The Passerini-Smiles reaction is an efficient one-pot method used to assemble an a-acyloxyamide scaffold from a phenol, an aldehyde, and an isocyanide. Conjugated, hetereocyclic aldehydes, such as 2-furaldehyde, are successful reaction components. However, substituents on the furan ring influence the observed products, as 5-substituted-2-furaldehyde derived Passerini-Smiles products undergo rearrangement. Recent studies are focused on exploring the rearrangement process through variation in phenol and aldehyde substitution.<br/>

Investigation of substituted furaldehydes in the Passerini-Smiles reaction

253rd National Meeting (2017)

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