Smiles rearrangements in Ugi- and Passerini-type couplings: new multicomponent access to O- and N-arylamides.

Laurent El Kaïm, Marie Gizolme, Laurence Grimaud, Julie Oble

Index: J. Org. Chem. 72 , 4169, (2007)

Full Text: HTML

Abstract

The use of Smiles rearrangement in Ugi- and Passerini-type couplings with electron-deficient phenols allows very straightforward multicomponent formation of O-aryl- and N-arylamides. Best yields were observed with the highly activated o- and p-nitrophenols, salicylic derivatives giving adducts in lower yields. The scope of these new reactions is further increased by the successful couplings of heterocyclic phenols such as hydroxypyridines and hydroxypyrimidines.