The Passerini-Smiles reaction is the efficient three-component coupling reaction of a phenol, aldehyde, and isocyanide. Recent efforts have focused on the use of conjugated, heterocyclic aldehydes and allyl-substituted nitrophenols to incorporate additional functional groups for use in tandem reaction development. Synthesis of allyl-substituted nitrophenols, through a two-step process involving allylation and Claisen rearrangement, provided components with two sites of reactivity. Preliminary efforts towards development of a tandem Passerini-Smiles cyclization process provided a small library of functionally-diverse compounds, attractive for drug discovery efforts.

Allyl-substituted nitrophenols in the Passerini-Smiles reaction

249th National Meeting (2015)

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