Dissertation/Thesis Abstract

Formation of Novel Oxatricycles via Ugi-Smiles Diels-Alder Cascade
by Meyers, Michael S., M.S., Southern Illinois University at Edwardsville, 2016, 138; 10159227
Abstract (Summary)

With the endeavor to find new efficient synthetic methods to rapidly access diverse molecular structures, great effort has been given to developing new multicomponent coupling reactions (MCR). These reactions are cascade processes in which several reagents are assembled together in a single reaction process. During this process, several new bonds, sterocenters and key privileged structural motifs are generated. For this reason, MCRs have found wide use in drug lead discovery efforts. A specialized type of MCR involving the use of isocyanide known as isocyanide based MCRs (IMCRs) generate peptide-like structural elements key to pharmaceutical development. The Ugi-Smiles MCR is one in which an isocyanide, aldehyde, phenol and amine are assembled to form α-aminoacyl amide derivatives. These reactions have shown to allow for rapid construction of vast compound libraries due to their versatility as well as there ability to construct structures that can readily undergo further molecular transformations.

The work presented details further work in the exploration of a newly developed novel Ugi-Smiles Diels-Alder tandem cascade process. In this MCR variant, α,β-unsaturated heterocyclic 2-furaldehyde is utilized in order couple the Ugi-Smiles reaction with an intramolecular Diels-Alder process. This process allows for rapid access to the preparation of epoxyisoindoline structures which have been proven to be valuable precursors to biologically active compounds. Exploration into the diverse effects of coupling component variations, key understanding of this new novel process was gained as well as a small library of compounds generated.

Indexing (document details)
Advisor: Luesse, Sarah B.
Commitee: DeMeo, Christina, Sumita, Mina
School: Southern Illinois University at Edwardsville
Department: Chemistry
School Location: United States -- Illinois
Source: MAI 56/01M(E), Masters Abstracts International
Subjects: Pharmacology, Molecular chemistry, Chemistry
Publication Number: 10159227
ISBN: 978-1-369-14218-1
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