Studies in [3,3] sigmatropic rearrangement: Regioselective cyclization of 5-(cyclohex-2-enyl)-6-hydroxy-1-methylquinolin-2(1H)-one

Authors
Majumdar, KC Biswas, P Ghosh, SK
Citation
Kc. Majumdar et al., Studies in [3,3] sigmatropic rearrangement: Regioselective cyclization of 5-(cyclohex-2-enyl)-6-hydroxy-1-methylquinolin-2(1H)-one, SYN COMMUN, 30(22), 2000, pp. 4113-4128
Citations number
38
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
SYNTHETIC COMMUNICATIONS
ISSN journal
00397911 → ACNP
Volume
30
Issue
22
Year of publication
2000
Pages
4113 - 4128
Database
ISI
SICI code
0039-7911(2000)30:22<4113:SI[SRR>2.0.ZU;2-K
Abstract
Thermal [3,3] sigmatropic rearrangement of 6-cydohex-2-enyloxy-1-methylquin olin-2(1H)-one (3) afforded 5-cyclohex-2-enyl-6-hydroxy-1-methylquinolin-2( 1H)-one (4) in 86% yield. Compound 4 on treatment with pyridine hydrotribro mide in CH2Cl2 gave exclusively non-bridged product 6 (85%) whereas compoun d 4 by a different route viz., acetylation followed by bromine addition and cyclization gave the bicyclic product 7 (80%). Compound 4 also furnished a bicyclic product 11 (80%) on treatment with cone. H2SO4.