METALATION OF 3-PHENYL-2-ISOXAZOLIN-5-ONE - REACTION WITH SOME ELECTROPHILES

Authors
BAHAMONDES C TEJOS M MOLINARI A OLIVA A
Citation
C. Bahamondes et al., METALATION OF 3-PHENYL-2-ISOXAZOLIN-5-ONE - REACTION WITH SOME ELECTROPHILES, Boletin de la Sociedad Chilena de Quimica, 39(4), 1994, pp. 273-278
Citations number
17
Categorie Soggetti
Chemistry
Journal title
Boletin de la Sociedad Chilena de Quimica → ACNP
ISSN journal
03661644
Volume
39
Issue
4
Year of publication
1994
Pages
273 - 278
Database
ISI
SICI code
0366-1644(1994)39:4<273:MO3-RW>2.0.ZU;2-Q
Abstract
The deprotonation of 3-phenyl-2-isoxazolin-5-one 1 with n-butyllithium or lithium diisopropylamide (LDA) at 0 degrees C, followed by the rea ction with alkyl iodides or ethyl chloroformiate results in the format ion of N-substituted-3-phenyl-3-isoxazolin-5-one. With acyl chlorides, N-substituted, 4-substituted and 5-0-substituted derivatives of 1 are formed, and similar results are observed with phenyl and butyl chloro formiates.