The tandem Ugi-Smiles Intramolecular Diels-Alder (US-IMDA) reaction provides efficient assembly of diastereomeric epoxyisoindoline products through a one-pot multicomponent coupling. A library of related compounds can be assembled by variation of reaction components and through modification of the resulting epoxyisoindoline scaffolds. This work aimed to address three areas of interest for the further development of these products: examination of ease of epimerization, reduction of nitro-substituents, and use of polymer-supported reagents. Ease of epimerization for these diastereomers is dependent on epoxyisoindoline substitution patterns, although all epimerizations require forcing conditions. Selective reduction to convert the nitro group on US-IMDA products to an amino functional group provided moederate yields (33%–78%) of isolated amine products. Use of resin-supported isocyanide components have shown limited utility in this reaction. Current efforts are focused on epimerization of further US/US-IMDA reaction products, ketone-based analogs of the Ugi-Smiles coupling, and use of resin-supported isocyanides to simplify product isolation and purification processes.
|Commitee:||Jones, Myron, Lu, Yun|
|School:||Southern Illinois University at Edwardsville|
|School Location:||United States -- Illinois|
|Source:||MAI 56/06M(E), Masters Abstracts International|
|Subjects:||Chemistry, Organic chemistry|
|Keywords:||Epimerization, Polymer-supported synthesis, Reactions, Reduction, Synthesis, Ugi-Smiles|
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