SYNTHESIS OF AZINYLVINYLPYRIDAZINES - A GENERAL NOTE ON THE ISOMERIZATION OF HETARYLDIENAMINES

Authors
KOTSCHY A HAJOS G TIMARI G MESSMER A
Citation
A. Kotschy et al., SYNTHESIS OF AZINYLVINYLPYRIDAZINES - A GENERAL NOTE ON THE ISOMERIZATION OF HETARYLDIENAMINES, Journal of organic chemistry, 61(13), 1996, pp. 4423-4426
Citations number
16
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Journal of organic chemistry → ACNP
ISSN journal
00223263
Volume
61
Issue
13
Year of publication
1996
Pages
4423 - 4426
Database
ISI
SICI code
0022-3263(1996)61:13<4423:SOA-AG>2.0.ZU;2-8
Abstract
Azinyldienamines underwent Diels Alder reaction of inverse electron de mand with 1,2,4,5-tetrazine diester to give azinylvinylpyridazines. Co mparison of the products obtained from mono-, di-, and triazinyldienam ines revealed that, in some cases, isomerization of the olefinic side chain occurred which can be rationalized by the tautomeric conditions of the intermediates bearing these azine moieties. These experimental findings supported also by semiempirical calculations suggest the impo rtance of the influence of the hetaryl group in such isomerizations.