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.elkaim
ensta.fr,
laurence.grimaudensta.fr
L. El Kaim, L. Grimaud, J. Oble, Angew. Chem. Int. Ed., 2005, 44, 7961-7964.
DOI: 10.1002/anie.200502636
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
