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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Published in | Journal of organic chemistry Vol. 72; no. 11; pp. 4169 - 4180 |
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Main Authors | , , , |
Format | Journal Article |
Language | English |
Published |
WASHINGTON
American Chemical Society
25.05.2007
Amer Chemical Soc |
Subjects | |
Online Access | Get full text |
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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. |
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Bibliography: | ark:/67375/TPS-JM3LSWXS-8 istex:A7252898628B57591E5747D760FD9DA709608760 ObjectType-Article-1 SourceType-Scholarly Journals-1 ObjectType-Feature-2 content type line 23 |
ISSN: | 0022-3263 1520-6904 |
DOI: | 10.1021/jo070202e |