SYNTHESIS OF FUNCTIONALIZED 3,4-DIHYDRO-2H-PYRANS BY HETERO - DIELS-ALDER REACTION OF AN ENAMINOKETONE WITH ENOL ETHERS

Authors
BOGDANOWICZSZWED K PALASZ A
Citation
K. Bogdanowiczszwed et A. Palasz, SYNTHESIS OF FUNCTIONALIZED 3,4-DIHYDRO-2H-PYRANS BY HETERO - DIELS-ALDER REACTION OF AN ENAMINOKETONE WITH ENOL ETHERS, Monatshefte fuer Chemie, 126(12), 1995, pp. 1341-1348
Citations number
17
Categorie Soggetti
Chemistry
Journal title
Monatshefte fuer Chemie → ACNP
ISSN journal
00269247
Volume
126
Issue
12
Year of publication
1995
Pages
1341 - 1348
Database
ISI
SICI code
0026-9247(1995)126:12<1341:SOF3BH>2.0.ZU;2-3
Abstract
The hetero - Diels-Alder reaction of acetylbenzylamino)-2-cyano-1-phen yl-2-propen-1-one (3) with enol ethers (4) leads to diastereoisomeric cycloadducts 5 and 6 in good yields. The structure of the products is discussed in terms of configuration and preferred conformation. Reacti on of 5 with sulfuric acid yields 3-benzoyl-1,2-dihydropyridin-2-one ( 7).