Dissertation/Thesis Abstract

Effect of Component Variation on the Passerini-Smiles Reaction
by Summers, Chante, M.S., Southern Illinois University at Edwardsville, 2016, 105; 10125668
Abstract (Summary)

A multicomponent coupling reaction (MCR) is a powerful transformation, combining three or more starting materials to form several new bonds in a one-pot process that efficiently affords highly functionalized molecular scaffolds. The Passerini-Smiles reaction is an isocyanide-based multicomponent coupling reaction (IMCR) that combines an electron-deficient phenol, aldehyde, and isocyanide to produce an α-acyloxy amide. Reactions like this provide methods to construct diverse families of compounds, and are useful for the synthesis of biologically-relevant complex molecules.

Herein we report the discovery of novel, Passerini-Smiles acyl adduct isomers when furaldehyde derivatives are used as a reaction component. Our goals focus on evaluation of the functional group tolerance for this reaction, and gaining a better understanding of the reaction scope and mechanism. Application of allyl-substituted nitrophenols in the Passerini Smiles reaction provides rearranged acyl adducts. This reaction was further developed through optimization studies and functional group variation.

Indexing (document details)
Advisor: Luesse, Sarah
Commitee: Dixon, Robert, Miller, Lynne, Wei, Chin-Chuan
School: Southern Illinois University at Edwardsville
Department: Chemistry
School Location: United States -- Illinois
Source: MAI 55/05M(E), Masters Abstracts International
Subjects: Organic chemistry
Keywords: Allyl substituted nitrophenols, Aryl adducts, Isocyanide-based multicomponent coupling reaction, Passerini-smiles
Publication Number: 10125668
ISBN: 978-1-339-83740-6
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