Undergraduate Honors Thesis Projects

Date of Award

2015

Document Type

Honors Paper

Degree Name

Chemistry-BS

Department

Chemistry

Advisor

Dr. Robin Grote

First Committee Member

Dr. Jerry Jenkins

Second Committee Member

Dr. Karen Steigman

Keywords

Transition Metal Catalysis, Gold-Catalyzed, Intermolecular Cyclization, Palladium-Catalyzed, Heterocycle, Suzuki Cross-Coupling

Subject Categories

Organic Chemistry

Abstract

Two methods of transition metal catalysis were investigated as a means to synthesize biologically interesting heterocyclic molecules. The gold-catalyzed intermolecular cyclization of allenes and 1,3-dipoles was first explored. An allene, ethyl-3-hexyl-3,4-pentadienoate was subjected to a combination of one of five 1,3-dipoles ((Z)-N-benzylidenemethanamine oxide, 1-benzylidene-3-oxopyrazolidin-1-ium-2-ide, (Z)-N-benzylidenebenzenamine oxide, (E)-N-benzylidenebenylamine, and (E)-N-Benzylidene-4-methoxybenzenamine) and one of three gold catalysts (1,3-bis(2,6-di-isopropylphenyl)imidazole-2-ylidenegold(I)chloride, chlorotriphenyl-phosphinegold(I), and gold(III) chloride). No heterocyclic product resulted from these catalytic reactions. The palladium-catalyzed Suzuki cross-coupling reaction of a 1,3,4-oxadiazole (3-(5-(4-(bromo)phenyl)-1,3,4-oxadiazol-2-yl)pyrazine-2-amine) with phenyl boronic pinacol ester was then explored, varying whether the 1,3,4-oxadiazole was unprotected or BOC-protected. BOC-protected 3-(5-(4-(bromo)phenyl)-1,3,4-oxadiazol-2-yl)pyrazine-2-amine was capable of cross-coupling, while the unprotected derivative was not able. Upon employing a wide variety of boronic acids and boronic esters in the cross-coupling reactions, the products will then be able to be tested for biological activity.

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