Dissertation/Thesis Abstract

Exploration of a Tandem Diels-Alder Ugi-Smiles Reaction
by Richey, Bree, M.S., Southern Illinois University at Edwardsville, 2014, 84; 1560387
Abstract (Summary)

A multicomponent coupling reaction (MCR) is a very efficient synthetic method, capable of forming several new bonds in a one-pot process to afford highly functionalized molecules. An Ugi-Smiles reaction is an isocyanide-based multicomponent coupling reaction (IMCR) that combines an aldehyde, amine, isocyanide, and phenol. When an IMCR produces a product that can directly undergo a second reaction, the resulting tandem process provides rapid access to complex, drug-like compounds. The combination of an Ugi-Smiles MCR with an intramolecular Diels-Alder with furan (IMDAF) cyclization process leads to formation of heterocyclic precursors to biologically active molecules.

Herein we describe the discovery of a novel, tandem IMDAF/Ugi-Smiles tandem process. Our goals focus on development of this process to gain a better understanding of the scope, mechanism, and issues of stereochemistry. Reaction optimization studies and functional group variation for components provide insight for application to the synthesis of a small library of epoxyisoindolines, precursors of biologically-active isoindolines. Additional studies laid a strong foundation towards understanding the mechanism and stereochemical results of this novel tandem process.

Indexing (document details)
Advisor: Luesse, Sarah B.
Commitee: DeMeo, Cristina, Lu, Yun
School: Southern Illinois University at Edwardsville
Department: Chemistry
School Location: United States -- Illinois
Source: MAI 53/03M(E), Masters Abstracts International
Subjects: Organic chemistry
Publication Number: 1560387
ISBN: 978-1-321-02807-2
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