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Communication
Phenol Ugi–Smiles Systems: Strategies for the Multicomponent N-Arylation of Primary Amines with Isocyanides, Aldehydes, and Phenols
Article first published online: 15 NOV 2005
DOI: 10.1002/anie.200502636
Copyright © 2005 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
Additional Information
How to Cite
El Kaïm, L., Grimaud, L. and Oble, J. (2005), Phenol Ugi–Smiles Systems: Strategies for the Multicomponent N-Arylation of Primary Amines with Isocyanides, Aldehydes, and Phenols. Angewandte Chemie International Edition, 44: 7961–7964. doi: 10.1002/anie.200502636
Publication History
- Issue published online: 8 DEC 2005
- Article first published online: 15 NOV 2005
- Manuscript Received: 27 JUL 2005
Keywords:
- amines;
- arylation;
- multicomponent reaction;
- phenols;
- rearrangement
Graphical Abstract
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.