A versatile and efficient method for the synthesis of benz[a]azulenic enones starting from readily available o-(2-furyl)cycloheptatrienylbenzenes

Authors
Sasabe, M Houda, Y Takagi, H Sugane, T Bo, X Yamamura, K
Citation
M. Sasabe et al., A versatile and efficient method for the synthesis of benz[a]azulenic enones starting from readily available o-(2-furyl)cycloheptatrienylbenzenes, J CHEM S P1, (22), 2000, pp. 3786-3790
Citations number
41
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1
ISSN journal
14704358 → ACNP
Issue
22
Year of publication
2000
Pages
3786 - 3790
Database
ISI
SICI code
1470-4358(2000):22<3786:AVAEMF>2.0.ZU;2-N
Abstract
A facile, one-pot synthesis of beta-(benz[a]azulen-10-yl)-alpha,beta -unsat urated ketones from the corresponding o-(2-furyl)cycloheptatrienylbenzenes is reported. A mechanism involving a novel ring-opening cyclisation reactio n by the intramolecular attack of the tropylium ion to the 2-position of th e furan ring is proposed.