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

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 lo...

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Bibliographic Details
Published in:Journal of organic chemistry 2007-05, Vol.72 (11), p.4169-4180
Main Authors: El Kaïm, Laurent, Gizolme, Marie, Grimaud, Laurence, Oble, Julie
Format: Article
Language:English
Subjects:
Amides - chemical synthesis
Catalysis
Cyclization
Heterocyclic Compounds - chemical synthesis
Molecular Structure
Nitrophenols - chemistry
Pyridines - chemistry
Stereoisomerism
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Summary: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.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo070202e