Studies in aza-Claisen rearrangement: synthesis of dimedone-annelated unusual heterocycles

Authors
Majumdar, KC Samanta, SK
Citation
Kc. Majumdar et Sk. Samanta, Studies in aza-Claisen rearrangement: synthesis of dimedone-annelated unusual heterocycles, TETRAHEDRON, 57(23), 2001, pp. 4955-4958
Citations number
25
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON
ISSN journal
00404020 → ACNP
Volume
57
Issue
23
Year of publication
2001
Pages
4955 - 4958
Database
ISI
SICI code
0040-4020(20010604)57:23<4955:SIARSO>2.0.ZU;2-T
Abstract
A number of 3-N-(4'-aryloxybut-2'-ynyl)N-methyl amino-5,5-dimethyl cyclohex -2-enones are synthesized in 62-65% yield by refluxing 3-chloro-5,5-dimethy l cyclohex-2-enone with a number of 4-aryloxy-4-chlorobut-2-ynes in ethanol for 4 h. The amines are then heated in refluxing chlorobenzene to give 7,7 -dimethyl-1,2,3,6,7,8-hexahydro-4-aryloxymethylene-1-methyl quinoiine-5-one in 75-80% yields. (C) 2001 Elsevier Science Ltd. All rights reserved.