Dissertation/Thesis Abstract

Exploration of an Oxy-Michael Ugi-Smiles Process
by Zangi, Maryam, M.S., Southern Illinois University at Edwardsville, 2018, 68; 10844310
Abstract (Summary)

Multicomponent coupling reactions (MCRs) are efficient methods used in the synthesis of biologically-active complex molecules. In MCRs, three or more starting materials react in a single reaction process to assemble a desired product scaffold. The ability to access diverse structural motifs through a one-pot process, along with the generation of new bonds and stereocenters, makes MCR strategies important tools in drug discovery efforts. Specifically, efforts have focused on strategies that combine MCRs with combinatorial chemistry methods to rapidly prepare diverse chemical libraries.

The Ugi-Smiles reaction, a four-component coupling (4CC), is an MCR in which an aldehyde, phenol, amine, and isocyanide are combined through a one-pot process to form a peptide-like amide structure. Previous efforts in the Luesse lab towards variation of the Ugi-Smiles intramolecular Diels-Alder (US-IMDA) reaction led to attempts to incorporate an α,β-unsaturated aldehyde as a reagent. These studies led to the discovery of an unexpected Ugi-Smiles modification, a five-component Oxy-Michael Ugi-Smiles (OM-US) coupling.

This work describes the expansion of the OM-US process, through examination of different reaction conditions and exploration of aldehyde and isocyanide component variations. This study had led to the preparation of a small library of compounds.

Indexing (document details)
Advisor: Luesse, Sarah
Commitee: De Meo, Cristina, Dixon, Robert, Shaw, Michael
School: Southern Illinois University at Edwardsville
Department: Chemistry
School Location: United States -- Illinois
Source: MAI 58/04M(E), Masters Abstracts International
Subjects: Chemistry, Organic chemistry
Publication Number: 10844310
ISBN: 978-0-438-80171-4
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