Formation and destruction of diazine ring under conditions of the Vilsmeier-Haack formylation of 4-dialkylaminonaphthalic acid derivatives

Authors
Patsenker, LD Yermolenko, IG Artyukhova, YY Baumer, VN Krasovitskii, BM
Citation
Ld. Patsenker et al., Formation and destruction of diazine ring under conditions of the Vilsmeier-Haack formylation of 4-dialkylaminonaphthalic acid derivatives, TETRAHEDRON, 56(37), 2000, pp. 7319-7323
Citations number
8
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON
ISSN journal
00404020 → ACNP
Volume
56
Issue
37
Year of publication
2000
Pages
7319 - 7323
Database
ISI
SICI code
0040-4020(20000908)56:37<7319:FADODR>2.0.ZU;2-G
Abstract
The quaternized 1,3-diazine ring formation qualified as a particular case o f the t-amino effect has been found under conditions of the Vilsmeier-Haack formylation of 4-dialkylaminonaphthalic acid derivatives. The diazinium ri ng is hydrolyzed in alkaline media with dealkylation, and 3-dimethylamino-4 -alkylamino derivatives are formed. (C) 2000 Elsevier Science Ltd. All righ ts reserved.