A NEW STRAIGHTFORWARD FORMATION OF AMINOISOXAZOLES FROM ISOCYANIDES

Citation
C. Buron et al., A NEW STRAIGHTFORWARD FORMATION OF AMINOISOXAZOLES FROM ISOCYANIDES, Tetrahedron letters, 38(46), 1997, pp. 8027-8030
Citations number
17
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
ISSN journal
00404039
Volume
38
Issue
46
Year of publication
1997
Pages
8027 - 8030
Database
ISI
SICI code
0040-4039(1997)38:46<8027:ANSFOA>2.0.ZU;2-M
Abstract
The reaction of alpha-bromoketone oximes with isocyanides and sodium c arbonate leads to a new formation of 5-aminoisoxazole derivatives. The reaction probably involves the intermediacy of a nitrosoalkene genera ted in situ. Good yields are obtained for electron deficient ketone ox imes such as ethyl bromopyruvate oxime; the use of a trifluoromethyl s ubstituted oxime gives a high efficient formation of trifluoromethyl i soxazoles. (C) 1997 Published by Elsevier Science Ltd.