SYNTHESIS OF HETEROCYCLIC-SYSTEMS WITH CARBOHYDRATE FRAGMENT .2. STEREOSELECTIVE SYNTHESIS OF TETRAHYDROPYRIDONES BY REACTION OF LEVOGLUCOSENONE WITH AMIDES OF ALPHA-METHYLENE-ACTIVE ACIDS

Authors
SAMET AV KISLYI VP CHERNYSHOVA NB REZNIKOV DN UGRAK BI SEMENOV VV
Citation
Av. Samet et al., SYNTHESIS OF HETEROCYCLIC-SYSTEMS WITH CARBOHYDRATE FRAGMENT .2. STEREOSELECTIVE SYNTHESIS OF TETRAHYDROPYRIDONES BY REACTION OF LEVOGLUCOSENONE WITH AMIDES OF ALPHA-METHYLENE-ACTIVE ACIDS, Russian chemical bulletin, 45(2), 1996, pp. 393-398
Citations number
15
Categorie Soggetti
Chemistry
Journal title
Russian chemical bulletin → ACNP
ISSN journal
10665285
Volume
45
Issue
2
Year of publication
1996
Pages
393 - 398
Database
ISI
SICI code
1066-5285(1996)45:2<393:SOHWCF>2.0.ZU;2-O
Abstract
The reactions of levoglucosenone with amides of several alpha-nitrocar boxylic acids and acetoacetic acid result in tetrahydropyridones fused with a carbohydrate fragment. In the case of acetoacetic acid amides, mixtures of keto and enol tautomers were obtained. The stereochemistr y of cyclization is discussed in detail.