BETA-LITHIATIONS OF CARBOXAMIDES - SYNTHESIS OF BETA-SUBSTITUTED-ALPHA,BETA-UNSATURATED AMIDES

Authors
KATRITZKY AR SZAJDA M LAM JN
Citation
Ar. Katritzky et al., BETA-LITHIATIONS OF CARBOXAMIDES - SYNTHESIS OF BETA-SUBSTITUTED-ALPHA,BETA-UNSATURATED AMIDES, Journal of heterocyclic chemistry, 30(5), 1993, pp. 1261-1265
Citations number
27
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Journal of heterocyclic chemistry → ACNP
ISSN journal
0022152X
Volume
30
Issue
5
Year of publication
1993
Pages
1261 - 1265
Database
ISI
SICI code
0022-152X(1993)30:5<1261:BOC-SO>2.0.ZU;2-W
Abstract
-Methyl-2-methyl-3-(benzotriazol-1-yl)propanamide, on treatment with b utyllithium forms a dianion which on treatment with alkyl and benzyl h alides, aldehydes and ketones affords monosubstituted products; with e thyl p-toluate, a lactam is formed. The alkylated derivatives eliminat e benzotriazole in the presence of base to afford trisubstituted alpha ,beta-unsaturated amides.