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

The Journal of organic chemistry (2007-04-26)
Laurent El Kaïm, Marie Gizolme, Laurence Grimaud, Julie Oble
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.

MATERIALS
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Product Description

Sigma-Aldrich
Benzyl isocyanide, 98%