Phenol Ugi-Smiles Systems: Strategies for the Multicomponent N-Arylation of Primary Amines with Isocyanides, Aldehydes, and Phenols

• Published in: Angewandte Chemie (International ed.) Vol. 44; no. 48; pp. 7961 - 7964
• Main Authors: El Kaïm, Laurent, Grimaud, Laurence, Oble, Julie
• Format: Journal Article
• Language: English
• Published: Weinheim WILEY-VCH Verlag 09.12.2005; WILEY‐VCH Verlag; Wiley
• Subjects: amines; arylation; Chemistry; Chemistry, Multidisciplinary; multicomponent reaction; phenols; Physical Sciences; rearrangement; Science & Technology; phenols; amines; ISONITRILE; CHEMISTRY; multicomponent reaction; rearrangement; arylation

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...