The Vilsmeier cyclization of 2'-azido and 2'-aminochalcones - a mild one pot synthesis of 2-aryl-4-chloroquinoline and its N-formyl-1,2-dihydro derivatives

Authors
Akila, S Selvi, S Balasubramanian, K
Citation
S. Akila et al., The Vilsmeier cyclization of 2'-azido and 2'-aminochalcones - a mild one pot synthesis of 2-aryl-4-chloroquinoline and its N-formyl-1,2-dihydro derivatives, TETRAHEDRON, 57(16), 2001, pp. 3465-3469
Citations number
33
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON
ISSN journal
00404020 → ACNP
Volume
57
Issue
16
Year of publication
2001
Pages
3465 - 3469
Database
ISI
SICI code
0040-4020(20010416)57:16<3465:TVCO2A>2.0.ZU;2-N
Abstract
The Vilsmeier cyclization of 2'-aminochalcones provides a mild one pot synt hesis of 2-aryl-4-chloro-N-formyl-1,2-dihydroquinolines. The scope of the r eaction has been extended for the synthesis of quinolines themselves, by re placing 2'-aminochalcones with 2'-azidochalcones as the starting material. The yields are reasonably good and a plausible mechanism for the formation of the products in each case has been discussed. (C) 2001 Elsevier Science Ltd. All rights reserved.