Acid-catalyzed deuterium exchange in Hantzsch-type dihydropyridines

Authors
Kocjan, D
Citation
D. Kocjan, Acid-catalyzed deuterium exchange in Hantzsch-type dihydropyridines, ACTA CHIM S, 45(3), 1998, pp. 355-361
Citations number
12
Categorie Soggetti
Chemistry
Journal title
ACTA CHIMICA SLOVENICA
ISSN journal
13180207 → ACNP
Volume
45
Issue
3
Year of publication
1998
Pages
355 - 361
Database
ISI
SICI code
1318-0207(1998)45:3<355:ADEIHD>2.0.ZU;2-3
Abstract
An interesting case of the acid-catalyzed deuterium exchange in methanol-d( 4) was found for 4-phenyl-1,4-dihydropyridine derivatives that belong to th e class of Ca-channel antagonists. Deuterium exchange of the C-alpha-methyl protons indicates formation of an enamine carbocation that can be describe d by three mesomeric models.