Collect. Czech. Chem. Commun. 1989, 54, 1705-1715

On reactivity of 2,6-dichloro-3,5-diformyl-1,4,4-trimethyl-1,4-dihydropyridine

Antonín Kurfürst and Pavel Šebek

Department of Organic Chemistry, Prague Institute of Chemical Technology, 166 28 Prague 6


2,6-Dichloro-3,5-diformyl-4,4-dimethyl-1,4-dihydropyridines IIb-IId have been prepared by the Vilsmeier-Haack reaction of glutarimides I, and possible chemical transformations of the trimethyl derivative IIc have been examined. The bis-oxime IVa and bis-(2,4-dinitrophenylhydrazone) Vb are formed by the respective reactions of the formyl groups. The nucleophilic substitutions of chlorine give the corresponding derivatives IX-XII. The cyclocondensation reaction of compound IIc with the respective reagents gives the condensed heterocyclic derivatives VI, XIII, and XIV. The physico-chemical characteristics of the II-XIV compounds prepared are described.