The Passerini-Smiles reaction is the efficient three-component coupling reaction of a phenol, aldehyde, and isocyanide. To extend the utility of this process for tandem reaction development, efforts focused on the use of conjugated, heterocyclic aldehydes to generate novel a-acyloxy amide products. These aldehydes broaden the scope of the known reaction by providing structural features inclined to cyclization events. Synthesis of allyl-substituted nitrophenols, through a two-step process involving allylation and Claisen rearrangement, provided single components with two sites of reactivity for preliminary efforts towards development of a tandem Passerini-Smiles cyclization process. The goal of this work is the production of a small library of compounds with a wide variety of molecular diversity, attractive for drug discovery efforts.

Examining the use of conjugated, heterocyclic aldehydes in the Passerini-Smiles reaction

247th National Meeting (2014)

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