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

Laurent El Kaïm*, Laurence Grimaud*, Julie Oble

*Laboratoire de Chimie Organique, UMR CNRS 7652, Ecole Nationale Supérieure des Techniques Avancées, 32 Bd Victor, 75015, Email: laurent.elkaimensta.fr, laurence.grimaudensta.fr

L. El Kaim, L. Grimaud, J. Oble, Angew. Chem. Int. Ed., 2005, 44, 7961-7964.

DOI: 10.1002/anie.200502636 (free Supporting Information)


Abstract

A novel and very efficient four-component reaction from readily available substrates has been developed. In the Ugi reaction, equilibria between primary amines, isocyanides, carbonyl compounds and carboxylic acids are displaced by a final irreversible Mumm-type rearrangement. The carboxylic acid can be replaced by o-nitrophenol, p-nitrophenol, or salicylate. The irreversible last step is then a Smiles rearrangement.

see article for more examples

see article for more reactions


proposed mechanism for the phenol Ugi-Smiles reaction



O-Arylative Passerini Reactions

L. El Kaim, M. Gizolme, L. Grimaud, Org. Lett., 2006, 8, 5021-5023.

Smiles Rearrangements in Ugi- and Passerini-Type Couplings: New Multicomponent Access to O- and N-Arylamides

L. El Kaim, M. Gizolme, L. Grimaud, J. Oble, J. Org. Chem., 2006, 71, 4169-4180. DOI: 10.1021/jo070202e


Key Words

amines, arylation, multicomponent reaction, phenols, rearrangement, Ugi reaction, Smiles reaction


ID: J06-Y2005-2060