Synthesis and reactions of some 2-vinyl-3H-quinazolin-4-ones

Citation
A. Witt et J. Bergman, Synthesis and reactions of some 2-vinyl-3H-quinazolin-4-ones, TETRAHEDRON, 56(37), 2000, pp. 7245-7253
Citations number
38
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON
ISSN journal
00404020 → ACNP
Volume
56
Issue
37
Year of publication
2000
Pages
7245 - 7253
Database
ISI
SICI code
0040-4020(20000908)56:37<7245:SAROS2>2.0.ZU;2-8
Abstract
A simple, high-yielding synthesis of 2-vinyl-3H-quinazolin-4-one, 2-(1-chlo rovinyl)-3H-quinazolin-4-one and 2-(1-bromovinyl)-3H-quinazolin-4-one. The 2-vinylquinazolinones 11a and 14 participate readily in nucleophilic additi on reactions. Treatment with both carbon and nitrogen nucleophiles results in a clean conversion into a variety of 2-substituted 3H-quinazolin-4-one d erivatives. The 2-(1-halovinyl)-3H-quinazolin-4-ones 11b and Ile reacted wi th carbon nucleophiles to give several derivatives of 2-substituted 3H-quin azolin-4-one, such as dihydrofurancarboxylic ethyl ester 23. (C) 2000 Elsev ier Science Ltd. All rights reserved.