Phenol Ugi-Smiles systems: Strategies for the multicomponent N-arylation of primary amines with isocyanides, aldehydes, and phenols

(Chemical Equation Presented) A Smiles rearrangement is the key step in the efficient coupling of primary amines with isocyanides, carbonyl compounds, and electron-deficient substituted phenols to form N-aryl amines (see picture). The presence of a nitro or ester group on the resulting adduct allows applications in heterocyclic synthesis.