Dissertation/Thesis Abstract

Investigation of the Scope of the Dual Ugi-Smiles Diels-Alder Process
by Mason, Katelynn, M.S., Southern Illinois University at Edwardsville, 2015, 119; 1600539
Abstract (Summary)

A multicomponent coupling reaction (MCR) is a highly efficient process that is capable of producing diversely functionalized molecules. These reactions can efficiently form several new bonds and generate stereocenters in a one-pot process. While there are many variations of MCRs, isocyanide-based MCRs (IMCRs) are widely utilized in the pharmaceutical industry due to their apparent capability to produce peptide-like products. One specific example of an IMCR is the Ugi-Smiles reaction which combines an aldehyde, an amine, a phenol, and an isocyanide to yield α-aminoacyl amide derivatives. IMCRs can also be used in combination with another reaction to produce more drug-like scaffolds. For example, a Diels-Alder cyclization can occur immediately following an MCR to create a more complex, cyclic product.

This work describes a novel dual Ugi-Smiles Diels-Alder process. The Ugi-Smiles reaction occurs along with an intramolecular Diels-Alder with furan (IMDAF) cyclization to prepare epoxyisoindolines, heterocyclic compounds that are precursors to biologically active molecules. Through evaluation of variations in reaction components, a small library of compounds were prepared, providing insight into the scope of these reactions and the stereochemistry of the products.

Indexing (document details)
Advisor: Luesse, Sarah
Commitee: De Meo, Cristina, O'Brien, Leah, Wei, Chin-Chuan
School: Southern Illinois University at Edwardsville
Department: Chemistry
School Location: United States -- Illinois
Source: MAI 55/02M(E), Masters Abstracts International
Source Type: DISSERTATION
Subjects: Organic chemistry
Keywords:
Publication Number: 1600539
ISBN: 9781339094717
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