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

2007; American Chemical Society; Volume: 72; Issue: 11 Linguagem: Inglês

10.1021/jo070202e

1520-6904

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

Chemical Synthesis and Analysis

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.