REACTION OF BETA-NITROENONES WITH THIOPHENOL - SYNTHESIS OF 5-HYDROXY-4-(PHENYLTHIO)-2-ISOXAZOLINE 2-OXIDES

Authors
SCHNEIDER R GERARDIN P LOUBINOUX B RIHS G
Citation
R. Schneider et al., REACTION OF BETA-NITROENONES WITH THIOPHENOL - SYNTHESIS OF 5-HYDROXY-4-(PHENYLTHIO)-2-ISOXAZOLINE 2-OXIDES, Tetrahedron, 51(17), 1995, pp. 4997-5010
Citations number
32
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron → ACNP
ISSN journal
00404020
Volume
51
Issue
17
Year of publication
1995
Pages
4997 - 5010
Database
ISI
SICI code
0040-4020(1995)51:17<4997:ROBWT->2.0.ZU;2-Y
Abstract
A new synthesis of 2-isoxazoline 2-oxides starting from unsaturated ni tro compounds is described. A facile and convenient preparation of bet a-alkyl substituted beta-nitroenones and their conversion to beta-nitr osulfides are recorded. Treatment of these compounds with potassium te a-butoxide at -78 degrees C followed by immediate quenching with aceti c acid provides access to 5-hydroxy-4-(phenylthio)-2-isoxazoline 2-oxi des via intramolecular addition of the nitronate anion to the carbonyl group.