IRON DICHLORIDE INDUCED ISOMERIZATION OR REDUCTIVE CLEAVAGE OF ISOXAZOLES - A FACILE SYNTHESIS OF 2-CARBOXY-AZIRINES

Authors
AURICCHIO S BINI A PASTORMERLO E TRUSCELLO AM
Citation
S. Auricchio et al., IRON DICHLORIDE INDUCED ISOMERIZATION OR REDUCTIVE CLEAVAGE OF ISOXAZOLES - A FACILE SYNTHESIS OF 2-CARBOXY-AZIRINES, Tetrahedron, 53(31), 1997, pp. 10911-10920
Citations number
29
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron → ACNP
ISSN journal
00404020
Volume
53
Issue
31
Year of publication
1997
Pages
10911 - 10920
Database
ISI
SICI code
0040-4020(1997)53:31<10911:IDIIOR>2.0.ZU;2-P
Abstract
5-Alkoxy-isoxazoles and N,N-disubstituted-5-isoxazolamines were found to isomerize to azirine derivatives by the use of iron dichloride as c atalyst. On the contrary 5-alkyl- and 5-aryl-isoxazoles in the presenc e of the same salt, undergo reductive cleavage to enaminoketones. A co mmon reaction intermediate is proposed. (C) 1997 Elsevier Science Ltd.