subject:(Chemistry Organic)

Iowa State University

1. Drochner, Dana Lynn. Rational design and characterization of electron-deficient heterocycles for organic photovoltaic materials.

Degree: 2015, Iowa State University

URL: https://lib.dr.iastate.edu/etd/14793

► This research explores the synthesis and evaluation of new building blocks and polymers for organic photovoltaic materials. Through the development of new synthetic routes and… (more)

Subjects/Keywords: Organic Chemistry; Chemistry; Organic Chemistry

Record Details Similar Records Cite « Share

❌

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

APA (6^th Edition):

Drochner, D. L. (2015). Rational design and characterization of electron-deficient heterocycles for organic photovoltaic materials. (Thesis). Iowa State University. Retrieved from https://lib.dr.iastate.edu/etd/14793

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):

Drochner, Dana Lynn. “Rational design and characterization of electron-deficient heterocycles for organic photovoltaic materials.” 2015. Thesis, Iowa State University. Accessed February 27, 2021. https://lib.dr.iastate.edu/etd/14793.

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

MLA Handbook (7^th Edition):

Drochner, Dana Lynn. “Rational design and characterization of electron-deficient heterocycles for organic photovoltaic materials.” 2015. Web. 27 Feb 2021.

Vancouver:

Drochner DL. Rational design and characterization of electron-deficient heterocycles for organic photovoltaic materials. [Internet] [Thesis]. Iowa State University; 2015. [cited 2021 Feb 27]. Available from: https://lib.dr.iastate.edu/etd/14793.

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

Council of Science Editors:

Drochner DL. Rational design and characterization of electron-deficient heterocycles for organic photovoltaic materials. [Thesis]. Iowa State University; 2015. Available from: https://lib.dr.iastate.edu/etd/14793

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

2. Jayasekara, Himali Devika. Photochemical Elimination Reactions that Proceed via Triplet Excited State Electrocyclic Ring Closures.

Degree: 2014, Marquette University

URL: https://epublications.marquette.edu/theses_open/247

► Cage compounds have become an important tool for the study of biological processes. The research focuses on new cage compounds that can unmask functional groups… (more)

▼ Cage compounds have become an important tool for the study of biological processes. The research focuses on new cage compounds that can unmask functional groups present in biologically important molecules such as proteins, peptides, and oligonucleosides. The project focuses on certain functional groups that are often difficult to release photochemically. These are the thiolate groups present in cysteine residues of proteins and peptides. Thiolate groups are fairly basic leaving groups, unlike the more labile groups such as the carboxylates that are present in proteins and peptides, or the phosphate groups present in nucleosides. The research takes advantage of the ability of zwitterionic intermediates to release basic leaving groups such as the thiolates. The zwitterionic intermediates are generated photochemically by electrocyclic ring closure of aromatic carboxamides that has the chromophore attached to the amide nitrogen. Most importantly, the research utilizes a chromophore that absorbs visible light, so as to minimize the damaging effects that short-wavelength light has on tissue and cells. The research recognizes that triplet energy transfer from triplet excited state of the chromophore to the aromatic ring system attached to carboxamide carbonyl group must be exothermic in order for the electrocyclic ring closure to occur. For a thioxanthone chromophore (ET = 64 kcal mol-1), the aromatic ring system is a naphthothiophene ring system (ET = 62 kcal mol-1). The energy transfer would therefore be exothermic. This cage compound was synthesized with a 3-chloro leaving group. It undergoes photochemical electrocyclic ring closure and chloride expulsion in 50% yield after 1.5 h photolysis. The reaction qualitatively appears to be efficient. In comparison, a 5-benzoylthiophene aromatic ring system with 3-chloro group undergoes the same photoreaction in very low yields over 72 h, even though the triplet energy transfer is exothermic. In this case the photoproduct effectively competes for the incident light with the reactant. The research shows that the naphthothiophene ring system is a viable solution to the triplet energy transfer problem. It also points to a need to improve the solubility of the cage compound by incorporating one or more carboxylate groups into the naphthothiophene ring or the thioxanthone ring. Advisors/Committee Members: Steinmetz, Mark G., Donaldson, William A., Timerghazin, Qadir K..

Subjects/Keywords: Organic chemistry; Chemistry; Organic Chemistry

Record Details Similar Records Cite « Share

❌

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

APA (6^th Edition):

Jayasekara, H. D. (2014). Photochemical Elimination Reactions that Proceed via Triplet Excited State Electrocyclic Ring Closures. (Thesis). Marquette University. Retrieved from https://epublications.marquette.edu/theses_open/247

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):

Jayasekara, Himali Devika. “Photochemical Elimination Reactions that Proceed via Triplet Excited State Electrocyclic Ring Closures.” 2014. Thesis, Marquette University. Accessed February 27, 2021. https://epublications.marquette.edu/theses_open/247.

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

MLA Handbook (7^th Edition):

Jayasekara, Himali Devika. “Photochemical Elimination Reactions that Proceed via Triplet Excited State Electrocyclic Ring Closures.” 2014. Web. 27 Feb 2021.

Vancouver:

Jayasekara HD. Photochemical Elimination Reactions that Proceed via Triplet Excited State Electrocyclic Ring Closures. [Internet] [Thesis]. Marquette University; 2014. [cited 2021 Feb 27]. Available from: https://epublications.marquette.edu/theses_open/247.

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

Council of Science Editors:

Jayasekara HD. Photochemical Elimination Reactions that Proceed via Triplet Excited State Electrocyclic Ring Closures. [Thesis]. Marquette University; 2014. Available from: https://epublications.marquette.edu/theses_open/247

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

University of Helsinki

3. Raffaelli, Barbara. Synthesis of lignano-9,9'-lactones and rearrangement studies.

Degree: Department of Chemistry, Laboratory of Organic Chemistry, 2012, University of Helsinki

URL: http://hdl.handle.net/10138/37066

►

Lignans are found as naturally occurring compounds in plants, and also as metabolites in mammals. Due to their biological activity, lignans have attracted the interest… (more)

▼

Lignans are found as naturally occurring compounds in plants, and also as metabolites in mammals. Due to their biological activity, lignans have attracted the interest of scientists from different areas like food chemistry, synthetic chemistry, and clinical chemistry. The research is very active, as evident by the number of publications related to this subject that are published annually. The present work focuses on the chemistry of certain classes of lignan, namely lignano-9,9'-lactones and their rearranged products. The literature review is based on the synthesis of lignano-9,9'-lactones and 7'-OH-lignano-9,9'-lactones. Both racemic and asymmetric protocols appeared as from year 2000 have been extensively reviewed. In addition, the literature concerning the rearrangement reaction of 7'-OH-lignano-9,9'-lactones have been discussed. The experimental section presents the development of a stereoselective synthesis to obtain 7'-hydroxylignanolactones. Subsequently, the known rearrangement reactions affecting hydroxylignanolactones are discussed. The stereochemistry of certain lignanolactones is a core part of this work and the findings of this study allowed the revision of certain controversial data found in the literature. For the first time, the X-ray structures of 7'-OH-lignano-9,9'-lactones were obtained. In addition, the synthesis of possible lignan metabolites is also presented. A summary of the available 1H NMR data for selected (7'S)- and (7'R)-OH-lignano-9,9'-lactones and for various lignano-9,7'-lactone stereoisomers has been made available in the Appendix section.

Lignaanit ovat mielenkiintoinen ihmisen terveyteen vaikuttavien aineiden ryhmä, joita esiintyy luonnossa kasveissa, erityisesti hedelmissä ja vihanneksissa. Lignaaneihin kohdistuva tieteellinen mielenkiinto johtuu niiden moninaisista rakennevariaatioista, ja ennen kaikkea niiden monista biologisista vaikutuksista. Lignaanien perusrakenne koostuu kahdesta fenyylipropaaniyksiköstä, jotka ovat sitoutuneet toisiinsa C-C -sidoksella propaaniyksikköjen keskihiilien kautta. Rakenteellista monimuotoisuutta aiheuttavat muut C-C sidokset, hapetusasteen vaihtelut, ja sekä alifaattisiin että aromaattisiin hiiliatomeihin kiinnittyneet erilaiset substituentit. Kasvikunta käyttää lignaaneja sienten ja hyönteisten torjuntaan. Ajankohtaisempaa on lignaanien merkitys liittyen ihmisen terveyteen. Kirjallisuudessa on raportoitu syövän vastaisista, antioksidatiivisista, anti-inflammatorisista ja apoptoottisista vaikutuksista sekä virusten torjunnasta. Suurta mielenkiintoa ovat herättäneet ihmisistä löytyneet lignaanit, jotka ovat muodostuneet elimistön aineenvaihdunnan tuloksena ravinnon mukana nautituista kasvilignaanerista. Näillä uusilla enterolignaaneilla on havaittu suojaavaa vaikutusta moninaisia terveyden haittatiloja kohtaan, kuten eturauhas-, rinta-, suoli- ja muut syövät, sydän- ja verisuonitaudit, aivotaudit, menopaussioireet ja osteoporoosi. Enterolignaanien rakenne muistuttaa endogeenisen 17beta-estradiolihormonin rakennetta, ja enterolignaanien…

Subjects/Keywords: organic Chemistry; organic Chemistry

Record Details Similar Records Cite « Share

❌

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

APA (6^th Edition):

Raffaelli, B. (2012). Synthesis of lignano-9,9'-lactones and rearrangement studies. (Doctoral Dissertation). University of Helsinki. Retrieved from http://hdl.handle.net/10138/37066

Chicago Manual of Style (16^th Edition):

Raffaelli, Barbara. “Synthesis of lignano-9,9'-lactones and rearrangement studies.” 2012. Doctoral Dissertation, University of Helsinki. Accessed February 27, 2021. http://hdl.handle.net/10138/37066.

MLA Handbook (7^th Edition):

Raffaelli, Barbara. “Synthesis of lignano-9,9'-lactones and rearrangement studies.” 2012. Web. 27 Feb 2021.

Vancouver:

Raffaelli B. Synthesis of lignano-9,9'-lactones and rearrangement studies. [Internet] [Doctoral dissertation]. University of Helsinki; 2012. [cited 2021 Feb 27]. Available from: http://hdl.handle.net/10138/37066.

Council of Science Editors:

Raffaelli B. Synthesis of lignano-9,9'-lactones and rearrangement studies. [Doctoral Dissertation]. University of Helsinki; 2012. Available from: http://hdl.handle.net/10138/37066

McMaster University

4. Jeyakanthan, Ketharagowry. A STUDY OF THE EFFECTS INTRAMOLECULAR π-COMPLEXATION ON THE REACTIVITY OF TRANSIENT ARYL(3-BUTENYL)GERMYLENES.

Degree: MSc, 2014, McMaster University

URL: http://hdl.handle.net/11375/14137

►

Three novel 1-aryl-1-(3-butenyl)germacyclopent-3-enes (26a, 26b and 26c) were synthesized and their photochemistry in hexane solution was studied by steady state and laser flash photolysis… (more)

▼

Three novel 1-aryl-1-(3-butenyl)germacyclopent-3-enes (26a, 26b and 26c) were synthesized and their photochemistry in hexane solution was studied by steady state and laser flash photolysis (LFP) methods. Steady state photolysis of 1-(3-butenyl)-3,4-dimethyl-1-phenylgermacyclopent-3- ene (26a) was found to proceed cleanly to afford the corresponding germylene derived product along with 2,3-dimethyl-1,3-butadiene (DMB) in the presence of acetic acid, methanol and isoprene, suggesting that free (3-butenyl)phenylgermylene (GeBuPh) is the primary photochemically generated species. However, we were unable to detect the germylene by laser flash photolysis with this compound, due to rapid “self –quenching” of the germylene by the precursor. The direct detection of the germylene in solution by laser flash photolysis requires the use of a more strongly absorbing derivative. Indeed, 3-butenylphenylgermylene (GeBuPh) was successfully detected directly by laser flash photolysis of 1-(3-butenyl)-3-methyl-1,4-diphenylgermacyclopent-3-ene (26b) in hexane solution, where it exhibits a UV-Vis absorption band centered at λmax= 490 nm and decays with second order kinetics on the microsecond timescale. In the absence of reactive substrates the decay of GeBuPh is accompanied by the growth of a second transient absorption, assigned to Ge2Bu2Ph2 (34) λmax = 420 nm; the assignment is based on a comparison to the laser flash photolysis of 1,3-dimethyl-1,4- diphenylgermacyclopent-3-ene (26d). Rate constants have been determined for reaction iv of the germylene with selected germylene substrates in order to evaluate the effects of intramolecular π-complexation on its reactivity. The results indicate that GeBuPh exhibits similar reactivity to GeMePh under otherwise identical experimental conditions, and thus show no significant indication of intramolecular π-complexation. With this in mind we have synthesized and studied 1-(3-butenyl)-3-methyl-4- phenyl-1-[3,5-bis(trifluoromethyl)phenyl]germacyclopent-3-ene (26c), which was designed to produce a more strongly electrophilic Ge(II) center in the corresponding germylene. The germylene 46 is detectable as a weakly absorbing transient species with λmax = 490 nm by laser flash photolysis of 26c in hexane solution. Generation of germylene 46 in the presence of THF leads to the formation of the corresponding Lewis acid base complex 48 at λmax = 330 nm. The reactivity of germylene 46 with selected substrates such as AcOH, THF and isoprene has been examined and the results compared to analogous data for the parent germylene GeBuPh. The forward rate constant for germylene 46 with acetic acid is slightly higher than that for GeBuPh, and no evidence for intramolecular complexation with the remote C=C bond could be obtained.

Master of Science (MSc)

Advisors/Committee Members: J.Leigh, William, Vargas-Baca, Ignacio, Chemistry and Chemical Biology.

Subjects/Keywords: Organic Chemistry; Organic Chemistry

Record Details Similar Records Cite « Share

❌

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

APA (6^th Edition):

Jeyakanthan, K. (2014). A STUDY OF THE EFFECTS INTRAMOLECULAR π-COMPLEXATION ON THE REACTIVITY OF TRANSIENT ARYL(3-BUTENYL)GERMYLENES. (Masters Thesis). McMaster University. Retrieved from http://hdl.handle.net/11375/14137

Chicago Manual of Style (16^th Edition):

Jeyakanthan, Ketharagowry. “A STUDY OF THE EFFECTS INTRAMOLECULAR π-COMPLEXATION ON THE REACTIVITY OF TRANSIENT ARYL(3-BUTENYL)GERMYLENES.” 2014. Masters Thesis, McMaster University. Accessed February 27, 2021. http://hdl.handle.net/11375/14137.

MLA Handbook (7^th Edition):

Jeyakanthan, Ketharagowry. “A STUDY OF THE EFFECTS INTRAMOLECULAR π-COMPLEXATION ON THE REACTIVITY OF TRANSIENT ARYL(3-BUTENYL)GERMYLENES.” 2014. Web. 27 Feb 2021.

Vancouver:

Jeyakanthan K. A STUDY OF THE EFFECTS INTRAMOLECULAR π-COMPLEXATION ON THE REACTIVITY OF TRANSIENT ARYL(3-BUTENYL)GERMYLENES. [Internet] [Masters thesis]. McMaster University; 2014. [cited 2021 Feb 27]. Available from: http://hdl.handle.net/11375/14137.

Council of Science Editors:

Jeyakanthan K. A STUDY OF THE EFFECTS INTRAMOLECULAR π-COMPLEXATION ON THE REACTIVITY OF TRANSIENT ARYL(3-BUTENYL)GERMYLENES. [Masters Thesis]. McMaster University; 2014. Available from: http://hdl.handle.net/11375/14137

Iowa State University

5. Goswami, Pratik Pran. Development of light- and chemo-sensitive probes for biochemical methods.

Degree: 2015, Iowa State University

URL: https://lib.dr.iastate.edu/etd/14369

► Part I. Photocages, which are light cleavable protecting groups, are an important class of chemical tools that allow light to unmask bioactive substrates with precise… (more)

▼ Part I. Photocages, which are light cleavable protecting groups, are an important class of chemical tools that allow light to unmask bioactive substrates with precise spatiotemporal resolution in biological microenvironments. Due to their effectiveness in biological systems, it has become increasingly important to find logically designed photocages that can cleave under visible light and Near IR conditions, wavelengths with minimal phototoxicity and increased tissue penetration compared to ultraviolet light. The scope of this research is to both rationally design and synthesize a new class of photocage based on the BODIPY moiety, as well as to modify these photocages to absorb in region of the biological window (600-1000 nm), where tissues have maximal transparency. In chapter 1, photocages derived from meso-substituted BODIPY dyes were synthesized that release acetic acid when irradiated with green wavelengths (>500 nm). The structures of the photocages were derived by computationally searching for carbocations with low-energy diradical states as a possible indicator of nearby productive conical intersections. These photocages were found to have superior optical properties than the popular o-nitrobenzyl systems, which make them promising alternatives. The utility of these photocages in living cells was successfully demonstrated by our collaborators (Prof. Emily Smith and Aleem Syed) in cultured S2 cells. In Chapter 2, Knoevenagel type reactions were used to extend the π electron conjugation of the aromatic rings of the BODIPY photocages. This extended conjugation of these BODIPY photocages resulted in a bathochromic shift in absorbance towards red light (>600 nm) and allows cleavage using wavelengths in the biological window. Part II. Self-immolative linkers can be used to trigger the release of an important cargo molecule like a drug or a biomolecule. A variety of trigger stimulants including light, chemo and enzyme are known in literature. However, there is a need for new linker units which would have fast and controllable kinetics of cargo release. During my research, I identified improved self-immolative linker units based on aryl phthalate esters with a modular design, which can tolerate a range of different trigger and cargo units. In Chapter 3, new types of self-immolative linkers based on the phenyl hydrogen phthalate system were synthesized. The fast kinetic rate for the hydrolysis of phenyl hydrogen phthalate system and the resulting benign byproducts promise a robust self-immolative linker system that can be used in biological systems. The linker system was shown to release phenol based cargo molecules including phenol and coumarin dyes upon cleavage by a fluoride sensitive trigger. This type of linker can also be potentially used as an efficient fluoride sensor. In Chapter 4, the scope of self-immolative linkers based on phenyl hydrogen phthalate system was extended. Light and peroxide sensitive triggers were incorporated into the linker system. Coumarin based cargo molecules were used as reporter…

Subjects/Keywords: Organic Chemistry; Organic Chemistry

Record Details Similar Records Cite « Share

❌

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

APA (6^th Edition):

Goswami, P. P. (2015). Development of light- and chemo-sensitive probes for biochemical methods. (Thesis). Iowa State University. Retrieved from https://lib.dr.iastate.edu/etd/14369

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):

Goswami, Pratik Pran. “Development of light- and chemo-sensitive probes for biochemical methods.” 2015. Thesis, Iowa State University. Accessed February 27, 2021. https://lib.dr.iastate.edu/etd/14369.

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

MLA Handbook (7^th Edition):

Goswami, Pratik Pran. “Development of light- and chemo-sensitive probes for biochemical methods.” 2015. Web. 27 Feb 2021.

Vancouver:

Goswami PP. Development of light- and chemo-sensitive probes for biochemical methods. [Internet] [Thesis]. Iowa State University; 2015. [cited 2021 Feb 27]. Available from: https://lib.dr.iastate.edu/etd/14369.

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

Council of Science Editors:

Goswami PP. Development of light- and chemo-sensitive probes for biochemical methods. [Thesis]. Iowa State University; 2015. Available from: https://lib.dr.iastate.edu/etd/14369

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

University of Oxford

6. Liddon, John Timothy Ruskin. The versatile chemistry of azidoalkyl enol ethers and their equivalents.

Degree: PhD, 2015, University of Oxford

URL: http://ora.ox.ac.uk/objects/uuid:a5554d44-d251-4ca5-8b2d-d07a7c95138a ; http://ethos.bl.uk/OrderDetails.do?uin=uk.bl.ethos.664830

► This thesis describes the synthesis and intramolecular cycloaddition products of azides tethered to olefins bearing a heteroatom in an attempt to access a proposed triazolium… (more)

Subjects/Keywords: 547; Chemistry; Organic Chemistry; Organic

Record Details Similar Records Cite « Share

❌

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

APA (6^th Edition):

Liddon, J. T. R. (2015). The versatile chemistry of azidoalkyl enol ethers and their equivalents. (Doctoral Dissertation). University of Oxford. Retrieved from http://ora.ox.ac.uk/objects/uuid:a5554d44-d251-4ca5-8b2d-d07a7c95138a ; http://ethos.bl.uk/OrderDetails.do?uin=uk.bl.ethos.664830

Chicago Manual of Style (16^th Edition):

Liddon, John Timothy Ruskin. “The versatile chemistry of azidoalkyl enol ethers and their equivalents.” 2015. Doctoral Dissertation, University of Oxford. Accessed February 27, 2021. http://ora.ox.ac.uk/objects/uuid:a5554d44-d251-4ca5-8b2d-d07a7c95138a ; http://ethos.bl.uk/OrderDetails.do?uin=uk.bl.ethos.664830.

MLA Handbook (7^th Edition):

Liddon, John Timothy Ruskin. “The versatile chemistry of azidoalkyl enol ethers and their equivalents.” 2015. Web. 27 Feb 2021.

Vancouver:

Liddon JTR. The versatile chemistry of azidoalkyl enol ethers and their equivalents. [Internet] [Doctoral dissertation]. University of Oxford; 2015. [cited 2021 Feb 27]. Available from: http://ora.ox.ac.uk/objects/uuid:a5554d44-d251-4ca5-8b2d-d07a7c95138a ; http://ethos.bl.uk/OrderDetails.do?uin=uk.bl.ethos.664830.

Council of Science Editors:

Liddon JTR. The versatile chemistry of azidoalkyl enol ethers and their equivalents. [Doctoral Dissertation]. University of Oxford; 2015. Available from: http://ora.ox.ac.uk/objects/uuid:a5554d44-d251-4ca5-8b2d-d07a7c95138a ; http://ethos.bl.uk/OrderDetails.do?uin=uk.bl.ethos.664830

7. Lee, Jennifer Jiyoung. Platform approach to diversification: bio-based methyl coumalate to functionalized aromatics via a Diels-Alder strategy.

Degree: 2014, Iowa State University

URL: https://lib.dr.iastate.edu/etd/14190

► The chemical industry relies on crude oil to manufacture the vast majority of chemicals. However, the increasing demand cannot be supported with the simultaneous decrease… (more)

▼ The chemical industry relies on crude oil to manufacture the vast majority of chemicals. However, the increasing demand cannot be supported with the simultaneous decrease in natural crude oil reserves and increasing prices. Green chemistry solutions may resolve the issue utilizing biorenewable feedstocks, especially for the functionalized aromatic compounds that are ubiquitous in a wide variety of consumer materials. The atom economical Diels-Alder reaction installs two carbon-carbon bonds with high levels of regio-, chemo-, and stereocontrol, which was effectively utilized in a platform approach. Through metabolic engineering, glucose can be converted to malic acid. Afterwards, dimerization and esterification provided the 2-pyrone methyl coumalate as a platform molecule for the methodology. Although unactivated alkenes resulted in aromatic compounds, palladium was required, and with electron-deficient alkene dienophiles, mixtures of regioisomers were observed. In contrast, we developed an inverse electron-demand Diels-Alder/retro-Diels-Alder/elimination domino methodology from methyl coumalate with electron-rich olefins to regioselectively furnish diverse aromatic compounds. Vinyl ether dienophiles provided a broad range of aromatic compounds, which were equipped with an alkoxy leaving group to facilitate aromatization without a catalyst. The scope was expanded with readily prepared acetal and orthoester dienophile equivalents that could be utilized in crude form. As practical bench-stable compounds, elimination occurred under the thermal conditions to reveal the dienophile. The metal-free, one-pot domino sequence efficiently provided high yields and regioselectivities for the desired aromatic compounds. The expansive range of accessible aromatic compounds through the methodology included carbazoles, tricyclic, fused, anisole, and biphenyl systems. Notably, captodative dienophile derivatives from methyl pyruvate provided a 100% biorenewable formal synthesis to terephthalic acid with dimethyl terephthalate as the intermediate. As commodity co-monomers for poly(ethylene terephthalate), the green methodology was further optimized to remove the reaction solvent and recrystallize the product in up to 95% yield. In summary, methyl coumalate represents a convenient bio-based platform for diverse aromatics which fulfills many green chemistry principles in the progress toward a sustainable future.

Subjects/Keywords: Organic Chemistry; Organic Chemistry

3 more images…

Record Details Similar Records Cite « Share

❌

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

APA (6^th Edition):

Lee, J. J. (2014). Platform approach to diversification: bio-based methyl coumalate to functionalized aromatics via a Diels-Alder strategy. (Thesis). Iowa State University. Retrieved from https://lib.dr.iastate.edu/etd/14190

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):

Lee, Jennifer Jiyoung. “Platform approach to diversification: bio-based methyl coumalate to functionalized aromatics via a Diels-Alder strategy.” 2014. Thesis, Iowa State University. Accessed February 27, 2021. https://lib.dr.iastate.edu/etd/14190.

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

MLA Handbook (7^th Edition):

Lee, Jennifer Jiyoung. “Platform approach to diversification: bio-based methyl coumalate to functionalized aromatics via a Diels-Alder strategy.” 2014. Web. 27 Feb 2021.

Vancouver:

Lee JJ. Platform approach to diversification: bio-based methyl coumalate to functionalized aromatics via a Diels-Alder strategy. [Internet] [Thesis]. Iowa State University; 2014. [cited 2021 Feb 27]. Available from: https://lib.dr.iastate.edu/etd/14190.

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

Council of Science Editors:

Lee JJ. Platform approach to diversification: bio-based methyl coumalate to functionalized aromatics via a Diels-Alder strategy. [Thesis]. Iowa State University; 2014. Available from: https://lib.dr.iastate.edu/etd/14190

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

Iowa State University

8. Bhuwalka, Achala. Design and synthesis of novel heterocycles for organic semiconducting materials.

Degree: 2014, Iowa State University

URL: https://lib.dr.iastate.edu/etd/14123

► Organic semiconductors have attracted much attention as alternatives to silicon based photovoltaic technology. Currently, the best power conversion efficiencies use small molecules and conjugated polymers… (more)

Subjects/Keywords: Organic Chemistry; Organic Chemistry

Record Details Similar Records Cite « Share

❌

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

APA (6^th Edition):

Bhuwalka, A. (2014). Design and synthesis of novel heterocycles for organic semiconducting materials. (Thesis). Iowa State University. Retrieved from https://lib.dr.iastate.edu/etd/14123

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):

Bhuwalka, Achala. “Design and synthesis of novel heterocycles for organic semiconducting materials.” 2014. Thesis, Iowa State University. Accessed February 27, 2021. https://lib.dr.iastate.edu/etd/14123.

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

MLA Handbook (7^th Edition):

Bhuwalka, Achala. “Design and synthesis of novel heterocycles for organic semiconducting materials.” 2014. Web. 27 Feb 2021.

Vancouver:

Bhuwalka A. Design and synthesis of novel heterocycles for organic semiconducting materials. [Internet] [Thesis]. Iowa State University; 2014. [cited 2021 Feb 27]. Available from: https://lib.dr.iastate.edu/etd/14123.

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

Council of Science Editors:

Bhuwalka A. Design and synthesis of novel heterocycles for organic semiconducting materials. [Thesis]. Iowa State University; 2014. Available from: https://lib.dr.iastate.edu/etd/14123

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

Wright State University

9. Boyer, Amanda Merrill. Potential Tau Directed Imaging Agents.

Degree: MS, Chemistry, 2015, Wright State University

URL: http://rave.ohiolink.edu/etdc/view?acc_num=wright1453210267

► Given the ambident reactivity of oxindoles in terms of N- versus C-alkylation, realization of the three points of diversity available to (presumably benzenoid substituted) benzylidene… (more)

Subjects/Keywords: Chemistry; Organic Chemistry; chemistry; organic chemistry

Record Details Similar Records Cite « Share

❌

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

APA (6^th Edition):

Boyer, A. M. (2015). Potential Tau Directed Imaging Agents. (Masters Thesis). Wright State University. Retrieved from http://rave.ohiolink.edu/etdc/view?acc_num=wright1453210267

Chicago Manual of Style (16^th Edition):

Boyer, Amanda Merrill. “Potential Tau Directed Imaging Agents.” 2015. Masters Thesis, Wright State University. Accessed February 27, 2021. http://rave.ohiolink.edu/etdc/view?acc_num=wright1453210267.

MLA Handbook (7^th Edition):

Boyer, Amanda Merrill. “Potential Tau Directed Imaging Agents.” 2015. Web. 27 Feb 2021.

Vancouver:

Boyer AM. Potential Tau Directed Imaging Agents. [Internet] [Masters thesis]. Wright State University; 2015. [cited 2021 Feb 27]. Available from: http://rave.ohiolink.edu/etdc/view?acc_num=wright1453210267.

Council of Science Editors:

Boyer AM. Potential Tau Directed Imaging Agents. [Masters Thesis]. Wright State University; 2015. Available from: http://rave.ohiolink.edu/etdc/view?acc_num=wright1453210267

Wayne State University

10. Mandhapati, Appi Reddy. Synthesis of apramycin and paromomycin derivatives as potential next generation aminoglycoside antibiotics and chemistry of isothiocyanato sialyl donors.

Degree: 2016, Wayne State University

URL: http://pqdtopen.proquest.com/#viewpdf?dispub=10153408

► AGAs are clinically important antibacterials for human therapy and have long been used as highly potent antibiotics for treating several bacterial infections. The fidelity… (more)

▼ AGAs are clinically important antibacterials for human therapy and have long been used as highly potent antibiotics for treating several bacterial infections. The fidelity of protein synthesis is affected by AGAs in the course of binding to specific sites of the bacterial rRNA. The clinical use of AGAs and their applications as therapeutics is restricted by toxicity (irreversible ototoxicity and reversible nephrotoxicity) and by the resistance of pathogens. The objective of this research was the development of proficient AGAs that are less toxic (i.e., more selective) and that evade resistance. The first three chapters of this thesis are aimed towards developing new aminoglycoside antibiotics with the emphasis on their chemical synthesis, and the biological evaluation of newly synthesized analogues, as well as the exploration of structure-activity relationships to understand the mechanism of their antimicrobial activity. In particular, studies have focused on the modification of the aminoglycosides apramycin and paromomycin so as to develop the next generation of potent AGAs. Chapter two reveals the importance of the 6' and <i>N</i>7' positions of the apramycin by investigation of the antibacterial activity and antiribosomal activity of the ten apramycin derivatives which were synthesized by modifying these locations. The effect of such modifications on antiribosomal activity is discussed in terms of their influence on drug binding to specific residues in the decoding A site. This information is useful in the development of a structure activity relationship for the antibacterial activity of the apramycin class of aminoglycosides and will also assist in the future design and development of more active and less toxic aminoglycoside antibiotics. Chapter three describes the structure-based design of an improved paromomycin derivative which carries an apramycin-like bicyclic ring I and a conformationally restricted hydroxyl or amine functionality. The influence of the bicyclic paromomycin 6'-hydroxy or amine groups on the binding pattern between AGA and bacterial RNA was investigated by using cell free translational assays. It was found that the bicyclic paromomycin derivative 155 with the equatorial 6’-hydroxy group has a better activity profile than parent paromomycin. In chapter four, an efficient sialyl donor was developed for the challenging α-sialylation by means of a highly electron withdrawing isothiocyanato group incorporated at C-5 position sialic acid. The isothiocyanato sialyl donor 218 proved to be an excellent α-directing group in sialylation for a wide range of acceptors, and provided high yields. Further, the sialylation of corresponding sialyl phosphate donor 231 was also demonstrated to give excellent selectivity, but yields are lower due to competing elimination. In addition, the rich chemistry of isothiocyanate functionality is explored to introduce a variety of novel functionalities at the 5-position of the sialosides including deamination, an alkyl…

Subjects/Keywords: Chemistry; Organic chemistry

Record Details Similar Records Cite « Share

❌

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

APA (6^th Edition):

Mandhapati, A. R. (2016). Synthesis of apramycin and paromomycin derivatives as potential next generation aminoglycoside antibiotics and chemistry of isothiocyanato sialyl donors. (Thesis). Wayne State University. Retrieved from http://pqdtopen.proquest.com/#viewpdf?dispub=10153408

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):

Mandhapati, Appi Reddy. “Synthesis of apramycin and paromomycin derivatives as potential next generation aminoglycoside antibiotics and chemistry of isothiocyanato sialyl donors.” 2016. Thesis, Wayne State University. Accessed February 27, 2021. http://pqdtopen.proquest.com/#viewpdf?dispub=10153408.

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

MLA Handbook (7^th Edition):

Mandhapati, Appi Reddy. “Synthesis of apramycin and paromomycin derivatives as potential next generation aminoglycoside antibiotics and chemistry of isothiocyanato sialyl donors.” 2016. Web. 27 Feb 2021.

Vancouver:

Mandhapati AR. Synthesis of apramycin and paromomycin derivatives as potential next generation aminoglycoside antibiotics and chemistry of isothiocyanato sialyl donors. [Internet] [Thesis]. Wayne State University; 2016. [cited 2021 Feb 27]. Available from: http://pqdtopen.proquest.com/#viewpdf?dispub=10153408.

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

Council of Science Editors:

Mandhapati AR. Synthesis of apramycin and paromomycin derivatives as potential next generation aminoglycoside antibiotics and chemistry of isothiocyanato sialyl donors. [Thesis]. Wayne State University; 2016. Available from: http://pqdtopen.proquest.com/#viewpdf?dispub=10153408

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

11. Omran, Anahid. Synthesis of N-Functionalized Chiral 3-Hydroxyphenylpyrrolidines and Their Evaluation as Selective D3 Receptor Ligands.

Degree: 2017, Southern Illinois University at Edwardsville

URL: http://pqdtopen.proquest.com/#viewpdf?dispub=10616167

► Dysfunction of dopaminergic receptor signaling in the brain is a hallmark of a number of neurodegenerative pathologies. Of the five dopamine receptors, the D₃… (more)

Subjects/Keywords: Chemistry; Organic chemistry

Record Details Similar Records Cite « Share

❌

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

APA (6^th Edition):

Omran, A. (2017). Synthesis of N-Functionalized Chiral 3-Hydroxyphenylpyrrolidines and Their Evaluation as Selective D3 Receptor Ligands. (Thesis). Southern Illinois University at Edwardsville. Retrieved from http://pqdtopen.proquest.com/#viewpdf?dispub=10616167

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):

Omran, Anahid. “Synthesis of N-Functionalized Chiral 3-Hydroxyphenylpyrrolidines and Their Evaluation as Selective D3 Receptor Ligands.” 2017. Thesis, Southern Illinois University at Edwardsville. Accessed February 27, 2021. http://pqdtopen.proquest.com/#viewpdf?dispub=10616167.

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

MLA Handbook (7^th Edition):

Omran, Anahid. “Synthesis of N-Functionalized Chiral 3-Hydroxyphenylpyrrolidines and Their Evaluation as Selective D3 Receptor Ligands.” 2017. Web. 27 Feb 2021.

Vancouver:

Omran A. Synthesis of N-Functionalized Chiral 3-Hydroxyphenylpyrrolidines and Their Evaluation as Selective D3 Receptor Ligands. [Internet] [Thesis]. Southern Illinois University at Edwardsville; 2017. [cited 2021 Feb 27]. Available from: http://pqdtopen.proquest.com/#viewpdf?dispub=10616167.

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

Council of Science Editors:

Omran A. Synthesis of N-Functionalized Chiral 3-Hydroxyphenylpyrrolidines and Their Evaluation as Selective D3 Receptor Ligands. [Thesis]. Southern Illinois University at Edwardsville; 2017. Available from: http://pqdtopen.proquest.com/#viewpdf?dispub=10616167

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

University of California – Irvine

12. Daub, Mary Elisabeth. A Unified Synthetic Approach Toward the Kalihinanes.

Degree: Chemistry, 2016, University of California – Irvine

URL: http://www.escholarship.org/uc/item/5133j2rr

► This dissertation describes our efforts toward developing a unified synthesis of the kalininane family of antimalarial marine isocyanoterpenes. Chapter 1 focuses on the isolation, structure… (more)

Subjects/Keywords: Chemistry; Organic chemistry

Record Details Similar Records Cite « Share

❌

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

APA (6^th Edition):

Daub, M. E. (2016). A Unified Synthetic Approach Toward the Kalihinanes. (Thesis). University of California – Irvine. Retrieved from http://www.escholarship.org/uc/item/5133j2rr

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):

Daub, Mary Elisabeth. “A Unified Synthetic Approach Toward the Kalihinanes.” 2016. Thesis, University of California – Irvine. Accessed February 27, 2021. http://www.escholarship.org/uc/item/5133j2rr.

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

MLA Handbook (7^th Edition):

Daub, Mary Elisabeth. “A Unified Synthetic Approach Toward the Kalihinanes.” 2016. Web. 27 Feb 2021.

Vancouver:

Daub ME. A Unified Synthetic Approach Toward the Kalihinanes. [Internet] [Thesis]. University of California – Irvine; 2016. [cited 2021 Feb 27]. Available from: http://www.escholarship.org/uc/item/5133j2rr.

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

Council of Science Editors:

Daub ME. A Unified Synthetic Approach Toward the Kalihinanes. [Thesis]. University of California – Irvine; 2016. Available from: http://www.escholarship.org/uc/item/5133j2rr

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

University of California – San Diego

13. Hamill, Kristina. Overcoming Biological Barriers: Synthesis and Evaluation of Molecular Transporters.

Degree: Chemistry, 2016, University of California – San Diego

URL: http://www.escholarship.org/uc/item/9p90k8s4

► High molecular weight and highly-charged biomolecules are emerging as drugs with high selectivity and efficacy; however, new strategies are needed to improve their efficiency and… (more)

▼ High molecular weight and highly-charged biomolecules are emerging as drugs with high selectivity and efficacy; however, new strategies are needed to improve their efficiency and targeted delivery in biological systems. One potential solution is the conjugation or association of the biologic with a molecular transporter. Inspired by proteins, such as HIV-Tat, with cellular translocation abilities, numerous guanidinium-rich molecular transporters have been synthesized from a diverse range of nonpeptidic scaffolds. While their repertoire has expanded tremendously in the past two decades, new transporters can provide unique intracellular distributions, targeting effects, or pharmacological properties. Polymyxin B is a cyclic polypeptide antibiotic containing five primary amines and a hydrophobic tail that has not been exploited as a delivery module. Here, we synthesized functionalized derivatives of polymyxin and its per-guanidinylated derivative and evaluated their cellular uptake in mammalian cells. Both polymyxin and its guanidinylated form effectively enter mammalian cells at nanomolar concentrations and can facilitate the cellular delivery of large biomolecules and liposomal assemblies. Guanidinoglycosides are a non-oligomeric class of molecular transporters developed in our lab that permeate the cell membrane through heparan sulfate-dependent pathways at low nanomolar concentrations. To further advance guanidinoglycosides as transporters, guanidinylated neomycin (GNeo) derivatives containing different fatty acids were synthesized and incorporated into liposomes. A small molecule dye or a lysosomal enzyme were encapsulated in the liposomes and delivered to Chinese hamster ovary cells or human fibroblasts, respectively. Incorporation of stearyl- or di-oleyl-GNeo lipids into liposomes resulted in the greatest enhancement of uptake. The delivery of α-L-iduronidase, a lysosomal enzyme, was able to restore enzyme function in fibroblasts lacking endogenous enzyme. As an alternative approach to enhance GNeo as a molecular transporter, oligomers of GNeo were synthesized using ring-opening metathesis polymerization. The synthesis of the reactive monomer, formation of GNeo oligomers, and preliminary cellular uptake studies are presented. In addition to using GNeo for new delivery systems, we also sought to explore the effect the linker connecting the cargo to the carrier has on conjugation and uptake. Varying the length and hydrophobic properties of the linker joining GNeo to biotin resulted in diverse conjugation efficiencies to streptavidin and differences in cellular uptake, highlighting the importance of the linker when designing and studying new molecular transporters.

Subjects/Keywords: Organic chemistry; Chemistry

Record Details Similar Records Cite « Share

❌

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

APA (6^th Edition):

Hamill, K. (2016). Overcoming Biological Barriers: Synthesis and Evaluation of Molecular Transporters. (Thesis). University of California – San Diego. Retrieved from http://www.escholarship.org/uc/item/9p90k8s4

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):

Hamill, Kristina. “Overcoming Biological Barriers: Synthesis and Evaluation of Molecular Transporters.” 2016. Thesis, University of California – San Diego. Accessed February 27, 2021. http://www.escholarship.org/uc/item/9p90k8s4.

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

MLA Handbook (7^th Edition):

Hamill, Kristina. “Overcoming Biological Barriers: Synthesis and Evaluation of Molecular Transporters.” 2016. Web. 27 Feb 2021.

Vancouver:

Hamill K. Overcoming Biological Barriers: Synthesis and Evaluation of Molecular Transporters. [Internet] [Thesis]. University of California – San Diego; 2016. [cited 2021 Feb 27]. Available from: http://www.escholarship.org/uc/item/9p90k8s4.

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

Council of Science Editors:

Hamill K. Overcoming Biological Barriers: Synthesis and Evaluation of Molecular Transporters. [Thesis]. University of California – San Diego; 2016. Available from: http://www.escholarship.org/uc/item/9p90k8s4

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

University of California – Riverside

14. Bastin, Baback. Synthesis of Isotopically Labeled Co-Enzyme to Probe the Active Site of Tryptophan synthase/ New Synthetic Approach to Tetrahydrocannabinol Analogs.

Degree: Chemistry, 2015, University of California – Riverside

URL: http://www.escholarship.org/uc/item/68x2v2nr

► Identifying enzyme mechanisms at proton level resolution is the ultimate goal of enzymology. Traditional enzyme mechanistic studies infer protonation states from x-ray crystal structure and… (more)

Subjects/Keywords: Chemistry; Organic chemistry

Record Details Similar Records Cite « Share

❌

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

APA (6^th Edition):

Bastin, B. (2015). Synthesis of Isotopically Labeled Co-Enzyme to Probe the Active Site of Tryptophan synthase/ New Synthetic Approach to Tetrahydrocannabinol Analogs. (Thesis). University of California – Riverside. Retrieved from http://www.escholarship.org/uc/item/68x2v2nr

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):

Bastin, Baback. “Synthesis of Isotopically Labeled Co-Enzyme to Probe the Active Site of Tryptophan synthase/ New Synthetic Approach to Tetrahydrocannabinol Analogs.” 2015. Thesis, University of California – Riverside. Accessed February 27, 2021. http://www.escholarship.org/uc/item/68x2v2nr.

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

MLA Handbook (7^th Edition):

Bastin, Baback. “Synthesis of Isotopically Labeled Co-Enzyme to Probe the Active Site of Tryptophan synthase/ New Synthetic Approach to Tetrahydrocannabinol Analogs.” 2015. Web. 27 Feb 2021.

Vancouver:

Bastin B. Synthesis of Isotopically Labeled Co-Enzyme to Probe the Active Site of Tryptophan synthase/ New Synthetic Approach to Tetrahydrocannabinol Analogs. [Internet] [Thesis]. University of California – Riverside; 2015. [cited 2021 Feb 27]. Available from: http://www.escholarship.org/uc/item/68x2v2nr.

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

Council of Science Editors:

Bastin B. Synthesis of Isotopically Labeled Co-Enzyme to Probe the Active Site of Tryptophan synthase/ New Synthetic Approach to Tetrahydrocannabinol Analogs. [Thesis]. University of California – Riverside; 2015. Available from: http://www.escholarship.org/uc/item/68x2v2nr

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

UCLA

15. He, Cyndi Qixin. Origins of Reactivity and Selectivity of a Series of Proximity-Induced Transannular Diels-Alder Reactions.

Degree: Chemistry, 2013, UCLA

URL: http://www.escholarship.org/uc/item/4g93x5sn

► Transannular Diels-Alder (TADA) reactions are a powerful tool for the construction of polycyclic structures with four stereogenic centers. A series of remarkably facile and stereoselective… (more)

Subjects/Keywords: Chemistry; Organic chemistry

Record Details Similar Records Cite « Share

❌

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

APA (6^th Edition):

He, C. Q. (2013). Origins of Reactivity and Selectivity of a Series of Proximity-Induced Transannular Diels-Alder Reactions. (Thesis). UCLA. Retrieved from http://www.escholarship.org/uc/item/4g93x5sn

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):

He, Cyndi Qixin. “Origins of Reactivity and Selectivity of a Series of Proximity-Induced Transannular Diels-Alder Reactions.” 2013. Thesis, UCLA. Accessed February 27, 2021. http://www.escholarship.org/uc/item/4g93x5sn.

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

MLA Handbook (7^th Edition):

He, Cyndi Qixin. “Origins of Reactivity and Selectivity of a Series of Proximity-Induced Transannular Diels-Alder Reactions.” 2013. Web. 27 Feb 2021.

Vancouver:

He CQ. Origins of Reactivity and Selectivity of a Series of Proximity-Induced Transannular Diels-Alder Reactions. [Internet] [Thesis]. UCLA; 2013. [cited 2021 Feb 27]. Available from: http://www.escholarship.org/uc/item/4g93x5sn.

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

Council of Science Editors:

He CQ. Origins of Reactivity and Selectivity of a Series of Proximity-Induced Transannular Diels-Alder Reactions. [Thesis]. UCLA; 2013. Available from: http://www.escholarship.org/uc/item/4g93x5sn

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

Temple University

16. GADDIRAJU, NARENDRA VARMA. Asymmetric Synthesis of C-1 Substituted Cocaine Analogues Using Sulfinimine (N-Sulfinyl Imine) Chemistry And Vinylaluminum Addition to Sulfinimines (N-Sulfinyl Imines) For The Asymmetric Synthesis Of Alpha-Substituted-Beta-Amino Esters.

Degree: PhD, 2013, Temple University

URL: http://digital.library.temple.edu/u?/p245801coll10,225834

►

Chemistry

Organic nitrogen containing chiral compounds are widely found in nature, and a number of them exhibit important biological and medicinal properties. The main objective… (more)

▼

Chemistry

Organic nitrogen containing chiral compounds are widely found in nature, and a number of them exhibit important biological and medicinal properties. The main objective of this research is to develop new methods for the asymmetric synthesis of cocaine analogues having methyl (Me), ethyl (Et), n-propyl (n-Pr), n-pentyl (n-C5H11) and phenyl (Ph) groups at the C-1 bridgehead position. The second project concerned the asymmetric synthesis of anti-α-alkyl substituted beta-amino esters, a new chiral building block, utilizing chiral sulfinimine (N-sulfinyl imine) chemistry. The easy availability and abuse of (R)-(-)-cocaine is a global problem and has resulted in many efforts aimed at the preparation of therapeutically useful cocaine analogues. However, to date analogues of cocaine for the treatment of cocaine addiction have not been reported. The requirement of a cis relationship between C-2 and C-3 substituents in the cocaine tropane skeleton where C-2 carbomethoxy group occupies the thermodynamically unfavorable axial position is the main reason for the difficulty in designing efficient asymmetric syntheses of cocaine analogues. In this study, diastereomerically pure N-sulfinyl beta-amino esters were prepared by the addition of the sodium enolate of methyl acetate to masked oxo sulfinimines, novel sulfinimines having a protected carbonyl group. Reduction of the beta-amino esters gave the corresponding beta-amino aldehydes and a Roush-Masamune modified Horner-Wadsworth-Emmons (HWE) reaction afforded the trans-N-sulfinyl alpha,beta-unsaturated delta-amino esters in good yield. Acid hydrolysis of the esters unmasked the carbonyl group and deprotected the amines resulting in an intramolecular cyclization to produce the key dehydropyrrolidines. Regioselective oxidation of the dehydropyrrolidines using catalytic methyl trioxorhenium and urea-hydrogen peroxide gave the corresponding pyrrolidine nitrones in excellent yield. On heating with the Lewis acid catalyst Al(O-t-Bu)3 the nitrones underwent a novel, stereospecific, intramolecular [3+2] cycloaddition reaction to give tricyclic isoxazolidines. Importantly, the isoxazolidine establishes the necessary cis relationship between C-2 and C-3 substituents in cocaine skeleton. The tricyclic isoxazolidines were readily converted to the N-Me quaternary ammonium salts on heating with methylmethanesulfonate and hydrogenolysis with Pd/C at 1 atm of H2 cleave the N-O bond to afford the ecgonine methyl ester, the tropane alcohol. In contrast to other C-3 (R = Me, Et, n-Pr, Ph) isoxazolidine quaternary ammonium salts, the C-3 n-C5H11 analogue did not undergo N-O bond cleavage under the hydrogenolysis conditions. This analogue rearrange to a bridged bicyclic [4.2.1]isoxazolidine. It was found that all C-3 isoxazolidine N-Me quaternary ammonium salts undergo this rearrangement on treatment with triethylamine. Fortunately, hydrogenolysis of n-C5H11 isoxazolidine quaternary ammonium salt at 4 atm of H2 cleaved the N-O bond to give the desired alcohol, ecgonine methyl ester.…

Advisors/Committee Members: Davis, Franklin A.;, Andrade, Rodrigo B., Wuest, William M., Cannon, Kevin C.;.

Subjects/Keywords: Chemistry; Organic chemistry

Record Details Similar Records Cite « Share

❌

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

APA (6^th Edition):

GADDIRAJU, N. V. (2013). Asymmetric Synthesis of C-1 Substituted Cocaine Analogues Using Sulfinimine (N-Sulfinyl Imine) Chemistry And Vinylaluminum Addition to Sulfinimines (N-Sulfinyl Imines) For The Asymmetric Synthesis Of Alpha-Substituted-Beta-Amino Esters. (Doctoral Dissertation). Temple University. Retrieved from http://digital.library.temple.edu/u?/p245801coll10,225834

Chicago Manual of Style (16^th Edition):

GADDIRAJU, NARENDRA VARMA. “Asymmetric Synthesis of C-1 Substituted Cocaine Analogues Using Sulfinimine (N-Sulfinyl Imine) Chemistry And Vinylaluminum Addition to Sulfinimines (N-Sulfinyl Imines) For The Asymmetric Synthesis Of Alpha-Substituted-Beta-Amino Esters.” 2013. Doctoral Dissertation, Temple University. Accessed February 27, 2021. http://digital.library.temple.edu/u?/p245801coll10,225834.

MLA Handbook (7^th Edition):

GADDIRAJU, NARENDRA VARMA. “Asymmetric Synthesis of C-1 Substituted Cocaine Analogues Using Sulfinimine (N-Sulfinyl Imine) Chemistry And Vinylaluminum Addition to Sulfinimines (N-Sulfinyl Imines) For The Asymmetric Synthesis Of Alpha-Substituted-Beta-Amino Esters.” 2013. Web. 27 Feb 2021.

Vancouver:

GADDIRAJU NV. Asymmetric Synthesis of C-1 Substituted Cocaine Analogues Using Sulfinimine (N-Sulfinyl Imine) Chemistry And Vinylaluminum Addition to Sulfinimines (N-Sulfinyl Imines) For The Asymmetric Synthesis Of Alpha-Substituted-Beta-Amino Esters. [Internet] [Doctoral dissertation]. Temple University; 2013. [cited 2021 Feb 27]. Available from: http://digital.library.temple.edu/u?/p245801coll10,225834.

Council of Science Editors:

GADDIRAJU NV. Asymmetric Synthesis of C-1 Substituted Cocaine Analogues Using Sulfinimine (N-Sulfinyl Imine) Chemistry And Vinylaluminum Addition to Sulfinimines (N-Sulfinyl Imines) For The Asymmetric Synthesis Of Alpha-Substituted-Beta-Amino Esters. [Doctoral Dissertation]. Temple University; 2013. Available from: http://digital.library.temple.edu/u?/p245801coll10,225834

17. Guerrera, Cessandra. Stereoselective Synthesis of alpha,alpha-Disubstituted Amino Acids Utilizing Porcine Liver Esterase and the Petasis Borono-Mannich Reaction.

Degree: 2017, Southern Connecticut State University

URL: http://pqdtopen.proquest.com/#viewpdf?dispub=10283110

► Arginase is a manganese-containing enzyme that catalyzes the hydrolysis of L-arginine to yield L-ornithine and urea. It has been suggested that inhibition of arginase… (more)

Subjects/Keywords: Chemistry; Organic chemistry

Record Details Similar Records Cite « Share

❌

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

APA (6^th Edition):

Guerrera, C. (2017). Stereoselective Synthesis of alpha,alpha-Disubstituted Amino Acids Utilizing Porcine Liver Esterase and the Petasis Borono-Mannich Reaction. (Thesis). Southern Connecticut State University. Retrieved from http://pqdtopen.proquest.com/#viewpdf?dispub=10283110

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):

Guerrera, Cessandra. “Stereoselective Synthesis of alpha,alpha-Disubstituted Amino Acids Utilizing Porcine Liver Esterase and the Petasis Borono-Mannich Reaction.” 2017. Thesis, Southern Connecticut State University. Accessed February 27, 2021. http://pqdtopen.proquest.com/#viewpdf?dispub=10283110.

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

MLA Handbook (7^th Edition):

Guerrera, Cessandra. “Stereoselective Synthesis of alpha,alpha-Disubstituted Amino Acids Utilizing Porcine Liver Esterase and the Petasis Borono-Mannich Reaction.” 2017. Web. 27 Feb 2021.

Vancouver:

Guerrera C. Stereoselective Synthesis of alpha,alpha-Disubstituted Amino Acids Utilizing Porcine Liver Esterase and the Petasis Borono-Mannich Reaction. [Internet] [Thesis]. Southern Connecticut State University; 2017. [cited 2021 Feb 27]. Available from: http://pqdtopen.proquest.com/#viewpdf?dispub=10283110.

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

Council of Science Editors:

Guerrera C. Stereoselective Synthesis of alpha,alpha-Disubstituted Amino Acids Utilizing Porcine Liver Esterase and the Petasis Borono-Mannich Reaction. [Thesis]. Southern Connecticut State University; 2017. Available from: http://pqdtopen.proquest.com/#viewpdf?dispub=10283110

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

18. Borikar, Sanjay P. Novel organic transformations using ultrasound Ionic liquid and their application towards the synthesis of biological active molecules/intermediates.

Degree: 2011, University of Pune

URL: http://shodhganga.inflibnet.ac.in/handle/10603/2375

► “Novel Organic Transformations Using Ultrasound, Ionic Liquid and Their Application Towards the Synthesis of Biological Active Molecules/Intermediates” Thesis is divided into three chapters: CHAPTER-1: Synthesis… (more)

Subjects/Keywords: Chemistry; Organic Chemistry

Record Details Similar Records Cite « Share

❌

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

APA (6^th Edition):

Borikar, S. P. (2011). Novel organic transformations using ultrasound Ionic liquid and their application towards the synthesis of biological active molecules/intermediates. (Thesis). University of Pune. Retrieved from http://shodhganga.inflibnet.ac.in/handle/10603/2375

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):

Borikar, Sanjay P. “Novel organic transformations using ultrasound Ionic liquid and their application towards the synthesis of biological active molecules/intermediates.” 2011. Thesis, University of Pune. Accessed February 27, 2021. http://shodhganga.inflibnet.ac.in/handle/10603/2375.

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

MLA Handbook (7^th Edition):

Borikar, Sanjay P. “Novel organic transformations using ultrasound Ionic liquid and their application towards the synthesis of biological active molecules/intermediates.” 2011. Web. 27 Feb 2021.

Vancouver:

Borikar SP. Novel organic transformations using ultrasound Ionic liquid and their application towards the synthesis of biological active molecules/intermediates. [Internet] [Thesis]. University of Pune; 2011. [cited 2021 Feb 27]. Available from: http://shodhganga.inflibnet.ac.in/handle/10603/2375.

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

Council of Science Editors:

Borikar SP. Novel organic transformations using ultrasound Ionic liquid and their application towards the synthesis of biological active molecules/intermediates. [Thesis]. University of Pune; 2011. Available from: http://shodhganga.inflibnet.ac.in/handle/10603/2375

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

19. Ayala, Malerie. Synthesis of a second generation naphthopyran metal-binding photoswitch.

Degree: 2015, California State University, Los Angeles

URL: http://pqdtopen.proquest.com/#viewpdf?dispub=1597156

► The aim of this project was to increase the calcium binding affinity of our previously developed photochromic 3H-naphtho[2,1-b]pyran <b>1,</b> a light-controlled reversible binding switch… (more)

Subjects/Keywords: Chemistry; Organic chemistry

Record Details Similar Records Cite « Share

❌

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

APA (6^th Edition):

Ayala, M. (2015). Synthesis of a second generation naphthopyran metal-binding photoswitch. (Thesis). California State University, Los Angeles. Retrieved from http://pqdtopen.proquest.com/#viewpdf?dispub=1597156

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):

Ayala, Malerie. “Synthesis of a second generation naphthopyran metal-binding photoswitch.” 2015. Thesis, California State University, Los Angeles. Accessed February 27, 2021. http://pqdtopen.proquest.com/#viewpdf?dispub=1597156.

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

MLA Handbook (7^th Edition):

Ayala, Malerie. “Synthesis of a second generation naphthopyran metal-binding photoswitch.” 2015. Web. 27 Feb 2021.

Vancouver:

Ayala M. Synthesis of a second generation naphthopyran metal-binding photoswitch. [Internet] [Thesis]. California State University, Los Angeles; 2015. [cited 2021 Feb 27]. Available from: http://pqdtopen.proquest.com/#viewpdf?dispub=1597156.

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

Council of Science Editors:

Ayala M. Synthesis of a second generation naphthopyran metal-binding photoswitch. [Thesis]. California State University, Los Angeles; 2015. Available from: http://pqdtopen.proquest.com/#viewpdf?dispub=1597156

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

Iowa State University

20. Weerasekara, Sagarika Tharangie. Enantioselective epoxidation catalyzed by manganese-substituted human carbonic anhydrase.

Degree: 2015, Iowa State University

URL: https://lib.dr.iastate.edu/etd/14900

► Artificial metalloenzymes are an important class of hybrid catalysts for enantioselective, regioselective and chemoselective organic transformations. Despite several limitations associated with this type of hybrid… (more)

Subjects/Keywords: Organic Chemistry; Chemistry

Record Details Similar Records Cite « Share

❌

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

APA (6^th Edition):

Weerasekara, S. T. (2015). Enantioselective epoxidation catalyzed by manganese-substituted human carbonic anhydrase. (Thesis). Iowa State University. Retrieved from https://lib.dr.iastate.edu/etd/14900

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):

Weerasekara, Sagarika Tharangie. “Enantioselective epoxidation catalyzed by manganese-substituted human carbonic anhydrase.” 2015. Thesis, Iowa State University. Accessed February 27, 2021. https://lib.dr.iastate.edu/etd/14900.

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

MLA Handbook (7^th Edition):

Weerasekara, Sagarika Tharangie. “Enantioselective epoxidation catalyzed by manganese-substituted human carbonic anhydrase.” 2015. Web. 27 Feb 2021.

Vancouver:

Weerasekara ST. Enantioselective epoxidation catalyzed by manganese-substituted human carbonic anhydrase. [Internet] [Thesis]. Iowa State University; 2015. [cited 2021 Feb 27]. Available from: https://lib.dr.iastate.edu/etd/14900.

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

Council of Science Editors:

Weerasekara ST. Enantioselective epoxidation catalyzed by manganese-substituted human carbonic anhydrase. [Thesis]. Iowa State University; 2015. Available from: https://lib.dr.iastate.edu/etd/14900

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

Wayne State University

21. Sharma, Indrajeet. Chemical Synthesis Of Peptides And Peptide Thioesters.

Degree: PhD, Chemistry, 2011, Wayne State University

URL: https://digitalcommons.wayne.edu/oa_dissertations/205

► This dissertation describes investigations toward the development of a new chemistry for the block synthesis of peptides and peptidyl thioesters. A direct approach for… (more)

▼ This dissertation describes investigations toward the development of a new chemistry for the block synthesis of peptides and peptidyl thioesters. A direct approach for the Fmoc-SPPS of peptidyl thioesters is also delineated in this thesis. In the first part of chapter one, the difficulty and importance of chemical synthesis of peptides is explained, and a brief survey of available methods is given. The second part of chapter one presents the challenges inherent in the synthesis of peptidyl thioesters by Fmoc-SPPS. The second chapter outlines the investigations conducted towards the development of a new chemistry for epimerization-free block synthesis of peptides from thioacids and amines by a process involving the in situ formation of highly active thioesters by nucleophilic aromatic substitution of C-terminal thioacids on electron-deficient halogenoarenes. The superiority of this new chemistry over available methods is illustrated through direct comparisons in the block synthesis of an octapeptide. In chapter three, studies carried out to probe the reactivity of N-terminal sulfonamides towards peptidyl thioacids are presented. Studies directed at determining the optimal sulfonamide for use in convergent multiple peptide fragment ligation are presented as is the application of these sulfonamides in both left to right and right to left block synthesis of peptides.. Model studies on the development of an intramolecular variant of the thioacid/sulfonamide coupling are also presented in this chapter. Continuing the theme, Chapter 4 presents studies undertaken with the goal of developing a direct method for the efficient synthesis of peptidyl thioesters by the widely used Fmoc-SPPS chemistry. A method to construct the thioester functionality from thioamides is described based on alkylation to give an intermediate thioimide and its subsequent hydrolysis. The application of this methodology to the synthesis of functionality diverse oligo-peptide thioesters is also presented. In chapter five, the overall conclusions of the dissertation are presented, while in chapter six, the experimental procedures and characterization data for the synthesized compounds are documented. Advisors/Committee Members: DAVID CRICH.

Subjects/Keywords: Chemistry; Organic Chemistry

Record Details Similar Records Cite « Share

❌

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

APA (6^th Edition):

Sharma, I. (2011). Chemical Synthesis Of Peptides And Peptide Thioesters. (Doctoral Dissertation). Wayne State University. Retrieved from https://digitalcommons.wayne.edu/oa_dissertations/205

Chicago Manual of Style (16^th Edition):

Sharma, Indrajeet. “Chemical Synthesis Of Peptides And Peptide Thioesters.” 2011. Doctoral Dissertation, Wayne State University. Accessed February 27, 2021. https://digitalcommons.wayne.edu/oa_dissertations/205.

MLA Handbook (7^th Edition):

Sharma, Indrajeet. “Chemical Synthesis Of Peptides And Peptide Thioesters.” 2011. Web. 27 Feb 2021.

Vancouver:

Sharma I. Chemical Synthesis Of Peptides And Peptide Thioesters. [Internet] [Doctoral dissertation]. Wayne State University; 2011. [cited 2021 Feb 27]. Available from: https://digitalcommons.wayne.edu/oa_dissertations/205.

Council of Science Editors:

Sharma I. Chemical Synthesis Of Peptides And Peptide Thioesters. [Doctoral Dissertation]. Wayne State University; 2011. Available from: https://digitalcommons.wayne.edu/oa_dissertations/205

University of Wisconsin – Milwaukee

22. Poe, Michael M. Synthesis of Subtype Selective Bz/GABAA Receptor Ligands for the Treatment of Anxiety, Epilepsy and Neuropathic Pain, as Well as Schizophrenia and Asthma.

Degree: PhD, Chemistry, 2016, University of Wisconsin – Milwaukee

URL: https://dc.uwm.edu/etd/1301

► The α2/α3 subtype selective Bz/GABAA receptor positive allosteric modulator HZ-166 (3) has been shown to be a nonsedating anxiolytic with anticonvulsant and antihyperalgesic activity.… (more)

▼ The α2/α3 subtype selective Bz/GABAA receptor positive allosteric modulator HZ-166 (3) has been shown to be a nonsedating anxiolytic with anticonvulsant and antihyperalgesic activity. However, instability in vitro and in vivo has hindered its advancement into clinical trials. A series of ligands based off HZ-166 (3) were synthesized. Many of these ligands were designed to increase metabolic stability, while others were synthesized to study the effects that electronics and sterics have on the efficacy exerted when bound to the GABAA receptor. The α3 subtype selective methyl ester MP-III-024 (19) was shown to have increased resistance to metabolism in in vitro liver microsomal studies and exhibited significant anxiolytic and antihyperalgesic effects in mice without showing signs of sedation. However, pharmacokinetic studies indicated that esters as a functional group may not be suitable for extensive preclinical studies. A series of heterocyclic bioisosteres were synthesized to specifically overcome short half-lives in vivo. The oxadiazole MP-III-080 (34) and oxazole KRM-II-81 (36) underwent pharmacokinetic studies and were both found to exist in plasma and brain samples in high levels. These results indicated that these and related heterocycles would be stable in vivo to undergo extensive preclinical trials. A dozen ligands were assessed in vivo in an anxiolytic marble burying assay and a rotarod assay designed to measure ataxic effects. The results from these studies and other in vitro protocols led to additional studies using KRM-II-81 (36). This oxazole 36 was found to exhibit significant anxiolytic and anticonvulsant properties, including reducing network firing rate frequency in human brain tissue from a patient suffering from resistance epilepsy. In addition, KRM-II-81 (36) was found to be more efficacious than gabapentin to reverse the effects of hyperalgesia in a neuropathic pain model at a lower dose using rats, as well as exhibiting antidepressant-like effects. The α5 GABAA receptor subtype has been linked to the cognitive disorders in such diseases as schizophrenia, bipolar I disorder and major depressive disorder. The enantiomers SH-053-2'F-S-CH3 (51) and SH-053-2'F-R-CH3 (52) have been shown to be α2/α3/α5- and α5- subtype selective agonists, respectively. Both ligands (S)-51 and (R)-52 have been shown to reduce some positive symptoms of schizophrenia; the S-enantiomer 51 was active in the poly(I:C) model of schizophrenia while the R-enantiomer 52 was active in the MAM-model of schizophrenia. Due to the high rate of comorbidity of schizophrenia with anxiety, epilepsy and depression, the S-enatiomer (51) is shown here to be useful in these instances exhibiting anxiolytic and anticonvulsant properties. In addition, work on analogs of 52 produced MP-III-004 (63), an α5 subtype selective ligand with reduced efficacy at the α1, α2 and α3 subtypes as compared to 52, as well as the very potent α5 positive allosteric modulator MP-III-022 (65). This methyl amide 65 was shown to activate α5… Advisors/Committee Members: James M. Cook.

Subjects/Keywords: Chemistry; Organic Chemistry

Record Details Similar Records Cite « Share

❌

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

APA (6^th Edition):

Poe, M. M. (2016). Synthesis of Subtype Selective Bz/GABAA Receptor Ligands for the Treatment of Anxiety, Epilepsy and Neuropathic Pain, as Well as Schizophrenia and Asthma. (Doctoral Dissertation). University of Wisconsin – Milwaukee. Retrieved from https://dc.uwm.edu/etd/1301

Chicago Manual of Style (16^th Edition):

Poe, Michael M. “Synthesis of Subtype Selective Bz/GABAA Receptor Ligands for the Treatment of Anxiety, Epilepsy and Neuropathic Pain, as Well as Schizophrenia and Asthma.” 2016. Doctoral Dissertation, University of Wisconsin – Milwaukee. Accessed February 27, 2021. https://dc.uwm.edu/etd/1301.

MLA Handbook (7^th Edition):

Poe, Michael M. “Synthesis of Subtype Selective Bz/GABAA Receptor Ligands for the Treatment of Anxiety, Epilepsy and Neuropathic Pain, as Well as Schizophrenia and Asthma.” 2016. Web. 27 Feb 2021.

Vancouver:

Poe MM. Synthesis of Subtype Selective Bz/GABAA Receptor Ligands for the Treatment of Anxiety, Epilepsy and Neuropathic Pain, as Well as Schizophrenia and Asthma. [Internet] [Doctoral dissertation]. University of Wisconsin – Milwaukee; 2016. [cited 2021 Feb 27]. Available from: https://dc.uwm.edu/etd/1301.

Council of Science Editors:

Poe MM. Synthesis of Subtype Selective Bz/GABAA Receptor Ligands for the Treatment of Anxiety, Epilepsy and Neuropathic Pain, as Well as Schizophrenia and Asthma. [Doctoral Dissertation]. University of Wisconsin – Milwaukee; 2016. Available from: https://dc.uwm.edu/etd/1301

23. Shadrick, Melanie. Effect of C-7,8 di-Picoloyl in Sialylation Reactions.

Degree: 2018, Southern Illinois University at Edwardsville

URL: http://pqdtopen.proquest.com/#viewpdf?dispub=10808011

► N-acetyl neuraminic acid is most common member of the sialic acid family. This unique monosaccharide is displayed at the terminal position of oligosaccharides in… (more)

Subjects/Keywords: Chemistry; Organic chemistry

Record Details Similar Records Cite « Share

❌

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

APA (6^th Edition):

Shadrick, M. (2018). Effect of C-7,8 di-Picoloyl in Sialylation Reactions. (Thesis). Southern Illinois University at Edwardsville. Retrieved from http://pqdtopen.proquest.com/#viewpdf?dispub=10808011

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):

Shadrick, Melanie. “Effect of C-7,8 di-Picoloyl in Sialylation Reactions.” 2018. Thesis, Southern Illinois University at Edwardsville. Accessed February 27, 2021. http://pqdtopen.proquest.com/#viewpdf?dispub=10808011.

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

MLA Handbook (7^th Edition):

Shadrick, Melanie. “Effect of C-7,8 di-Picoloyl in Sialylation Reactions.” 2018. Web. 27 Feb 2021.

Vancouver:

Shadrick M. Effect of C-7,8 di-Picoloyl in Sialylation Reactions. [Internet] [Thesis]. Southern Illinois University at Edwardsville; 2018. [cited 2021 Feb 27]. Available from: http://pqdtopen.proquest.com/#viewpdf?dispub=10808011.

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

Council of Science Editors:

Shadrick M. Effect of C-7,8 di-Picoloyl in Sialylation Reactions. [Thesis]. Southern Illinois University at Edwardsville; 2018. Available from: http://pqdtopen.proquest.com/#viewpdf?dispub=10808011

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

24. Lippincott, Daniel John. Allenes, Alkenes & Alkynes| My Piece of the pi ...in Water at Room Temperature...

Degree: 2019, University of California, Santa Barbara

URL: http://pqdtopen.proquest.com/#viewpdf?dispub=10982306

► I. An environmentally responsible, mild method for the synthesis of functionalized 1,3-butadienes is presented. It utilizes allenic esters of varying substitution patterns, as well… (more)

Subjects/Keywords: Chemistry; Organic chemistry

Record Details Similar Records Cite « Share

❌

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

APA (6^th Edition):

Lippincott, D. J. (2019). Allenes, Alkenes & Alkynes| My Piece of the pi ...in Water at Room Temperature... (Thesis). University of California, Santa Barbara. Retrieved from http://pqdtopen.proquest.com/#viewpdf?dispub=10982306

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):

Lippincott, Daniel John. “Allenes, Alkenes & Alkynes| My Piece of the pi ...in Water at Room Temperature...” 2019. Thesis, University of California, Santa Barbara. Accessed February 27, 2021. http://pqdtopen.proquest.com/#viewpdf?dispub=10982306.

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

MLA Handbook (7^th Edition):

Lippincott, Daniel John. “Allenes, Alkenes & Alkynes| My Piece of the pi ...in Water at Room Temperature...” 2019. Web. 27 Feb 2021.

Vancouver:

Lippincott DJ. Allenes, Alkenes & Alkynes| My Piece of the pi ...in Water at Room Temperature... [Internet] [Thesis]. University of California, Santa Barbara; 2019. [cited 2021 Feb 27]. Available from: http://pqdtopen.proquest.com/#viewpdf?dispub=10982306.

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

Council of Science Editors:

Lippincott DJ. Allenes, Alkenes & Alkynes| My Piece of the pi ...in Water at Room Temperature... [Thesis]. University of California, Santa Barbara; 2019. Available from: http://pqdtopen.proquest.com/#viewpdf?dispub=10982306

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

University of Vermont

25. Machamer, Natalie Kay. I. A New Route To Azomethine Ylides: Shifting The Reliance On Amino Ester Precursors II. Applications In Total Synthesis.

Degree: PhD, Chemistry, 2015, University of Vermont

URL: https://scholarworks.uvm.edu/graddis/407

► Nitrogen-containing heterocycles have great utility in the biomedical and medicinal fields and one such heterocycle is the 5-membered pyrrolidine ring. The synthesis of pyrrolidine… (more)

▼ Nitrogen-containing heterocycles have great utility in the biomedical and medicinal fields and one such heterocycle is the 5-membered pyrrolidine ring. The synthesis of pyrrolidine rings has been studied extensively with the routes relying on anodic oxidation, transition metals and dipolar cycloadditions with azomethine ylides. Previous work in the Waters group has been focused on new routes to azomethine ylides through a domino sequence. Through a thermal aza-Cope rearrangement followed by [3+2] dipolar cycloaddition the synthesis of a library of 2-allyl pyrrolidines was accomplished. It was discovered that by using allylic amines and glyoxals at room temperature a cycloadduct was isolated bearing a 5-vinyl moiety. The results were promising and the first part of the project was to optimize the reaction followed by substrate scope expansion to build a library of compounds. The new cycloadducts could not have been synthesized under traditional methods due to side reactivity difficulties and therefore this work circumvents the problems associated with the classical routes. This is the first report of azomethine ylides derived from allylic amines and glyoxals to date. Many cycloadducts were synthesized and they all contained the 5-alkenyl group with many of them closely matching pyrrolidine containing natural products. The natural product, spirotryprostatin B, is an ideal target for featuring the developed methodology in total synthesis. Spirotryprostatin B was found to inhibit the G2/M phase in the cell replication pathway, suggesting a possible anti-cancer treatment. Using allylamine, ethyl glyoxylate, and appropriate dipolarophile under the optimized reaction conditions would afford a highly substituted cycloadduct that could be transformed into the final target. The core of the structure was synthesized in just three steps with only two steps requiring purification. The regio- and stereochemistry of the cycloadducts were analyzed using NOE enhancement and DFT studies to conclude that the [3+2] dipolar cycloaddition proceeded through the exo transition state. The total synthesis of the anti-cancer compound peducularine was also studied. Many different dipolarophiles were tested, but the ideal dipolarophile was not identified. The results of these experiments were important in defining the scope of the methodology. Advisors/Committee Members: Stephen P. Waters.

Subjects/Keywords: Chemistry; Organic Chemistry

Record Details Similar Records Cite « Share

❌

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

APA (6^th Edition):

Machamer, N. K. (2015). I. A New Route To Azomethine Ylides: Shifting The Reliance On Amino Ester Precursors II. Applications In Total Synthesis. (Doctoral Dissertation). University of Vermont. Retrieved from https://scholarworks.uvm.edu/graddis/407

Chicago Manual of Style (16^th Edition):

Machamer, Natalie Kay. “I. A New Route To Azomethine Ylides: Shifting The Reliance On Amino Ester Precursors II. Applications In Total Synthesis.” 2015. Doctoral Dissertation, University of Vermont. Accessed February 27, 2021. https://scholarworks.uvm.edu/graddis/407.

MLA Handbook (7^th Edition):

Machamer, Natalie Kay. “I. A New Route To Azomethine Ylides: Shifting The Reliance On Amino Ester Precursors II. Applications In Total Synthesis.” 2015. Web. 27 Feb 2021.

Vancouver:

Machamer NK. I. A New Route To Azomethine Ylides: Shifting The Reliance On Amino Ester Precursors II. Applications In Total Synthesis. [Internet] [Doctoral dissertation]. University of Vermont; 2015. [cited 2021 Feb 27]. Available from: https://scholarworks.uvm.edu/graddis/407.

Council of Science Editors:

Machamer NK. I. A New Route To Azomethine Ylides: Shifting The Reliance On Amino Ester Precursors II. Applications In Total Synthesis. [Doctoral Dissertation]. University of Vermont; 2015. Available from: https://scholarworks.uvm.edu/graddis/407

Wayne State University

26. Amarasekara, Harsha Chandhana. Influence Of Side Chain Conformation On The Mechanism(s) Of Glycosylation Reactions; Investigation Of Sialidation Reaction Mechanism(s) By Kinetic Studies.

Degree: PhD, Chemistry, 2019, Wayne State University

URL: https://digitalcommons.wayne.edu/oa_dissertations/2138

► Glycosylation, being the key reaction of glycobiology and carbohydrate chemistry, demands robust and stereoselective glycosylation methods. The rational development of such methods necessitates knowledge… (more)

▼ Glycosylation, being the key reaction of glycobiology and carbohydrate chemistry, demands robust and stereoselective glycosylation methods. The rational development of such methods necessitates knowledge of the glycosylation reaction mechanism and the factors influencing glycosylation reactions. The work discussed in this dissertation is focused on studying glycosylation reaction mechanisms and exploring the key factors influencing them. Chapter one reviews the background to the research, starting with a brief introduction of the significance of carbohydrates as structural and energy-storage materials. The significance of cell surface carbohydrates and their roles in communication and related processes are discussed along with examples of their applications in biology and therapeutics. Approaches to the synthesis of carbohydrates, glycosylation reactions, and their mechanisms are then discussed. The stability of glycosyl oxocarbenium ions and the influence of protecting groups on oxocarbenium ions are also discussed. This chapter ends with a short description of neighboring group participation. Chapter two describes the synthesis of a series of oxabicyclo[4.4.0]decane type compounds as models representing the ideal gg, gt, and tg conformations of the pyranoside side chain, and the derivation of experimental limiting coupling constants from them. The preparation of the model compounds, NMR analysis, triage of some compounds on the grounds of lack of conformational purity, derivation of correction factors, and finally, the application of limiting coupling constants in the calculation of side chain population are described. The absence of negative populations on the application of the limiting coupling constants to a series of literature compounds reveals the reliability of the new limiting data set. Chapter three discusses the influence of protecting groups on the modulation of side chain conformation and the subsequent impact on the glycosylation reactions. The synthesis of a series of 4-O-derivatives of galacto- and glucopyranosides and 6-O- derivatives of glucopyranosides, their NMR analysis, and calculation of their side chain populations, and their correlation with the anomeric reactivity are discussed. Both aroyl and alkanoyl esters modulate the side chain population and moderate the electron withdrawing effects of the ester, whereas, the 4-O-esters of glucopyranosides change the side chain conformation to support the electron withdrawing effect of the ester. In both the galacto- and glucopyranose 4-O-series, highly electron withdrawing esters, such as trifluoroacetyl and trichloroacetyl esters, modulate the side chain conformation to reinforce the electron withdrawing effect of the esters. The glucopyranose 6-O-series did not show any significant modulatory effects as a function of protecting groups. Overall, this study reveals small but consistent changes in the side chain population, with corresponding small influences on glycosylation reactions. … Advisors/Committee Members: David Crich.

Subjects/Keywords: Chemistry; Organic Chemistry

Record Details Similar Records Cite « Share

❌

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

APA (6^th Edition):

Amarasekara, H. C. (2019). Influence Of Side Chain Conformation On The Mechanism(s) Of Glycosylation Reactions; Investigation Of Sialidation Reaction Mechanism(s) By Kinetic Studies. (Doctoral Dissertation). Wayne State University. Retrieved from https://digitalcommons.wayne.edu/oa_dissertations/2138

Chicago Manual of Style (16^th Edition):

Amarasekara, Harsha Chandhana. “Influence Of Side Chain Conformation On The Mechanism(s) Of Glycosylation Reactions; Investigation Of Sialidation Reaction Mechanism(s) By Kinetic Studies.” 2019. Doctoral Dissertation, Wayne State University. Accessed February 27, 2021. https://digitalcommons.wayne.edu/oa_dissertations/2138.

MLA Handbook (7^th Edition):

Amarasekara, Harsha Chandhana. “Influence Of Side Chain Conformation On The Mechanism(s) Of Glycosylation Reactions; Investigation Of Sialidation Reaction Mechanism(s) By Kinetic Studies.” 2019. Web. 27 Feb 2021.

Vancouver:

Amarasekara HC. Influence Of Side Chain Conformation On The Mechanism(s) Of Glycosylation Reactions; Investigation Of Sialidation Reaction Mechanism(s) By Kinetic Studies. [Internet] [Doctoral dissertation]. Wayne State University; 2019. [cited 2021 Feb 27]. Available from: https://digitalcommons.wayne.edu/oa_dissertations/2138.

Council of Science Editors:

Amarasekara HC. Influence Of Side Chain Conformation On The Mechanism(s) Of Glycosylation Reactions; Investigation Of Sialidation Reaction Mechanism(s) By Kinetic Studies. [Doctoral Dissertation]. Wayne State University; 2019. Available from: https://digitalcommons.wayne.edu/oa_dissertations/2138

Wayne State University

27. Li, Ao. Design Of Ruthenium(ii) Polypyridyl Complexes For Effectively Caging Nitriles And Aromatic Heterocycles.

Degree: PhD, Chemistry, 2018, Wayne State University

URL: https://digitalcommons.wayne.edu/oa_dissertations/2043

► ABSTRACT DESIGN OF RUTHENIUM(II) POLYPYRIDYL COMPLEXES FOR EFFECTIVELY CAGING NITRILES AND AROMATIC HETEROCYCLES by AO LI May 2018 Advisor: Dr. Jeremy Kodanko Major: Chemistry… (more)

▼ ABSTRACT DESIGN OF RUTHENIUM(II) POLYPYRIDYL COMPLEXES FOR EFFECTIVELY CAGING NITRILES AND AROMATIC HETEROCYCLES by AO LI May 2018 Advisor: Dr. Jeremy Kodanko Major: Chemistry Degree: Doctor of Philosophy Ru(II) polypyridyl complexes have been frequently employed in the caging and photorelease of biologically active compounds. Traditional photocaging groups derived from Ru(II) have been largely based on bi- or tridentate ancillary ligands, and those bearing ancillary ligands with high-denticities are yet to be developed. Exploring Ru(II) polypyridyl complexes possessing ancillary ligands with high-denticities provides insight into the photophysical and photochemical properties of ruthenium complexes, which creates novel prospects in the design of ruthenium complexes applicable towards photoactivated drug delivery and energy conversion.In this thesis, we present a series of Ru(II)-based photocages derived from tetradentate ancillary ligands TPA and cyTPA that have been developed as effective photocaging groups for nitriles and aromatic heterocycles. All complexes exhibit excellent stability in the dark and selectively release the caged nitriles and aromatic heterocycles upon irradiation with light. My findings contribute to showing that Ru(TPA) is appropriate as a photochemical agent to offer precise control over biological activity without undesired toxicity. In addition, the results in this thesis reveal a transtype effect that significantly promotes ligand photodissociation in Ru(II) polypyridyl complexes,where a complex presents a highly mixed 3MCLT/3pp* excited state as the lowest triplet state to achieve an efficient photoinduced ligand exchange. Such an unusual manner offers a clearer understanding of the mechanisms of ligand photodissociation, which can be used to design ruthenium complexes for the applications that require efficient ligand dissociation, such as drug delivery. Furthermore, in order to control CYP activity and to achieve photoactivated CYP inhibition, a series of new Ru(II)-caged CYP inhibitors that effectively liberate CYP inhibitors upon irradiation with low-energy light are described in this thesis. The complexes show strong absorption in the visible range but remain stable in the dark. Photoreleased CYP inhibitors are demonstrated to be capable of undergoing a Type II binding to inactivate CYP activity, and the photo byproducts are non-toxic and well-tolerated by cells. Taken together, this thesis addressed the necessity of the development of Ru(II)-based photocaging groups with high-denticity ancillary ligands for caging nitriles and aromatic heterocycles, and the thesis also established the design and synthesis of Ru(II)-caged CYP inhibitors for controlling CYP activity spatiotemporally with lowenergy ight. Advisors/Committee Members: Jeremy Kodanko.

Subjects/Keywords: Chemistry; Organic Chemistry

Record Details Similar Records Cite « Share

❌

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

APA (6^th Edition):

Li, A. (2018). Design Of Ruthenium(ii) Polypyridyl Complexes For Effectively Caging Nitriles And Aromatic Heterocycles. (Doctoral Dissertation). Wayne State University. Retrieved from https://digitalcommons.wayne.edu/oa_dissertations/2043

Chicago Manual of Style (16^th Edition):

Li, Ao. “Design Of Ruthenium(ii) Polypyridyl Complexes For Effectively Caging Nitriles And Aromatic Heterocycles.” 2018. Doctoral Dissertation, Wayne State University. Accessed February 27, 2021. https://digitalcommons.wayne.edu/oa_dissertations/2043.

MLA Handbook (7^th Edition):

Li, Ao. “Design Of Ruthenium(ii) Polypyridyl Complexes For Effectively Caging Nitriles And Aromatic Heterocycles.” 2018. Web. 27 Feb 2021.

Vancouver:

Li A. Design Of Ruthenium(ii) Polypyridyl Complexes For Effectively Caging Nitriles And Aromatic Heterocycles. [Internet] [Doctoral dissertation]. Wayne State University; 2018. [cited 2021 Feb 27]. Available from: https://digitalcommons.wayne.edu/oa_dissertations/2043.

Council of Science Editors:

Li A. Design Of Ruthenium(ii) Polypyridyl Complexes For Effectively Caging Nitriles And Aromatic Heterocycles. [Doctoral Dissertation]. Wayne State University; 2018. Available from: https://digitalcommons.wayne.edu/oa_dissertations/2043

Florida State University

28. Brassard, Christopher J. Rapid and Selective Syntheses of Trisubstituted -1,2,3-Triazoles Through Copper Mediated Azide Alkyne Cycloaddition.

Degree: PhD, Chemistry and Biochemistry, 2016, Florida State University

URL: http://purl.flvc.org/fsu/fd/FSU_2016SU_Brassard_fsu_0071E_13324-C ;

► This dissertation describes the development of alternative products from the copper-catalyzed azide-alkyne cycloaddition (CuAAC). The first chapter provides an introduction to the CuAAC through the… (more)

▼ This dissertation describes the development of alternative products from the copper-catalyzed azide-alkyne cycloaddition (CuAAC). The first chapter provides an introduction to the CuAAC through the historic timeline of the development of reaction conditions. Finally the current mechanistic understanding and three applications of the commonly used reaction are described. The second chapter describes a method for the preparation of 5-iodo-1,2,3-triazoles directly from organic azides and terminal alkynes. The reaction is mediated by in-situ generated copper(I) catalyst and iodinating agents. The method described is a follow-up of the protocol developed by Dr. Brotherton in 2012. The methodological enhancements of the procedure described in Chapter 2 provides high conversion as well as high iodo/protio selectivity through the reduction in equivalents of alkyne, and employment of [Tri(1-benzyl-1H-1,2,3-triazol-4-yl)methyl]amine (TBTA). Through these improvements the method became more synthetically practical and increased the reaction substrate scope to include unreactive azides and alkynes. Chapter three describes the synthesis of 5,5’-bis(1,2,3-triazole)s (bistriazoles). These compounds have been proposed to be employed as chiral ligands in enantioselective synthesis. Previously reported methods for the synthesis of bistriazoles mainly require decreased reaction temperatures (0-35 °C) and long reaction times (20-48 hours) while applying a limited substrate scope. The method described in Chapter 3 is a simple and rapid process for the synthesis of bistriazoles from organic azides and terminal alkynes under oxidative conditions ( oxygen atmosphere) with a broad substrate scope. The reactions are mediated by copper(II) acetate, and completed within 3 hours, with ≥ 50% isolated yields. TBTA has been employed in the CuAAC to accelerate the formation of 1,2,3-triazoles, in addition TBTA accelerates the formation of bistriazoles. Employing K2CO3 as a basic additive in MeOH or EtOH as the solvent promotes the oxidative reaction that produces the bistriazole at the expense of the 1,2,3-triazole. In Chapter 4 the initial development of 5-alkynyl-1,2,3-triazoles is reported. The previously reported methods require extended reaction times with varying temperature (rt-60 °C) with a limited substrate scope. The method described in Chapter 4 is a simple and rapid process for the synthesis of 5-alkyny-1,2,3-triazoels from organic azides and terminal alkynes under oxidative conditions (oxygen atmosphere) with a developing substrate scope. The reactions are mediated by copper(II) acetate, completed within 3-5 hours, and produce ≥ 50% isolated yields. Employing 1,5-diazolbicyclo[4.3.0]non-5-ene (DBN) as the basic additive in MeOH or EtOH as the solvent promotes the oxidative reaction that produces the 5-alkynyl-1,2,3-triazoles at the expense of the 1,2,3-triazole and 5,5’-bis-(1,2,3-triazole)s. Chapter 5 summarizes the work conducted on modifying the conditions applied to the copper catalyzed azide alkyne cycloaddition (CuAAC).… Advisors/Committee Members: Lei Zhu (professor directing dissertation), Wu-Min Deng (university representative), Gregory B. Dudley (committee member), Mykhailo Shatruk (committee member).

Subjects/Keywords: Chemistry, Organic; Chemistry

Record Details Similar Records Cite « Share

❌

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

APA (6^th Edition):

Brassard, C. J. (2016). Rapid and Selective Syntheses of Trisubstituted -1,2,3-Triazoles Through Copper Mediated Azide Alkyne Cycloaddition. (Doctoral Dissertation). Florida State University. Retrieved from http://purl.flvc.org/fsu/fd/FSU_2016SU_Brassard_fsu_0071E_13324-C ;

Chicago Manual of Style (16^th Edition):

Brassard, Christopher J. “Rapid and Selective Syntheses of Trisubstituted -1,2,3-Triazoles Through Copper Mediated Azide Alkyne Cycloaddition.” 2016. Doctoral Dissertation, Florida State University. Accessed February 27, 2021. http://purl.flvc.org/fsu/fd/FSU_2016SU_Brassard_fsu_0071E_13324-C ;.

MLA Handbook (7^th Edition):

Brassard, Christopher J. “Rapid and Selective Syntheses of Trisubstituted -1,2,3-Triazoles Through Copper Mediated Azide Alkyne Cycloaddition.” 2016. Web. 27 Feb 2021.

Vancouver:

Brassard CJ. Rapid and Selective Syntheses of Trisubstituted -1,2,3-Triazoles Through Copper Mediated Azide Alkyne Cycloaddition. [Internet] [Doctoral dissertation]. Florida State University; 2016. [cited 2021 Feb 27]. Available from: http://purl.flvc.org/fsu/fd/FSU_2016SU_Brassard_fsu_0071E_13324-C ;.

Council of Science Editors:

Brassard CJ. Rapid and Selective Syntheses of Trisubstituted -1,2,3-Triazoles Through Copper Mediated Azide Alkyne Cycloaddition. [Doctoral Dissertation]. Florida State University; 2016. Available from: http://purl.flvc.org/fsu/fd/FSU_2016SU_Brassard_fsu_0071E_13324-C ;

Florida State University

29. Kramer, Nicholas J. James. Reaction Discovery Using Neopentylene-Tethered Coupling Partners: Methodology and Applications of Dienyne Cycloisomerizations.

Degree: PhD, Chemistry and Biochemistry, 2017, Florida State University

URL: http://purl.flvc.org/fsu/fd/FSU_FALL2017_Kramer_fsu_0071E_14204 ;

►

Within the past few decades, metal-catalysis has emerged as a key facet in synthetic organic chemistry, perpetuating a continuous need for the development of methods… (more)

▼

Within the past few decades, metal-catalysis has emerged as a key facet in synthetic organic chemistry, perpetuating a continuous need for the development of methods within this sect of chemistry. In tandem, cycloisomerization reactions of tethered enynes have garnered considerable interest as emphasis on annulation strategies to access polycyclic systems becomes necessary for the generation of important bioactive structures. Driven by both methodological and total synthesis applications, metal-catalyzed cycloisomerizations remain at the forefront of interest for effective atom-economic reactions. We have identified a strategic gap in the methodology of 1,6-enyne cycloisomerizations bearing heteroatom, methylene, and malonate tethers. Herein will be described a method for the [4 + 2] formal Diels-Alder cycloisomerization of neopentylene-tethered dienynes, closing the gap previously mentioned and highlighting a valuable reactivity profile of this new tether. Also demonstrated is significant progress in the Diels-Alder cyclization of electron-deficient dienynes, for which the literature has shown to be relatively unexplored, presumably due to the apparent poor reactivity of these substrates. Further investigation into isolation of the [4 + 2] Diels-Alder products as well as elaboration on the previously published fragmentation/olefination methodology is included in this manuscript. Using these effective annulation strategies developed in our lab, we have sought to gain access to sesquiterpene natural products of particular interest bearing the gem-dimethylcyclopentane, an extension of the indane core. These methods have been employed in a six-step total synthesis of Alcyopterosin A and in the efforts toward the synthesis of Fomajorin D.

A Dissertation submitted to the Department of Chemistry and Biochemistry in partial fulfillment of the requirements for the degree of Doctor of Philosophy.

Fall Semester 2017.

November 14, 2017.

chemistry, methodology, organic, reactions, synthesis

Gregory B. Dudley, Professor Co-Directing Dissertation; James H. Frederich, Professor Co-Directing Dissertation; James M. Fadool, University Representative; Igor V. Alabugin, Committee Member; Michael Shatruk, Committee Member.

Advisors/Committee Members: Gregory B. Dudley (professor co-directing dissertation), James H. Frederich (professor co-directing dissertation), James M. Fadool (university representative), Igor V. Alabugin (committee member), Mykhailo Shatruk (committee member).

Subjects/Keywords: Chemistry, Organic; Chemistry

Record Details Similar Records Cite « Share

❌

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

APA (6^th Edition):

Kramer, N. J. J. (2017). Reaction Discovery Using Neopentylene-Tethered Coupling Partners: Methodology and Applications of Dienyne Cycloisomerizations. (Doctoral Dissertation). Florida State University. Retrieved from http://purl.flvc.org/fsu/fd/FSU_FALL2017_Kramer_fsu_0071E_14204 ;

Chicago Manual of Style (16^th Edition):

Kramer, Nicholas J James. “Reaction Discovery Using Neopentylene-Tethered Coupling Partners: Methodology and Applications of Dienyne Cycloisomerizations.” 2017. Doctoral Dissertation, Florida State University. Accessed February 27, 2021. http://purl.flvc.org/fsu/fd/FSU_FALL2017_Kramer_fsu_0071E_14204 ;.

MLA Handbook (7^th Edition):

Kramer, Nicholas J James. “Reaction Discovery Using Neopentylene-Tethered Coupling Partners: Methodology and Applications of Dienyne Cycloisomerizations.” 2017. Web. 27 Feb 2021.

Vancouver:

Kramer NJJ. Reaction Discovery Using Neopentylene-Tethered Coupling Partners: Methodology and Applications of Dienyne Cycloisomerizations. [Internet] [Doctoral dissertation]. Florida State University; 2017. [cited 2021 Feb 27]. Available from: http://purl.flvc.org/fsu/fd/FSU_FALL2017_Kramer_fsu_0071E_14204 ;.

Council of Science Editors:

Kramer NJJ. Reaction Discovery Using Neopentylene-Tethered Coupling Partners: Methodology and Applications of Dienyne Cycloisomerizations. [Doctoral Dissertation]. Florida State University; 2017. Available from: http://purl.flvc.org/fsu/fd/FSU_FALL2017_Kramer_fsu_0071E_14204 ;

Florida State University

30. Zhang, Xiaoguang. The Study on the Copper(II)-Mediated Azide-Alkyne Cycloaddition Reactions.

Degree: PhD, Chemistry and Biochemistry, 2017, Florida State University

URL: http://purl.flvc.org/fsu/fd/FSU_SUMMER2017_Zhang_fsu_0071E_14063 ;

► The copper(I)-catalyzed azide-alkyne cycloaddition (CuAAC) reaction is an efficient technique for linking two molecules in different applications. Generally, Cu(II) salts were used to generate active… (more)

▼ The copper(I)-catalyzed azide-alkyne cycloaddition (CuAAC) reaction is an efficient technique for linking two molecules in different applications. Generally, Cu(II) salts were used to generate active catalyst Cu(I) by the addition of reducing reagents. In our earlier study, 2-picolyl azide and propargyl alcohol reacted fast in the Cu(OAc)2-assisted azide-alkyne cycloaddition reaction without addition of reducing reagents, which makes the reaction easy to handle and readily to modify the conditions. This dissertation is composed of 5 chapters, which focused on the Cu(II)-mediated azide-alkyne cycloaddition reactions and the reactions derived from the CuAACs. Chapter 1 is the introduction to the development of the CuAAC reactions. The mechanistic study on CuAAC reactions from the computational aspect and the experimental aspect were reviewed to understand and describe the proposed mechanism of the CuAAC reactions. The impact of components, such as solvent, copper salts, ligands, and so on, were summarized in this chapter. At the end of this chapter, the unresolved problems were put forwarded for improving the efficiency and the flexibility of CuAACs in future applications. Chapter 2 focuses on the reactivity of the alkynes in CuAAC reactions. Though the alkyne is an important component in CuAACs, the study on the reactivity of alkynes has not been reported much. It brings difficulties in understanding the mechanism as well as in the application of the alkynes. In this chapter, various alkynes were designed and compared under different conditions through 1H NMR monitoring experiments. The behavior of the alkyne were analyzed under conditions: Cu(II), Cu(I), and existence of ligand TBTA. Through ranking the reactivity of alkynes under different conditions, the factors that contribute to their reactivity were analyzed and discussed, which offers a guidance for practical purpose. Chapter 3 focuses on a special class of organic azides. These azides have ability to chelate copper ions and displayed high reactivity in Cu(II)-mediated azide-alkyne cycloaddition reactions. The mechanism of the reaction has been proposed, but the impact from the structure of azides remained unclear. In this chapter, the binding affinity of azides was measured via the isothermal calorimetry (ITC) method for evaluating the chelation effect on the reactivity of the azides. The N-heterocyclic (NHC) carbene stabilized copper triazolide was employed to study the impact of azides in the cycloaddition step and the protonation step. Moreover, the dinucleared copper complex involves Cu(I) and Cu(II) were compared using carbene stabilized copper triazolide. Chapter 4 focuses on the synthesis of 5,5’-bis-1,2,3-triazoles. Bistriazoles are oxidative dimers generated in CuAAC reactions. The compounds were noticed as side products in CuAAC reactions by Sharpless and co-workers, but they did not report it. Burgess first reported the compound as major product under basic conditions. In the existing protocols for synthesizing bistriazoles, the long reaction time… Advisors/Committee Members: Lei (Professor of chemistry) Zhu (professor directing dissertation), Peter G. Fajer (university representative), Igor V. (Professor) Alabugin (committee member), Mykhailo Shatruk (committee member).

Subjects/Keywords: Chemistry; Chemistry, Organic

Record Details Similar Records Cite « Share

❌

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

APA (6^th Edition):

Zhang, X. (2017). The Study on the Copper(II)-Mediated Azide-Alkyne Cycloaddition Reactions. (Doctoral Dissertation). Florida State University. Retrieved from http://purl.flvc.org/fsu/fd/FSU_SUMMER2017_Zhang_fsu_0071E_14063 ;

Chicago Manual of Style (16^th Edition):

Zhang, Xiaoguang. “The Study on the Copper(II)-Mediated Azide-Alkyne Cycloaddition Reactions.” 2017. Doctoral Dissertation, Florida State University. Accessed February 27, 2021. http://purl.flvc.org/fsu/fd/FSU_SUMMER2017_Zhang_fsu_0071E_14063 ;.

MLA Handbook (7^th Edition):

Zhang, Xiaoguang. “The Study on the Copper(II)-Mediated Azide-Alkyne Cycloaddition Reactions.” 2017. Web. 27 Feb 2021.

Vancouver:

Zhang X. The Study on the Copper(II)-Mediated Azide-Alkyne Cycloaddition Reactions. [Internet] [Doctoral dissertation]. Florida State University; 2017. [cited 2021 Feb 27]. Available from: http://purl.flvc.org/fsu/fd/FSU_SUMMER2017_Zhang_fsu_0071E_14063 ;.

Council of Science Editors:

Zhang X. The Study on the Copper(II)-Mediated Azide-Alkyne Cycloaddition Reactions. [Doctoral Dissertation]. Florida State University; 2017. Available from: http://purl.flvc.org/fsu/fd/FSU_SUMMER2017_Zhang_fsu_0071E_14063 ;

Open Access Theses and Dissertations