trialoacetil substituídos análogos estruturais da rufinamida.” 2013. Web. 15 Apr 2021.

Vancouver:

Moraes MCd. Síntese de 1h-1,2,3-triazóis trialoacetil substituídos análogos estruturais da rufinamida. [Internet] [Masters thesis]. Universidade Federal de Santa Maria; Programa de Pós-Graduação em Química; UFSM; BR; Química; 2013. [cited 2021 Apr 15]. Available from: http://repositorio.ufsm.br/handle/1/10538.

Council of Science Editors:

Moraes MCd. Síntese de 1h-1,2,3-triazóis trialoacetil substituídos análogos estruturais da rufinamida. [Masters Thesis]. Universidade Federal de Santa Maria; Programa de Pós-Graduação em Química; UFSM; BR; Química; 2013. Available from: http://repositorio.ufsm.br/handle/1/10538

19. Seingeot, Adeline. Utilisation des liquides ioniques dans des réactions à économies d'atomes : l'addition de Michael et la cycloaddition 1,3-dipolaire : Use of ionic liquids in atom economy reactions : the Michael addition and the 1,3-dipolar cycloaddition.

Degree: Docteur es, Chimie organique, chimie du vivant, 2011, Aix-Marseille 3

URL: http://www.theses.fr/2011AIX30058

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L'une des préoccupations de la chimie moderne est de développer des procédés éco-compatibles : une tendance consiste à remplacer les solvants organiques par les Liquides… (more)

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L'une des préoccupations de la chimie moderne est de développer des procédés éco-compatibles : une tendance consiste à remplacer les solvants organiques par les Liquides Ioniques (LI). Ainsi ces travaux décrivent l'utilisation des LI dans deux réactions à économie d'atomes : l'addition de Michael et la réaction de cycloaddition 1,3-dipolaire catalysée (ou non) par un sel de cuivre (CuAAC). La première partie des travaux relate l'emploi de Liquides Ioniques Super-Acides (LISA), connus pour générer une activation électrophile. Une optimisation du LISA a été effectuée sur une réaction-modèle, puis l'application à d'autres électrophiles et nucléophiles a été étudiée. La pureté du LISA influe sur la chimiosélectivité : s’il est partiellement hydrolysé, la réaction d'annélation de Robinson devient prépondérante. La version asymétrique du processus a été abordée, montrant qu'il est possible d'obtenir un excès énantiomérique à partir de dérivés d'acides aminés. La seconde partie de l'étude a permis de mettre au point une synthèse de (triazolylméthyl)vinylphosphonates à partir d'un acétoxyméthylvinylphosphonate selon une procédure monotope reposant sur la cycloaddition 1,3-dipolaire dans différents LI. Nous avons ensuite montré que le LI joue aussi le rôle d'activateur pour cette réaction.

In the context of sustainable chemistry, an alternative to conventional organic solvents is the use of ionic liquids. These works reported here aims to describe the use of ionic liquids (IL) in two atoms economy reactions, namely the Michael addition reaction and 1,3-dipolar cycloaddition catalyzed (or not) by a copper salt (CuAAC). In the first part of the work reports the use of Super-Acid Ionic Liquids (SAIL), which initiate an electrophilic activation. After optimization of SAIL on a reaction model, application to other electrophiles and nucleophiles is discussed. The purity of SAIL affects the chemioselectivity: if the SAIL is partially hydrolyzed, a Robinson annulation predominates. The asymmetric version of the process is investigated, showing that it is possible to carry out an enantioselective reaction with amino acid derived SAIL. The second part of the study deals with setting up an original synthesis of (triazolylmethyl)vinylphosphonate from acetoxymethylvinylphosphonate using a one-pot procedure involving a 1,3-dipolar cycloaddition in different LI. We further showed that the ionic liquid can also act as an activator for this reaction.

Advisors/Committee Members: Maffei, Michel (thesis director), Anguille, Stéphane (thesis director).

Subjects/Keywords: Liquides ioniques; Cycloaddition 1,3-dipolaire; (triazolylméthyl)vinylphosphonates; CuAAC; Addition de Michael; Ionic liquids; Michael Addition; 1,3-dipolar cycloaddition; (triazolylmethyl)vinylphosphonates; CuAAC

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APA · Chicago · MLA · Vancouver · CSE | Export to Zotero / EndNote / Reference Manager

APA (6^th Edition):

Seingeot, A. (2011). Utilisation des liquides ioniques dans des réactions à économies d'atomes : l'addition de Michael et la cycloaddition 1,3-dipolaire : Use of ionic liquids in atom economy reactions : the Michael addition and the 1,3-dipolar cycloaddition. (Doctoral Dissertation). Aix-Marseille 3. Retrieved from http://www.theses.fr/2011AIX30058

Chicago Manual of Style (16^th Edition):

Seingeot, Adeline. “Utilisation des liquides ioniques dans des réactions à économies d'atomes : l'addition de Michael et la cycloaddition 1,3-dipolaire : Use of ionic liquids in atom economy reactions : the Michael addition and the 1,3-dipolar cycloaddition.” 2011. Doctoral Dissertation, Aix-Marseille 3. Accessed April 15, 2021. http://www.theses.fr/2011AIX30058.

MLA Handbook (7^th Edition):

Seingeot, Adeline. “Utilisation des liquides ioniques dans des réactions à économies d'atomes : l'addition de Michael et la cycloaddition 1,3-dipolaire : Use of ionic liquids in atom economy reactions : the Michael addition and the 1,3-dipolar cycloaddition.” 2011. Web. 15 Apr 2021.

Vancouver:

Seingeot A. Utilisation des liquides ioniques dans des réactions à économies d'atomes : l'addition de Michael et la cycloaddition 1,3-dipolaire : Use of ionic liquids in atom economy reactions : the Michael addition and the 1,3-dipolar cycloaddition. [Internet] [Doctoral dissertation]. Aix-Marseille 3; 2011. [cited 2021 Apr 15]. Available from: http://www.theses.fr/2011AIX30058.

Council of Science Editors:

Seingeot A. Utilisation des liquides ioniques dans des réactions à économies d'atomes : l'addition de Michael et la cycloaddition 1,3-dipolaire : Use of ionic liquids in atom economy reactions : the Michael addition and the 1,3-dipolar cycloaddition. [Doctoral Dissertation]. Aix-Marseille 3; 2011. Available from: http://www.theses.fr/2011AIX30058

20. Favre, Camille. Novel bioorthogonal chemical reporters and fluorogenic probes for biomolecules imaging : Nouveaux rapporteurs chimiques et sondes fluorogènes bioorthogonaux pour l'imagerie de biomolécules.

Degree: Docteur es, Interface Chimie Biologie, 2019, Bordeaux

URL: http://www.theses.fr/2019BORD0079

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L'imagerie de biomolécules, et plus particulièrement des glycanes, au sein d'organismes vivants, représente un incroyable challenge. Cependant, des progrès significatifs ont été réalisés ces dix… (more)

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L'imagerie de biomolécules, et plus particulièrement des glycanes, au sein d'organismes vivants, représente un incroyable challenge. Cependant, des progrès significatifs ont été réalisés ces dix dernières années grâce au développement de la stratégie du rapporteur chimique bioorthogonal. Cette technique implique, dans un premier temps, l'incorporation d'une fonctionnalité chimique non native (rapporteur) au sein de biomolécules complexes. Ce rapporteur peut ensuite réagir sélectivement avec une sonde moléculaire spécifique permettant ainsi la détection de la biomolécule ciblée. Afin d'imager ces biomolécules en temps réel, les sondes fluorogènes, des réactifs non fluorescents qui deviennent fluorescents après réaction avec le rapporteur chimique, ont été récemment développées. Ces dernières années, la cycloaddition 1,3-dipolaire sans métaux, entre les cylooctynes et les azotures, a été élégamment employée comme réaction bioorthogonale pour l'imagerie de biomolécules au sein d'organismes vivants. Cependant, l'azoture présente certaines limitations, notamment il peut être réduit par les thiols cellulaires. En conséquence, nous avons étudié l'utilisation de 1,3-dipôles plus stables, en tant que nouveaux rapporteurs chimiques bioorthogonaux pour l'imagerie de biomolécules par fluorescence. De plus, nous avons aussi développé de nouvelles sondes fluorogènes bioorthogonales ayant de bonnes propriétés de fluorescence, telles que de hautes valeurs de rendement quantique et des longueurs d'ondes d'émission déplacées dans le rouge, pour une potentielle application chez l'animal.

Imaging biomolecules, such as glycans, in living systems remains a formidable chemical challenge. However, significant progress has been made over the past ten years, with the ground-breaking development of the bioorthogonal chemical reporter strategy. In this context, complex biomolecules are fitted with a non-native chemical functionality (reporter) that can react selectively with a complementary bioorthogonal probe for detection. In order to image these biomolecules in real time, fluorogenic probes, non fluorescent reagents that produce highly fluorescent products, have recently been developed. This last decade, the metal-free 1,3-dipolar cycloaddition between cyclooctynes and azides have been elegantly employed for biomolecules imaging in living systems. However, azides suffer from limitations such as their reduction by endogenous cellular thiols. Consequently, we have investigated the use of more stable 1,3-dipoles as new chemical reporters for fluorescent biomolecule imaging. In addition, we also developed novel bioorthogonal fluorogenic probes with improved fluorescence properties such as high quantum yields and red-shifted fluorescence emission for potential applications in living animals.

Advisors/Committee Members: Friscourt, Frédéric (thesis director).

Subjects/Keywords: Chimie bioorthogonale; Sondes fluorogènes; Cycloaddition 1.3-Dipolaire; Cyclooctynes; Composés mésoioniques; Bioorthogonal chemistry; Fluorogenic probes; 1.3-Dipolar cycloaddition; Cyclooctynes; Meosionic compounds

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APA · Chicago · MLA · Vancouver · CSE | Export to Zotero / EndNote / Reference Manager

APA (6^th Edition):

Favre, C. (2019). Novel bioorthogonal chemical reporters and fluorogenic probes for biomolecules imaging : Nouveaux rapporteurs chimiques et sondes fluorogènes bioorthogonaux pour l'imagerie de biomolécules. (Doctoral Dissertation). Bordeaux. Retrieved from http://www.theses.fr/2019BORD0079

Chicago Manual of Style (16^th Edition):

Favre, Camille. “Novel bioorthogonal chemical reporters and fluorogenic probes for biomolecules imaging : Nouveaux rapporteurs chimiques et sondes fluorogènes bioorthogonaux pour l'imagerie de biomolécules.” 2019. Doctoral Dissertation, Bordeaux. Accessed April 15, 2021. http://www.theses.fr/2019BORD0079.

MLA Handbook (7^th Edition):

Favre, Camille. “Novel bioorthogonal chemical reporters and fluorogenic probes for biomolecules imaging : Nouveaux rapporteurs chimiques et sondes fluorogènes bioorthogonaux pour l'imagerie de biomolécules.” 2019. Web. 15 Apr 2021.

Vancouver:

Favre C. Novel bioorthogonal chemical reporters and fluorogenic probes for biomolecules imaging : Nouveaux rapporteurs chimiques et sondes fluorogènes bioorthogonaux pour l'imagerie de biomolécules. [Internet] [Doctoral dissertation]. Bordeaux; 2019. [cited 2021 Apr 15]. Available from: http://www.theses.fr/2019BORD0079.

Council of Science Editors:

Favre C. Novel bioorthogonal chemical reporters and fluorogenic probes for biomolecules imaging : Nouveaux rapporteurs chimiques et sondes fluorogènes bioorthogonaux pour l'imagerie de biomolécules. [Doctoral Dissertation]. Bordeaux; 2019. Available from: http://www.theses.fr/2019BORD0079

Texas A&M University

21. Kang, Jun Yong. Synthesis of 5-Substituted Isoxazolidines by [3 plus 2] Cycloaddition of Nitrones Generated in an Unusual Way from Nitrosobenzene and Styrene.

Degree: MS, Chemistry, 2010, Texas A&M University

URL: http://hdl.handle.net/1969.1/ETD-TAMU-2008-12-82

► A new synthetic method toward 5-substituted isoxazolidines by [3 plus 2] cycloaddition of nitrones generated from nitrosobenzene and styrene was discovered. The formation of nitrones… (more)

Subjects/Keywords: [3+2] dipolar cycloaddition; isoxazolidine; nitrone

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APA · Chicago · MLA · Vancouver · CSE | Export to Zotero / EndNote / Reference Manager

APA (6^th Edition):

Kang, J. Y. (2010). Synthesis of 5-Substituted Isoxazolidines by [3 plus 2] Cycloaddition of Nitrones Generated in an Unusual Way from Nitrosobenzene and Styrene. (Masters Thesis). Texas A&M University. Retrieved from http://hdl.handle.net/1969.1/ETD-TAMU-2008-12-82

Chicago Manual of Style (16^th Edition):

Kang, Jun Yong. “Synthesis of 5-Substituted Isoxazolidines by [3 plus 2] Cycloaddition of Nitrones Generated in an Unusual Way from Nitrosobenzene and Styrene.” 2010. Masters Thesis, Texas A&M University. Accessed April 15, 2021. http://hdl.handle.net/1969.1/ETD-TAMU-2008-12-82.

MLA Handbook (7^th Edition):

Kang, Jun Yong. “Synthesis of 5-Substituted Isoxazolidines by [3 plus 2] Cycloaddition of Nitrones Generated in an Unusual Way from Nitrosobenzene and Styrene.” 2010. Web. 15 Apr 2021.

Vancouver:

Kang JY. Synthesis of 5-Substituted Isoxazolidines by [3 plus 2] Cycloaddition of Nitrones Generated in an Unusual Way from Nitrosobenzene and Styrene. [Internet] [Masters thesis]. Texas A&M University; 2010. [cited 2021 Apr 15]. Available from: http://hdl.handle.net/1969.1/ETD-TAMU-2008-12-82.

Council of Science Editors:

Kang JY. Synthesis of 5-Substituted Isoxazolidines by [3 plus 2] Cycloaddition of Nitrones Generated in an Unusual Way from Nitrosobenzene and Styrene. [Masters Thesis]. Texas A&M University; 2010. Available from: http://hdl.handle.net/1969.1/ETD-TAMU-2008-12-82

University of Vermont

22. Liu, Xiaoxi. Novel Aza-Prins Cyclization and [3+2] Dipolar Cycloaddition Toward N-Heterocyclic Molecules and Studies Toward the Total Synthesis of Borrecapine.

Degree: PhD, Chemistry, 2014, University of Vermont

URL: https://scholarworks.uvm.edu/graddis/310

► Highly functionalized 5 or 6-membered nitrogen-containing heterocyclic moieties are highly prevalent in pharmaceuticals reagents, alkaloid natural products, organocatalysts, as well as useful building blocks… (more)

Subjects/Keywords: [3+2] dipolar cycloaddition; aza-Prins; camphorsulfonic acid; formaldehyde; sulfonyl; vinyl pyrrolidine; Chemistry

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APA · Chicago · MLA · Vancouver · CSE | Export to Zotero / EndNote / Reference Manager

APA (6^th Edition):

Liu, X. (2014). Novel Aza-Prins Cyclization and [3+2] Dipolar Cycloaddition Toward N-Heterocyclic Molecules and Studies Toward the Total Synthesis of Borrecapine. (Doctoral Dissertation). University of Vermont. Retrieved from https://scholarworks.uvm.edu/graddis/310

Chicago Manual of Style (16^th Edition):

Liu, Xiaoxi. “Novel Aza-Prins Cyclization and [3+2] Dipolar Cycloaddition Toward N-Heterocyclic Molecules and Studies Toward the Total Synthesis of Borrecapine.” 2014. Doctoral Dissertation, University of Vermont. Accessed April 15, 2021. https://scholarworks.uvm.edu/graddis/310.

MLA Handbook (7^th Edition):

Liu, Xiaoxi. “Novel Aza-Prins Cyclization and [3+2] Dipolar Cycloaddition Toward N-Heterocyclic Molecules and Studies Toward the Total Synthesis of Borrecapine.” 2014. Web. 15 Apr 2021.

Vancouver:

Liu X. Novel Aza-Prins Cyclization and [3+2] Dipolar Cycloaddition Toward N-Heterocyclic Molecules and Studies Toward the Total Synthesis of Borrecapine. [Internet] [Doctoral dissertation]. University of Vermont; 2014. [cited 2021 Apr 15]. Available from: https://scholarworks.uvm.edu/graddis/310.

Council of Science Editors:

Liu X. Novel Aza-Prins Cyclization and [3+2] Dipolar Cycloaddition Toward N-Heterocyclic Molecules and Studies Toward the Total Synthesis of Borrecapine. [Doctoral Dissertation]. University of Vermont; 2014. Available from: https://scholarworks.uvm.edu/graddis/310

University of Guelph

23. Nagireddy, Jaipal. Synthesis and Ring-Opening Reactions of Bicyclic Alkene-Fused Isoxazolines.

Degree: PhD, Department of Chemistry, 2014, University of Guelph

URL: https://atrium.lib.uoguelph.ca/xmlui/handle/10214/8605

► This thesis is an investigation of 1,3-dipolar cycloaddition reactions of nitrile oxides with symmetrical and unsymmetrical bicyclic alkenes, and their subsequent isoxazoline ring opening reactions.… (more)

▼ This thesis is an investigation of 1,3-dipolar cycloaddition reactions of nitrile oxides with symmetrical and unsymmetrical bicyclic alkenes, and their subsequent isoxazoline ring opening reactions. Although a large number of 1,3-dipolar cycloaddition reactions between nitrile oxides and bicyclic alkenes have been reported, most of these are currently limited to carbobicyclic alkenes. Introduction of a heteroatom in the bicyclic ring offers differences in the reactivity and selectivity of cycloaddition reactions. Introduction of a substituent at the bridgehead carbon of the bicycloalkene makes the molecule unsymmetrical. The implications of the reduction of symmetry in C1-substituted heterobicyclic rings open the door to regioselectivity studies for these cycloaddition reactions. The stereo- and regiochemical aspects of 1,3-dipolar cycloaddition reactions with acetonitrile oxide and benzonitrile oxide were examined on a wide variety of symmetrical and unsymmetrical oxabicyclic and azabicyclic alkenes. The cycloadditions were found to be completely stereoselective producing only the exo adducts in moderate to excellent yields. In the majority of the cycloaddition reactions, both of the possible regioisomers were produced in varying ratios that depended on electronic and steric effects of the C1 substituent. After having generated numerous isoxazoline derivatives, various metal-catalyzed (Mo, Pd, Zn, Fe and Ni) cleavage conditions were investigated, with successful N-O bond cleavage of isoxazoline rings achieved using Raney-Ni/AlCl3. An N-O bond cleavage, followed by an imine hydrolysis led to the formation of a variety of novel β-hydroxyketone products with moderate to excellent yields. In the early part of this project, a simple and scalable procedure for the preparation of 2-bromofuran was developed. 2-Bromofuran was found to be useful for preparing a series of 2-aryl furans using the Suzuki cross coupling reaction with arylboronic acids. Similarly 2-alkyl furans were prepared using an iron catalyzed cross coupling reaction between 2-bromofuran and alkyl Grignard reagents. The 2-substituted furans were used for the preparation of various C1-substituted oxabicyclic alkenes via the Diels-Alder cycloaddition strategy. Advisors/Committee Members: Tam, William (advisor).

Subjects/Keywords: 1,3-Dipolar cycloaddition; Isoxazoline ring opening; Oxabicyclic alkene fused isoxazolines; azabicyclic alkene fused isoxazolines

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APA · Chicago · MLA · Vancouver · CSE | Export to Zotero / EndNote / Reference Manager

APA (6^th Edition):

Nagireddy, J. (2014). Synthesis and Ring-Opening Reactions of Bicyclic Alkene-Fused Isoxazolines. (Doctoral Dissertation). University of Guelph. Retrieved from https://atrium.lib.uoguelph.ca/xmlui/handle/10214/8605

Chicago Manual of Style (16^th Edition):

Nagireddy, Jaipal. “Synthesis and Ring-Opening Reactions of Bicyclic Alkene-Fused Isoxazolines.” 2014. Doctoral Dissertation, University of Guelph. Accessed April 15, 2021. https://atrium.lib.uoguelph.ca/xmlui/handle/10214/8605.

MLA Handbook (7^th Edition):

Nagireddy, Jaipal. “Synthesis and Ring-Opening Reactions of Bicyclic Alkene-Fused Isoxazolines.” 2014. Web. 15 Apr 2021.

Vancouver:

Nagireddy J. Synthesis and Ring-Opening Reactions of Bicyclic Alkene-Fused Isoxazolines. [Internet] [Doctoral dissertation]. University of Guelph; 2014. [cited 2021 Apr 15]. Available from: https://atrium.lib.uoguelph.ca/xmlui/handle/10214/8605.

Council of Science Editors:

Nagireddy J. Synthesis and Ring-Opening Reactions of Bicyclic Alkene-Fused Isoxazolines. [Doctoral Dissertation]. University of Guelph; 2014. Available from: https://atrium.lib.uoguelph.ca/xmlui/handle/10214/8605

Freie Universität Berlin

24. Ahsanullah, . 1,3-dipolare Cycloaddition zwischen Aziden und Phosphoranen und deren Verwendung in Peptidligation.

Degree: 2011, Freie Universität Berlin

URL: http://dx.doi.org/10.17169/refubium-7218

► Ziel dieses arbeit war der Integration der Triazolligation in die Fmoc- basierte Peptidsynthese und die Entwicklung einer biokompatiblen Triazolliagtion. Zu diesem Zweck wurden polymergebundene Phosphorane,… (more)

▼ Ziel dieses arbeit war der Integration der Triazolligation in die Fmoc- basierte Peptidsynthese und die Entwicklung einer biokompatiblen Triazolliagtion. Zu diesem Zweck wurden polymergebundene Phosphorane, die bereits in der Festphasenpeptidsynthese für C-terminale Variationen von Peptiden in unserer Gruppe angewandt worden ist, für die Synthese von Peptidylphosphoranen verwendet. In dieser Dissertation ist die Anwendung der Peptidylphosphorane als Dipol bei 1,3-dipolaren Cycloadditionen mit Aziden beschrieben. Polymer-unterstütztes Phosphoranylidenacetat wurde durch Alkylierung mit tert-Butyl-essigester und anschließender Deprotonierung mit Triethylamin erhalten. Das festphasen-gebundene Wittigylid wurde für eine razemisierungsfreie C-C Acylierung und eine weitere Festphasenpeptidsynthese (SPPS) erfolgreich verwendet. Nach Acetylierung oder Einführung einer Azido- gruppe am N-Terminus wurde die tert-Butyl-Schutzgruppe mit TFA abgespalten. Nach der Esterabspaltung und anschließender Decarboxylierung wurden.Peptidylphosphorane oder Azidophosphorane erhalten Das Peptidylphosphoran wurde mit elektronenarmen Aziden wie Trifluoroacetylazid, Tosylazid, 4-Nitrobenzylazid und Carboxylphenylazid in unpolaren Lösungsmitteln bei Raumtemperatur regioselektiv zu 1,5-disubstituierten Triazolen umgesetzt. Bei elektronenreichen Aziden wie Benzylazid, Methyl-2-azidoacetat und 2-Azidoacetamid konnten 1,5-disubstituierte Triazole synthetisiert werden, allerdings unter Anwendung von polaren Lösungsmitteln bei 60°C. Letztendlich wurde diese Reaktion für kurze Peptidligationen durch Erhitzen von Peptidylphosphoranen mit Azidopeptiden in polaren Lösungsmitteln wie THF oder DMF verwendet. Das Potential der Ligationsprodukte mit eingebauten 1,5-Triazolen stabile Konformationen in Lösung zu bilden wurde unter Anwendung der 2D-ROESY-Spektroscopie und die Molekulare Dynamische Simulation untersucht. Die Azido-Peptidyl-Phosphorane wurden durch die cyclische Spaltung zu Tirazolyl-zyklopeptiden umgesetzt. Wenn Azido-dipeptidyl Phosphorane in DMF erhitzt werden, reagieren sie zu Dimeren. Im Gegensatz dazu, durch die Konkurenz zwischen intra-gegen inter-zentrenreaktionen, die Azido-tripeptidyl phophorane führten zu einer Mischung aus monomeren und dimeren Triazolyl-zyklopeptiden. Ein rigideres macroporöses Harz mit höherer prozentualer Quervernetzung (20% DVB) wurde hier anstatt der bis jetzt benutzten mikroporöser Harz verwendet, um die interzentrenreaktionen zu vermeiden und eine höher Verschiebung der Reaktion Richtung des monomeren Produktes im Falle des Azido-tripeptidylphosphorans. Azido- dipeptidylphosphorane wurden unter Anwendung des makroporösen Harz in der dimeren Form erhalten. Unsere Beobachtungen zeigen, dass Azido-dipeptide zu kurz für eine zyklische Abspaltung sind. In diesem Fall ist außerdem die interzentrenreaktion streng bevorzugt. Azido tetra-, penta- und octa-peptidyl- phosphorane wurden wie erwartet als monomere Triazolyl-zyklopeptide erhalten. Die oben beschriebene Festphasensynthese wurde auch in Lösung durchgeführt, um die… Advisors/Committee Members: [email protected] (contact), m (gender), Prof. Dr. Hans-Ulrich Reissig (firstReferee), Prof. Dr. Jörg Rademann (furtherReferee).

Subjects/Keywords: 1; 3-Dipolar cycloaddition; Triazoles; Peptide Ligation; Peptidomimetics; Phosphoranes; Biocompatible reactions; 500 Naturwissenschaften und Mathematik

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APA · Chicago · MLA · Vancouver · CSE | Export to Zotero / EndNote / Reference Manager

APA (6^th Edition):

Ahsanullah, .. (2011). 1,3-dipolare Cycloaddition zwischen Aziden und Phosphoranen und deren Verwendung in Peptidligation. (Thesis). Freie Universität Berlin. Retrieved from http://dx.doi.org/10.17169/refubium-7218

Note: this citation may be lacking information needed for this citation format:
Author name may be incomplete
Not specified: Masters Thesis or Doctoral Dissertation

Chicago Manual of Style (16^th Edition):

Ahsanullah, .. “1,3-dipolare Cycloaddition zwischen Aziden und Phosphoranen und deren Verwendung in Peptidligation.” 2011. Thesis, Freie Universität Berlin. Accessed April 15, 2021. http://dx.doi.org/10.17169/refubium-7218.

Note: this citation may be lacking information needed for this citation format:
Author name may be incomplete
Not specified: Masters Thesis or Doctoral Dissertation

MLA Handbook (7^th Edition):

Ahsanullah, .. “1,3-dipolare Cycloaddition zwischen Aziden und Phosphoranen und deren Verwendung in Peptidligation.” 2011. Web. 15 Apr 2021.

Note: this citation may be lacking information needed for this citation format:
Author name may be incomplete

Vancouver:

Ahsanullah, .. 1,3-dipolare Cycloaddition zwischen Aziden und Phosphoranen und deren Verwendung in Peptidligation. [Internet] [Thesis]. Freie Universität Berlin; 2011. [cited 2021 Apr 15]. Available from: http://dx.doi.org/10.17169/refubium-7218.

Note: this citation may be lacking information needed for this citation format:
Author name may be incomplete
Not specified: Masters Thesis or Doctoral Dissertation

Council of Science Editors:

Ahsanullah, .. 1,3-dipolare Cycloaddition zwischen Aziden und Phosphoranen und deren Verwendung in Peptidligation. [Thesis]. Freie Universität Berlin; 2011. Available from: http://dx.doi.org/10.17169/refubium-7218

Note: this citation may be lacking information needed for this citation format:
Author name may be incomplete
Not specified: Masters Thesis or Doctoral Dissertation

University of Lund

25. Peterson, Kristoffer. Molecular basis for galectin-ligand interactions : Design, synthesis and analysis of ligands.

Degree: 2018, University of Lund

URL: https://lup.lub.lu.se/record/777b2fa7-2293-453b-9771-0f0ab6f6a6d2 ; https://portal.research.lu.se/ws/files/38414625/Thesis.pdf

► Galectins are a class of β-galactoside-binding proteins that bind glycoconjugates and have been implicated in cancer, regulation of immunity and inflammation. Design and synthesis have… (more)

Subjects/Keywords: Organic Chemistry; Galectin; Structure-based design; Thiodigalactoside; Huisgen 1,3-dipolar cycloaddition; Protein-ligand binding interactions

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APA · Chicago · MLA · Vancouver · CSE | Export to Zotero / EndNote / Reference Manager

APA (6^th Edition):

Peterson, K. (2018). Molecular basis for galectin-ligand interactions : Design, synthesis and analysis of ligands. (Doctoral Dissertation). University of Lund. Retrieved from https://lup.lub.lu.se/record/777b2fa7-2293-453b-9771-0f0ab6f6a6d2 ; https://portal.research.lu.se/ws/files/38414625/Thesis.pdf

Chicago Manual of Style (16^th Edition):

Peterson, Kristoffer. “Molecular basis for galectin-ligand interactions : Design, synthesis and analysis of ligands.” 2018. Doctoral Dissertation, University of Lund. Accessed April 15, 2021. https://lup.lub.lu.se/record/777b2fa7-2293-453b-9771-0f0ab6f6a6d2 ; https://portal.research.lu.se/ws/files/38414625/Thesis.pdf.

MLA Handbook (7^th Edition):

Peterson, Kristoffer. “Molecular basis for galectin-ligand interactions : Design, synthesis and analysis of ligands.” 2018. Web. 15 Apr 2021.

Vancouver:

Peterson K. Molecular basis for galectin-ligand interactions : Design, synthesis and analysis of ligands. [Internet] [Doctoral dissertation]. University of Lund; 2018. [cited 2021 Apr 15]. Available from: https://lup.lub.lu.se/record/777b2fa7-2293-453b-9771-0f0ab6f6a6d2 ; https://portal.research.lu.se/ws/files/38414625/Thesis.pdf.

Council of Science Editors:

Peterson K. Molecular basis for galectin-ligand interactions : Design, synthesis and analysis of ligands. [Doctoral Dissertation]. University of Lund; 2018. Available from: https://lup.lub.lu.se/record/777b2fa7-2293-453b-9771-0f0ab6f6a6d2 ; https://portal.research.lu.se/ws/files/38414625/Thesis.pdf

26. Juliana Alves dos Santos. Síntese e avaliação biológica de análogos de nucleosídeos e triazóis contendo açúcares.

Degree: 2011, Universidade Federal de Juiz de Fora

URL: http://www.bdtd.ufjf.br/tde_busca/arquivo.php?codArquivo=1105

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A presente dissertação, intitulada Síntese e avaliação biológica de análogos de nucleosídeos e triazóis contendo açúcares encontra-se dividida em duas partes que descrevem a síntese… (more)

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A presente dissertação, intitulada Síntese e avaliação biológica de análogos de nucleosídeos e triazóis contendo açúcares encontra-se dividida em duas partes que descrevem a síntese de moléculas pertencentes a dois grupos de heterociclos de grande valor biológico. A primeira parte trata da tentativa de síntese de um novo análogo do nucleosídeo natural 5‟-metil-tioadenosina (MTA). Uma vez que análogos nucleosídicos são amplamente utilizados na medicina e, em especial, análogos sintéticos da MTA são descritos como potenciais inibidores do ciclo de parasitas, propôs-se a obtenção do composto 9-(6‟-metiltio-β-D-psicofuranosil)-adenina 12 a partir da D-frutose, através de uma síntese linear em 11 etapas. O composto almejado difere de seu análogo natural por possuir um grupo hidroximetileno na posição 1‟ da parte ribosídica. OHOHOH3CSNNNNNH2OHOHOH3CSOHNNNNNH212MTA A segunda parte descreve a síntese de triazóis contendo açúcares, que são estruturas resultantes da conjugação de derivados de carboidratos e anéis triazólicos. Estes glicoconjugados têm se destacado na literatura por apresentarem uma vasta classe de atividade biológica tais como antiviral, antitumoral, anti-tripanossômica e como inibidores de α-glicosidases. Para síntese dos triazóis contendo açúcares (compostos 15-19), utilizou-se uma reação do tipo click chemistry que é uma cicloadição 1,3-dipolar do alcino terminal 14 com diferentes derivados de azida (a-e). 14OOOOOOCOOHabcdeN3N3N3N3N3OHOOOOOONNNR15-19R=COOH1516171819

This work, entitled Synthesis and biological evaluation of derivatives of nucleosides and triazoles linked to sugars is divided into two parts that describe the synthesis of molecules belonging to two groups of heterocycles of great biological value. The first part shows the attempted synthesis of a novel nucleoside analogue natural 5‟-methyl-tioadenosine (MTA). Since nucleoside analogues are widely used in medicine and in particular synthetic analogues are described as potential inhibitors of the cycle of parasites, proposed to obtain the compound 9-(6‟-methylthio-β-psicofuranosil)-adenine 12, through a synthesis of 11 linear steps from D-fructose. The desired compound differs from its natural analogue for possessing a hydroxymethylene group at position 1‟ on the part riboside. OH OH O H3CS N N N N NH2 OH OH O H3CS OH N N N N NH2 12 MTA The second part describes the synthesis of triazoles linked to sugar, which structures are resulting from the combination of carbohydrate derivatives and triazoles rings. These glycoconjugates have been highlighted in the literature by presenting a broad class of biological activity as antiviral, anticancer, anti-tripanosomiasis as well as α-glucosidase inhibitors. For the synthesis of triazoles linked sugar desired compounds (15-19) was used for a reaction of the click chemistry which is a 1,3-dipolar cycloaddition of terminal alkyne 14 with various derivatives of azide (a-e). 14 O O O O O O C O OH a b c d e N3 N3 N3 N3 N3 OH O O O O O O N N N R 15-19…

Advisors/Committee Members: Mauro Vieira de Almeida, Ricardo José Alves, Adilson David da Silva.

Subjects/Keywords: QUIMICA ORGANICA; 5‟; -metil-tioadenosina (MTA); Nucleosídeos; Triazóis contendo açúcares; Cicloadição 1,3-dipolar; 5‟; -methyl-tioadenosine (MTA); Nucleosides; Triazoles linked to sugar; 1,3-dipolar cycloaddition

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APA · Chicago · MLA · Vancouver · CSE | Export to Zotero / EndNote / Reference Manager

APA (6^th Edition):

Santos, J. A. d. (2011). Síntese e avaliação biológica de análogos de nucleosídeos e triazóis contendo açúcares. (Thesis). Universidade Federal de Juiz de Fora. Retrieved from http://www.bdtd.ufjf.br/tde_busca/arquivo.php?codArquivo=1105

Note: this citation may be lacking information needed for this citation format:
Not specified: Masters Thesis or Doctoral Dissertation

Chicago Manual of Style (16^th Edition):

Santos, Juliana Alves dos. “Síntese e avaliação biológica de análogos de nucleosídeos e triazóis contendo açúcares.” 2011. Thesis, Universidade Federal de Juiz de Fora. Accessed April 15, 2021. http://www.bdtd.ufjf.br/tde_busca/arquivo.php?codArquivo=1105.

Note: this citation may be lacking information needed for this citation format:
Not specified: Masters Thesis or Doctoral Dissertation

MLA Handbook (7^th Edition):

Santos, Juliana Alves dos. “Síntese e avaliação biológica de análogos de nucleosídeos e triazóis contendo açúcares.” 2011. Web. 15 Apr 2021.

Vancouver:

Santos JAd. Síntese e avaliação biológica de análogos de nucleosídeos e triazóis contendo açúcares. [Internet] [Thesis]. Universidade Federal de Juiz de Fora; 2011. [cited 2021 Apr 15]. Available from: http://www.bdtd.ufjf.br/tde_busca/arquivo.php?codArquivo=1105.

Note: this citation may be lacking information needed for this citation format:
Not specified: Masters Thesis or Doctoral Dissertation

Council of Science Editors:

Santos JAd. Síntese e avaliação biológica de análogos de nucleosídeos e triazóis contendo açúcares. [Thesis]. Universidade Federal de Juiz de Fora; 2011. Available from: http://www.bdtd.ufjf.br/tde_busca/arquivo.php?codArquivo=1105

Note: this citation may be lacking information needed for this citation format:
Not specified: Masters Thesis or Doctoral Dissertation

Pontifical Catholic University of Rio de Janeiro

27. [No author]. [pt] EMPREGO DA REAÇÃO DE CICLOADIÇÃO 1,3-DIPOLAR CATALISADA POR COBRE PARA A OBTENÇÃO DE NOVOS 1,2,3-TRIAZÓIS COM AÇÃO ANTICÂNCER EM LINHAGENS DE GLIOBLASTOMA E ANTILEISHMANIAL IN VITRO.

Degree: 2020, Pontifical Catholic University of Rio de Janeiro

URL: http://www.maxwell.vrac.puc-rio.br/Busca_etds.php?strSecao=resultado&nrSeq=47735

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[pt] Diante da importância terapêutica dos 1,2,3-triazóis e da versatilidade da reação de cicloadição 1,3-dipolar de Huisgen catalisada por cobre (reação CuAAC), o presente trabalho… (more)

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[pt] Diante da importância terapêutica dos 1,2,3-triazóis e da versatilidade da reação de cicloadição 1,3-dipolar de Huisgen catalisada por cobre (reação CuAAC), o presente trabalho propõe a síntese de novos 1,2,3-triazóis-1,4-dissubstituídos abordando-se o conceito de hibridização molecular que associa ao núcleo triazólico outros grupos farmacofóricos privilegiados. Os compostos sintetizados foram divididos em duas séries e avaliados quanto ao potencial anticâncer, antileishmanial e distúrbios do sistema do nervoso central. Para obtenção da primeira série de triazóis utilizou-se como precursores aril azidas preparadas a partir de anilinas e éter propargílicos obtidos a partir de fenóis. A etapa chave da reação de CuAAC levou a obtenção dos 1,2,3-triazóis-1,4-dissubstituídos com rendimentos entre 50 e 85 porcento. Os compostos obtidos foram avaliados em diferentes linhagens celulares de glioblastoma (GBM, U87), incluindo linhagens celulares humanas altamente resistentes como a GBM02, GBM95, onde os compostos 2,2- (4,4-((1,3-phenilenebis(oxi))bis(methileno))bis(1H-1,2,3-triazol-4,1diyl))dibenzaldeído e (E)-4-metil-N-(2-(4-(fenoximetil)-1H-1,2,3triazolil)benzilideno)benzenosulfonohidrazida foram os mais ativos, com IC50 de 28,7 e 30,3 uM, respectivamente. Também foram avaliados nas linhagens de câncer de pulmão e próstata (A549, 22Rv1), entretanto, os compostos analisados não apresentaram atividade frente a estas linhagens celulares. Para a síntese da segunda série de compostos híbridos, tais quais os a-hidroxi-1,2,3-triazóis e benzocromenostriazóis, utilizou-se como materiais de partida aril azidas, preparadas através de ácidos aril borônicos e álcoois propargílicos, preparados a partir de benzaldeídos comerciais. A reação CuAAC na presença de metóxido de sódio levou a obtenção dos novos a-hidroxi-1,2,3-triazóis com rendimentos entre 35 e 75 porcento. A partir dos a-hidroxi-1,2,3-triazóis obtidos, realizou-se a reação de ativação C-H catalisada por paládio para obtenção benzocromenos-triazóis com rendimentos entre 35 e 40 porcento. Esses compostos foram avaliados como inibidores do transportador de glicina (Gly T1), transportadores relacionados a distúrbios neurológicos, e o composto (2-bromofenil)(1-(4-bromofenil)-1H-1,2,3-triazol-4-il)metanol apresentou 42porcento de inibição e IC50 de 13 uM, sendo este o melhor resultado de toda a série. Os compostos obtidos foram avaliados quanto a atividade antileishmanial (L. amazonenses), sendo que os compostos 2,2-(4,4-((1,3- phenilenebis(oxi))bis(methileno))bis(1H-1,2,3-triazol-4,1diyl)) dibenzaldeído e (E)-4-metil-N-(2-(4-(fenoximetil)-1H-1,2,3triazolil)benzilideno) benzenosulfonohidrazida apresentaram os melhores resultados, com IC50 de 8,85 e 8,81 uM, respectivamente. Todos os compostos sintetizados foram caracterizados por técnicas de espectroscopia de ressonância magnética nuclear (RMN), infravermelho (IV) e espectrometria de massas (CG-MS).

[en] In view of the therapeutic importance of 1,2,3-triazoles and the versatility of the copper-catalyzed Huisgen 1,3-dipolar…

Advisors/Committee Members: CAMILLA DJENNE BUARQUE MULLER.

Subjects/Keywords: [pt] REACOES DE ACOPLAMENTO; [en] COUPLING REACTIONS; [pt] 123 TRIAZOL; [en] 123 TRIAZOLE; [pt] CICLOADICAO 13-DIPOLAR; [en] 13-DIPOLAR CYCLOADDITION; [pt] CUAAC; [en] CUAAC

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APA · Chicago · MLA · Vancouver · CSE | Export to Zotero / EndNote / Reference Manager

APA (6^th Edition):

author], [. (2020). [pt] EMPREGO DA REAÇÃO DE CICLOADIÇÃO 1,3-DIPOLAR CATALISADA POR COBRE PARA A OBTENÇÃO DE NOVOS 1,2,3-TRIAZÓIS COM AÇÃO ANTICÂNCER EM LINHAGENS DE GLIOBLASTOMA E ANTILEISHMANIAL IN VITRO. (Thesis). Pontifical Catholic University of Rio de Janeiro. Retrieved from http://www.maxwell.vrac.puc-rio.br/Busca_etds.php?strSecao=resultado&nrSeq=47735

Note: this citation may be lacking information needed for this citation format:
Not specified: Masters Thesis or Doctoral Dissertation

Chicago Manual of Style (16^th Edition):

author], [No. “[pt] EMPREGO DA REAÇÃO DE CICLOADIÇÃO 1,3-DIPOLAR CATALISADA POR COBRE PARA A OBTENÇÃO DE NOVOS 1,2,3-TRIAZÓIS COM AÇÃO ANTICÂNCER EM LINHAGENS DE GLIOBLASTOMA E ANTILEISHMANIAL IN VITRO.” 2020. Thesis, Pontifical Catholic University of Rio de Janeiro. Accessed April 15, 2021. http://www.maxwell.vrac.puc-rio.br/Busca_etds.php?strSecao=resultado&nrSeq=47735.

Note: this citation may be lacking information needed for this citation format:
Not specified: Masters Thesis or Doctoral Dissertation

MLA Handbook (7^th Edition):

author], [No. “[pt] EMPREGO DA REAÇÃO DE CICLOADIÇÃO 1,3-DIPOLAR CATALISADA POR COBRE PARA A OBTENÇÃO DE NOVOS 1,2,3-TRIAZÓIS COM AÇÃO ANTICÂNCER EM LINHAGENS DE GLIOBLASTOMA E ANTILEISHMANIAL IN VITRO.” 2020. Web. 15 Apr 2021.

Vancouver:

author] [. [pt] EMPREGO DA REAÇÃO DE CICLOADIÇÃO 1,3-DIPOLAR CATALISADA POR COBRE PARA A OBTENÇÃO DE NOVOS 1,2,3-TRIAZÓIS COM AÇÃO ANTICÂNCER EM LINHAGENS DE GLIOBLASTOMA E ANTILEISHMANIAL IN VITRO. [Internet] [Thesis]. Pontifical Catholic University of Rio de Janeiro; 2020. [cited 2021 Apr 15]. Available from: http://www.maxwell.vrac.puc-rio.br/Busca_etds.php?strSecao=resultado&nrSeq=47735.

Note: this citation may be lacking information needed for this citation format:
Not specified: Masters Thesis or Doctoral Dissertation

Council of Science Editors:

author] [. [pt] EMPREGO DA REAÇÃO DE CICLOADIÇÃO 1,3-DIPOLAR CATALISADA POR COBRE PARA A OBTENÇÃO DE NOVOS 1,2,3-TRIAZÓIS COM AÇÃO ANTICÂNCER EM LINHAGENS DE GLIOBLASTOMA E ANTILEISHMANIAL IN VITRO. [Thesis]. Pontifical Catholic University of Rio de Janeiro; 2020. Available from: http://www.maxwell.vrac.puc-rio.br/Busca_etds.php?strSecao=resultado&nrSeq=47735

Note: this citation may be lacking information needed for this citation format:
Not specified: Masters Thesis or Doctoral Dissertation

28. Lobo, Marcio Marçal. Síntese regiosseletiva de Dideoxinucleosídeos e 3(5)-Trifluormetil-1H-pirazóis de interesse farmacológico.

Degree: 2015, Universidade Federal de Santa Maria; Programa de Pós-Graduação em Química; UFSM; BR; Química

URL: http://repositorio.ufsm.br/handle/1/4276

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Conselho Nacional de Desenvolvimento Científico e Tecnológico

This work reports the synthesis of a series of 29 new 1-(3-aryl-4,5-dihydroisoxazol-5-yl)methyl-4-trihalomethylpyrimidin-2(1H)-ones which have high pharmacological interest, since… (more)

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Conselho Nacional de Desenvolvimento Científico e Tecnológico

This work reports the synthesis of a series of 29 new 1-(3-aryl-4,5-dihydroisoxazol-5-yl)methyl-4-trihalomethylpyrimidin-2(1H)-ones which have high pharmacological interest, since they are similar to natural and synthetic nucleosides. These compounds were obtained from 1,3-dippolar cycloaddition reaction between the 1-allyl-(6-aryl)-4-trihalomethylpyrimidin-2(1H)-ones and different benzonitrile oxides, obtained from the selected oximes of general formula ArCH=NOH (where Ar = Ph, 4-FC6H4, 2-MeC6H4, 4-MeC6H4, 2-MeOC6H4, 4-MeOC6H4, styryl, 2-OHC6H4 e 4-OHC6H4). The reaction conditions employed were highly regioselective, because it was observed the formation of only 3,5-substituted isomer by both NMR spectral analysis and X-ray diffractometry. The compounds were obtained in good yields (58 99%) and were purified from recrystallization or by column chromatography on silica gel. Some the obtained compounds showed antineoplastic activity in vitro against different tumor cell lines. Additionally, three new N3-substituted pyrimidinic dideoxynucleoside analogues were prepared, which were obtained in good yields (88 97%) from the reaction of N-allyl-2-methylthiopyrimidin-4(3H)-one and some of the benzonitrile oxides mentioned above. The reactions for the formation of N3-substituted nucleoside still require optimization. This thesis also described the regiochemisty controled synthesis of two series of pyrazoles, named 5(3)-aryl-3(5)-trifluoromethyl-(1H-pyrazol-1-yl)benzenesulfonamides, structural analogues of Celecoxib (14 examples), where aryl = Ph, 4-FC6H4, 4-MeC6H4, 4-MeOC6H4, 4-ClC6H4, 4-BrC6H4, furan-2-yl, from the cyclocondensation reaction between 4-aryl-1,1,1-trifluoromethyl-4-methoxy-3-buten-2-ones and 4-hydrazinobenzenosulfonamide hydrochloride. The isolation of either isomer depended on the initial pH medium, where the alkaline pH favored the isolation of the 1,5-substituted isomer at yields of 73 99% and the reaction conducted in acid pH favored the isolation of the 1,3-substituted isomer, with yields of 77 94%. This study also allowed the isolation and spectroscopic characterization of a novel series of 3-aryl(heteroaryl)-5-hydroxy-5-trifluoromethyl-(1H-pyrazol-1-yl)benzenesulfonamides (7 examples) in yields of 75 97% with interesting anti-inflammatory and antinociceptive activities in vivo.

Esta tese apresenta a síntese de uma série de 29 moléculas inéditas de 1-(3-aril-4,5-diidroisoxazol-5-il)metil-4-trialometilpirimidin-2(1H)-onas que possuem alto interesse farmacológico, visto que são análogos a nucleosídeos naturais e sintéticos. Esses compostos foram obtidos a partir de reação de cicloadição 1,3-dipolar entre as 1-alil-(6-aril)-4-trialometilpirimidin-2(1H)-onas e diferentes óxidos de benzonitrila, obtidos a partir das oximas selecionadas, de fórmula geral ArCH=NOH (onde Ar = Ph, 4-FC6H4, 2-MeC6H4, 4-MeC6H4, 2-MeOC6H4, 4-MeOC6H4, Estiril, 2-OHC6H4 e 4-OHC6H4). As condições reacionais empregadas mostraram-se altamente regiosseletivas, uma vez…

Advisors/Committee Members: Zanatta, Nilo, Morel, Ademir Farias, Frizzo, Clarissa Piccinin, Fantinel, Leonardo, Amaral, Simone Schneider.

Subjects/Keywords: Cicloadição 1,3-dipolar; Isoxazol; Pirazol; Nucleosídeo; Celecoxib; Regiosseletividade; Trifluormetil-1H-pirazol; 1,3-dipolar cycloaddition; Isoxazole; Pyrazole; Nucleoside; Celecoxib; Regioselectivity; Trifluoromethyl-1H-pyrazole; CNPQ::CIENCIAS EXATAS E DA TERRA::QUIMICA

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APA (6^th Edition):

Lobo, M. M. (2015). Síntese regiosseletiva de Dideoxinucleosídeos e 3(5)-Trifluormetil-1H-pirazóis de interesse farmacológico. (Doctoral Dissertation). Universidade Federal de Santa Maria; Programa de Pós-Graduação em Química; UFSM; BR; Química. Retrieved from http://repositorio.ufsm.br/handle/1/4276

Chicago Manual of Style (16^th Edition):

Lobo, Marcio Marçal. “Síntese regiosseletiva de Dideoxinucleosídeos e 3(5)-Trifluormetil-1H-pirazóis de interesse farmacológico.” 2015. Doctoral Dissertation, Universidade Federal de Santa Maria; Programa de Pós-Graduação em Química; UFSM; BR; Química. Accessed April 15, 2021. http://repositorio.ufsm.br/handle/1/4276.

MLA Handbook (7^th Edition):

Lobo, Marcio Marçal. “Síntese regiosseletiva de Dideoxinucleosídeos e 3(5)-Trifluormetil-1H-pirazóis de interesse farmacológico.” 2015. Web. 15 Apr 2021.

Vancouver:

Lobo MM. Síntese regiosseletiva de Dideoxinucleosídeos e 3(5)-Trifluormetil-1H-pirazóis de interesse farmacológico. [Internet] [Doctoral dissertation]. Universidade Federal de Santa Maria; Programa de Pós-Graduação em Química; UFSM; BR; Química; 2015. [cited 2021 Apr 15]. Available from: http://repositorio.ufsm.br/handle/1/4276.

Council of Science Editors:

Lobo MM. Síntese regiosseletiva de Dideoxinucleosídeos e 3(5)-Trifluormetil-1H-pirazóis de interesse farmacológico. [Doctoral Dissertation]. Universidade Federal de Santa Maria; Programa de Pós-Graduação em Química; UFSM; BR; Química; 2015. Available from: http://repositorio.ufsm.br/handle/1/4276

29. Figueirôa, Juliana Andreza. Síntese e caracterização de novos compostos mesoiônicos e derivados dos sistemas 1,3-tiazólio-5-tiolato e 1,3-diazólio-5-tiolato.

Degree: 2012, Universidade Federal da Paraíba; Programa de Pós-Graduação em Química; UFPB; BR; Química

URL: https://repositorio.ufpb.br/jspui/handle/tede/7063

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Financiadora de Estudos e Projetos - Finep

Mesoionic compounds are notable heterocyclic for having the most diverse biological properties, physical and chemical properties. Are defined as flat and non-aromatic heterocyclic Betaines stabilized by electron delocalization. Through an in situ cycloaddition/cicloreversion 1,3-dipolar were obtained two mesoionic, MI-1.1 and MI-1.2 through of the interconversion system 1,3-oxazólio-5-olato (Munchnonas) for 1,3-tiazólio-5-tiolato. A nucleophilic substitution reaction with excess methyl iodide, CH3I, promoted the first modification to the mesoionic system were changed of free base to iodates salts, S-methylated forming derivatives mesoionic, MI-2.1 e MI-2.2. These underwent a cyclodehydration reaction in the presence of acetic anhydride yielding two mesoionic system 1,3-diazolium-5-thiolate, MI-3.1 and MI-3.2, which in turn were alkylated again and originated two derived in the form of iodates salts S-methylated, MI-4.1 and MI-4.2. As the mesoionic and its derivatives: MI-2.1, MI-2.2, MI-3.1, MI-3.2, MI-4.1 and MI-4.2 and unpublished literature. Their structures were elucidated by spectroscopic techniques for RMN 1H and 13C and infrared light through a comparative analysis with existing structures.

Os compostos mesoiônicos são heterocíclicos notáveis por apresentar as mais diversas propriedades biológicas, físicas e químicas. São definidos como betaínas heterocíclicas planas e não aromáticas estabilizadas por deslocalização de elétrons. Através de uma reação in situ de cicloadição/cicloreversão 1,3-dipolar obtiveram-se dois mesoiônicos, MI-1.1 e MI-1.2, através da interconversão do sistema 1,3-oxazólio-5-olato (Munchnonas) para 1,3-tiazólio-5-tiolato. Uma reação de substituição nucleofílica com excesso de iodeto de metila, CH3I, promoveu a primeira modificação no sistema mesoiônico sendo transformados de base livre para sais iodatos S-metilados formando os derivados mesoiônicos, MI-2.1 e MI-2.2. Estes sofreram uma reação de ciclodesidratação na presença de anidrido acético obtendo-se dois mesoiônicos do sistema 1,3-diazólio-5-tiolato, MI-3.1 e MI-3.2, que por sua vez foram alquilados novamente e originaram dois derivados em forma de sais iodatos S-metilados, MI-4.1 e MI-4.2. Sendo os mesoiônicos e seus derivados: MI-2.1, MI-2.2, MI-3.1, MI-3.2, MI-4.1 e MI-4.2 inéditos na literatura. Suas estruturas foram elucidadas por meio de técnicas espectroscópicas de RMN 1H e 13C e infravermelho através de uma análise comparativa com estruturas já existentes.

Advisors/Committee Members: Lira, Bruno Freitas, Athayde Filho, Petrônio Filqueiras de.

Subjects/Keywords: Compostos mesoiônicos; Reações de cicloadição/reversão 1,3-dipolar; Técnicas espectroscópias; Mesoionic Compounds; Cycloaddition Reactions / Cycloreversion 1,3-dipolar; Spectroscopic techniques; CIENCIAS EXATAS E DA TERRA::QUIMICA

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APA · Chicago · MLA · Vancouver · CSE | Export to Zotero / EndNote / Reference Manager

APA (6^th Edition):

Figueirôa, J. A. (2012). Síntese e caracterização de novos compostos mesoiônicos e derivados dos sistemas 1,3-tiazólio-5-tiolato e 1,3-diazólio-5-tiolato. (Masters Thesis). Universidade Federal da Paraíba; Programa de Pós-Graduação em Química; UFPB; BR; Química. Retrieved from https://repositorio.ufpb.br/jspui/handle/tede/7063

Chicago Manual of Style (16^th Edition):

Figueirôa, Juliana Andreza. “Síntese e caracterização de novos compostos mesoiônicos e derivados dos sistemas 1,3-tiazólio-5-tiolato e 1,3-diazólio-5-tiolato.” 2012. Masters Thesis, Universidade Federal da Paraíba; Programa de Pós-Graduação em Química; UFPB; BR; Química. Accessed April 15, 2021. https://repositorio.ufpb.br/jspui/handle/tede/7063.

MLA Handbook (7^th Edition):

Figueirôa, Juliana Andreza. “Síntese e caracterização de novos compostos mesoiônicos e derivados dos sistemas 1,3-tiazólio-5-tiolato e 1,3-diazólio-5-tiolato.” 2012. Web. 15 Apr 2021.

Vancouver:

Figueirôa JA. Síntese e caracterização de novos compostos mesoiônicos e derivados dos sistemas 1,3-tiazólio-5-tiolato e 1,3-diazólio-5-tiolato. [Internet] [Masters thesis]. Universidade Federal da Paraíba; Programa de Pós-Graduação em Química; UFPB; BR; Química; 2012. [cited 2021 Apr 15]. Available from: https://repositorio.ufpb.br/jspui/handle/tede/7063.

Council of Science Editors:

Figueirôa JA. Síntese e caracterização de novos compostos mesoiônicos e derivados dos sistemas 1,3-tiazólio-5-tiolato e 1,3-diazólio-5-tiolato. [Masters Thesis]. Universidade Federal da Paraíba; Programa de Pós-Graduação em Química; UFPB; BR; Química; 2012. Available from: https://repositorio.ufpb.br/jspui/handle/tede/7063

30. Treesa, P M. Novel Cycloaddition Reactions of o-Quinone Methides and Related Chemistry.

Degree: 2001, Cochin University of Science and Technology

URL: http://dyuthi.cusat.ac.in/purl/2969

Subjects/Keywords: o-Quinone Methides; Dipolar Cycloaddition reactions; Chemistry

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APA · Chicago · MLA · Vancouver · CSE | Export to Zotero / EndNote / Reference Manager

APA (6^th Edition):

Treesa, P. M. (2001). Novel Cycloaddition Reactions of o-Quinone Methides and Related Chemistry. (Thesis). Cochin University of Science and Technology. Retrieved from http://dyuthi.cusat.ac.in/purl/2969

Note: this citation may be lacking information needed for this citation format:
Not specified: Masters Thesis or Doctoral Dissertation

Chicago Manual of Style (16^th Edition):

Treesa, P M. “Novel Cycloaddition Reactions of o-Quinone Methides and Related Chemistry.” 2001. Thesis, Cochin University of Science and Technology. Accessed April 15, 2021. http://dyuthi.cusat.ac.in/purl/2969.

Note: this citation may be lacking information needed for this citation format:
Not specified: Masters Thesis or Doctoral Dissertation

MLA Handbook (7^th Edition):

Treesa, P M. “Novel Cycloaddition Reactions of o-Quinone Methides and Related Chemistry.” 2001. Web. 15 Apr 2021.

Vancouver:

Treesa PM. Novel Cycloaddition Reactions of o-Quinone Methides and Related Chemistry. [Internet] [Thesis]. Cochin University of Science and Technology; 2001. [cited 2021 Apr 15]. Available from: http://dyuthi.cusat.ac.in/purl/2969.

Note: this citation may be lacking information needed for this citation format:
Not specified: Masters Thesis or Doctoral Dissertation

Council of Science Editors:

Treesa PM. Novel Cycloaddition Reactions of o-Quinone Methides and Related Chemistry. [Thesis]. Cochin University of Science and Technology; 2001. Available from: http://dyuthi.cusat.ac.in/purl/2969

Note: this citation may be lacking information needed for this citation format:
Not specified: Masters Thesis or Doctoral Dissertation

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