Chemistry Commons^™

The Effect Of Variation Of N-Substituents On Oxidopyridinium Ions In (4+3) Cycloadditions, Zahria Patrick, Madison Clark

Undergraduate Research Symposium

The aim of this research project is to expand the scope of 4 + 3 cycloadduct chemistry by varying functional groups attached to the prerequisite oxidopyridinium ion for each respective cycloadduct product. While N-substitution of the pyridinium precursor is known to proceed smoothly if alkylated by a lone methyl group, we evaluated the effect a larger alkyl group would have on the overall yield of the 4 + 3 cycloadduct product.

Isobutyl triflate, generated from the known reaction between isobutyl alcohol and triflic anhydride, was reacted with ethyl 5-hydroxy-nicotinate to generate the respective N-isobutyl oxidopyridinium ion in quantitative …

Synthesis Of Functionalized Tetrahydropyridines By Sncl4-Mediated [4+2] Cycloaddition Between Donor–Acceptor Cyclobutanes And Nitriles, David Tong, Jackie Wu, Nathan Bazinski, Donghyun Koo, Naresh Vemula, Brian Pagenkopf

Chemistry Publications

Cycloadditions of strained carbocycles promoted by Lewis acids are powerful methods to construct heterocyclic frameworks. In fact, the formal [3+2] cycloadditions of donor-acceptor (DA) cyclopropanes with nitriles has seen particular success in synthesis. In this work, we report on the first [4+2] cycloaddition of nitriles with DA cyclobutanes via Lewis acid activation. Tetrahydropyridine derivatives were obtained in up to 91% yield from various aryl activated cyclobutane diesters and aliphatic or aromatic nitriles.

Synthesis And Characterization Of Amide Linked Triazolyl Glycolipids As Molecular Hydrogelators And Organogelators, Guijun Wang, Anji Chen, Hari P. R. Mangunuru, Jayasudhan Reddy Yerabolu

Chemistry & Biochemistry Faculty Publications

Carbohydrate based small molecular gelators are important classes of compounds which can form useful soft materials with many practical applications. Although many different types of effective gelators have been reported, the rational design of a molecular hydrogelator is still challenging. In this research, we combined the structural features of two classes of monosaccharide based molecular gelators and obtained a new class of glycolipids that can function as molecular gelators. These new compounds were synthesized by introducing a triazole functional group to a protected 2-glucosamine through Cu(i) catalyzed azide/alkyne cycloaddition reaction (CuAAC). A series of eighteen new glycolipids containing 4,6-O …

Progress Toward The Synthesis Of Novel Heterocyclic Compounds: Via Diels-Alder Reactions, Including Microwave Promotion, Douglas Armstrong, Kristen Richey

Faculty Scholarship – Chemistry

Benzofurazan 1 was reacted with 4,5-diphenyl-1,3-dioxol-2-one 2 in refluxing toluene. No reaction (NR) was detected by TLC analysis, as indicated below. It was decided that a higher-boiling solvent should be used. Accordingly, in the next trial, the same two reactants were used but this time with refluxing mesitylene as the solvent. A TLC analysis indicated a product was formed, but both reactants were still present in the reaction mixture. Another experiment with these conditions was run with a 30% excess of benzofurazan, to try to get all of the 4,5-diphenyl-1,3-dioxol-2-onetoreact. However, a TLC analysis of this reaction mixture showed the …

One-Pot Three-Step Thioconjugate Addition-Oxidation-Diels–Alder Reactions Of Ethyl Propiolate, C. Wade Downey, Smaranda Craciun, Christina A. Vivelo, Ana M. Neferu, Carly J. Mueller, Stephanie Corsi

Chemistry Faculty Publications

Ethyl propiolate undergoes one-pot three-step thioconjugate addition-oxidation-Diels–Alder cycloaddition when treated with a variety of thiols in the presence of catalytic base, meta-chloroperbenzoic acid, lithium perchlorate, and cyclopentadiene. The reaction of S‑aryl thiols is catalyzed by trialkylamines, and the reaction of aliphatic thiols requires catalytic alkoxide base. Yields of the major diastereomer of the conveniently functionalized bicyclic products range from 47 to 81% depending upon the thiol reactant, which compares favorably to yields observed when the entire synthesis is performed step by step.

Reactivity Of Acyclic (Pentadienyl)Iron(1+) Cations: Synthetic Studies Directed Toward The Frondosins, Do W. Lee, Rajesh K. Pandey, Sergey Lindeman, William Donaldson

Chemistry Faculty Research and Publications

A short, 4-step route to the scaffold of frondosin A and B is reported. The [1-methoxycarbonyl-5-(2′,5′-dimethoxyphenyl)pentadienyl]Fe(CO)₃⁺ cation was prepared in two steps from (methyl 6-oxo-2,4-hexadienoate)Fe(CO)₃. Reaction of this cation with isopropenyl Grignard or cyclohexenyllithium reagents affords (2-alkenyl-5-aryl-1-methoxycarbonyl-3-pentene-1,5-diyl)Fe(CO)₃ along with other addition products. Oxidative decomplexation of these (pentenediyl)iron complexes, utilizing CuCl₂, affords 6-aryl-3-methoxycarbonyl-1,4-cycloheptadienes via the presumed intermediacy of a cis-divinylcyclopropane.

Synthesis Of Hydroxy- And Polyhydroxy-Substituted 1,3-Diaminocyclohexanes, Anobick Sar, Sergey Lindeman, William Donaldson

Chemistry Faculty Research and Publications

The synthesis of hydroxy-trans-1,3-diaminocyclo­hexanes based on nitroso-Diels-Alder cycloaddition of (cyclohexadienyl)phthalimide is reported.