BENZOTRIAZOLE-ASSISTED PREPARATIONS OF 2-(SUBSTITUTED AMINO)PYRIDIMESAND PYRID-2 ONES

Authors
KATRITZKY AR BELYAKOV SA SOROCHINSKY AE HENDERSON SA CHEN J
Citation
Ar. Katritzky et al., BENZOTRIAZOLE-ASSISTED PREPARATIONS OF 2-(SUBSTITUTED AMINO)PYRIDIMESAND PYRID-2 ONES, Journal of organic chemistry, 62(18), 1997, pp. 6210-6214
Citations number
19
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Journal of organic chemistry → ACNP
ISSN journal
00223263
Volume
62
Issue
18
Year of publication
1997
Pages
6210 - 6214
Database
ISI
SICI code
0022-3263(1997)62:18<6210:BPO2A>2.0.ZU;2-9
Abstract
Base-promoted reactions of benzotriazolyl-containing acetic acid deriv atives, 2-(benzotriazol-1-yl)acetonitrile (7a), 2-(benzotriazol-1-yl)a cetamide (7b), and (+/-)-2-(benzotriazol-1-yl)propionamide (7c), with alpha,beta-unsaturated ketones 8 give efficient and regioselective acc ess to previously difficult to attain 3-unsubstituted pyridine derivat ives: the 2-(substituted amino)pyridines 14a-k and the 4,6-substituted pyrid-2-ones 15a-h. The pyridine rings result from tandem [3 + 3] ann ulations involving a Michael addition followed by cyclization.