Methods that efficiently assemble complex heterocyclic scaffolds as building blocks for novel, biologically-active compounds are in demand. The Passerini-Smiles reaction is a three-component coupling of an aldehyde, phenol, and isocyanide to generate an α-acyloxyamide. Use of 5-substituted-2-furaldehyde components led to observation of an unexpected post-condensation rearrangement process. Recent efforts have focused on the rearrangement pathway through use of 5-methyl-2-furaldehyde or 4,5-dimethyl-2-furaldehyde and catalytic base variations. Preliminary results have shown increased yields for couplings that utilized 5-bromo-2-nitrophenol as a reaction component.

Effect of component variation on Passerini-Smiles couplings

2019 Spring National Meeting

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