DIELS-ALDER REACTION OF THE N-PROTECTED 3-PHENYLTHIO-2(1H)DIHYDROPYRIDINONE DERIVATIVES

Authors
TORISAWA Y NAKAGAWA M TAKAMI H NAGATA T ALI MA HINO T
Citation
Y. Torisawa et al., DIELS-ALDER REACTION OF THE N-PROTECTED 3-PHENYLTHIO-2(1H)DIHYDROPYRIDINONE DERIVATIVES, Heterocycles, 39(1), 1994, pp. 277-292
Citations number
9
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Heterocycles → ACNP
ISSN journal
03855414
Volume
39
Issue
1
Year of publication
1994
Pages
277 - 292
Database
ISI
SICI code
0385-5414(1994)39:1<277:DROTN3>2.0.ZU;2-5
Abstract
Efficient methods for the preparation of N-protected 3-phenylthio-2(1H )dihydropyridinones from 2-piperidone and their Diels-Alder reaction w ith 2-trimetylsilyloxybutadiene are described. The role of the electro n-withdrawing N-protecting group in the dienophiles is rationalized in terms of the lowered energy level in LUMO.