Synthesis of 3a, 4-dihydro-8-substituted-3H-isoxazolo [c-4,3] thiapyrano [5,6-3,2] quinolines

Authors
Prabhuswamy, B Ambekar, SY
Citation
B. Prabhuswamy et Sy. Ambekar, Synthesis of 3a, 4-dihydro-8-substituted-3H-isoxazolo [c-4,3] thiapyrano [5,6-3,2] quinolines, SYN COMMUN, 29(20), 1999, pp. 3477-3485
Citations number
16
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
SYNTHETIC COMMUNICATIONS
ISSN journal
00397911 → ACNP
Volume
29
Issue
20
Year of publication
1999
Pages
3477 - 3485
Database
ISI
SICI code
0039-7911(1999)29:20<3477:SO34[T>2.0.ZU;2-8
Abstract
Condensation of 2-chloro-3-formylquinoline 1a-c with allylthiol 2 afforded 2-allysulfanyl-3-formylquinolines 3a-c, Oximation followed by oxidation of 3a-c with NaOCl or chloramine-T, in cold or mercuric acetate resulted in th e formation of respective nitrile oxides, which underwent insitu intramolec ular 1,3-dipolar cycloaddition reaction and afforded the title compounds 5a -c in high yield.