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Dissertation/Thesis Abstract

Examination of Amine and Thiol Variation in Tandem Michael Ugi-Smiles Processes
by Robinson, Ashley, M.S., Southern Illinois University at Edwardsville, 2020, 61; 28030455
Abstract (Summary)

Multicomponent coupling reactions (MCRs) are high-conversion, one-pot processes that combine three or more reagents to form numerous new bonds in a product scaffold. MCRs are extremely atom-efficient and have the ability to significantly shorten the synthetic scheme of many natural products with structures useful in pharmaceutical industry and drug development. It is common that large libraries of similarly structured compounds must be synthesized in order to evaluate potential drug candidates. With the use of MCRs in synthetic pathways, the number of reaction and purification steps can be reduced, all while assembling diverse products.

A specific MCR of interest is the four-component coupling Ugi-Smiles reaction, which combines an aldehyde, amine, phenol, and isocyanide. While studying the use of α,β-unsaturated aldehydes in this reaction, a novel five-component coupling reaction was discovered and identified as a dual oxy-Michael Ugi-Smiles process. In this coupling reaction, the methanol solvent acts a nucleophile and adds to the conjugated portion of the aldehyde. This work describes studies focused on the investigation of various amine components, as well as introducing non-alcoholic solvents as the fifth reaction component in order to introduce more diversity into the product scaffold.

Indexing (document details)
Advisor: Luesse, Sarah B.
Commitee: De Meo, Cristina, Voss, Eric J.
School: Southern Illinois University at Edwardsville
Department: Chemistry
School Location: United States -- Illinois
Source: MAI 82/3(E), Masters Abstracts International
Subjects: Chemistry, Organic chemistry
Keywords: Multicomponent coupling reactions
Publication Number: 28030455
ISBN: 9798672113432
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