Multicomponent coupling reactions (MCRs) are efficient methods for generating potential pharmaceutical scaffolds. The Ugi-Smiles reaction is a well-established four-component coupling of a phenol, amine, aldehyde, and isocyanide that forms a highly-functionalized amide. Employing 2-furaldehyde and allylamine in this reaction resulted in a tandem Ugi-Smiles Diels-Alder (US-IMDA) process to generate an epoxyisoindoline. Studies have been directed at assessing substrate tolerance of the amine and phenol components to gain further understanding of the scope of this novel reaction and to prepare a small library of highly functionalized compounds.

Tandem Ugi-Smiles Diels-Alder reactions: Evaluation of substrate scope

253rd National Meeting (2017)

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