INTRAMOLECULAR REISSERT-HENZE REACTION OF ISOXAZOLO[2,3-A]PYRIDINIUM SALT - FACILE SYNTHESIS OF FUNCTIONALIZED PHENACYLPYRIDINES FROM ETHYNYLPYRIDINES

Authors
NISHIWAKI N ARIGA M KOMATSU M OHSHIRO Y
Citation
N. Nishiwaki et al., INTRAMOLECULAR REISSERT-HENZE REACTION OF ISOXAZOLO[2,3-A]PYRIDINIUM SALT - FACILE SYNTHESIS OF FUNCTIONALIZED PHENACYLPYRIDINES FROM ETHYNYLPYRIDINES, Heterocycles, 43(6), 1996, pp. 1179-1184
Citations number
15
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Heterocycles → ACNP
ISSN journal
03855414
Volume
43
Issue
6
Year of publication
1996
Pages
1179 - 1184
Database
ISI
SICI code
0385-5414(1996)43:6<1179:IRROIS>2.0.ZU;2-Z
Abstract
Oxidation of 2-(phenylethynyl)pyridine with H2O2-AcOH gave isoxazolo[2 ,3-a]pyridinium acetate, which was successively attacked by alcohols i n the presence of Na2CO3 to afford 6-alkoxy-substituted 2-phenacylpyri dines in moderate yields. It was also possible to introduce amino or a lkylthio functionality onto the pyridine ring by similar process. The present reaction is a new example of intramolecular Reissert-Henze-typ e reaction.