Electrochemical oxidation of 4-monoalkyl-substituted 1,4-dihydropyridines

The electrochemical oxidation of 4-monoalkyl-substituted 1,4-dihydropyridines has been studied in an aprotic medium and in the presence of pyridine. In an aprotic medium the products of oxidation are both 4-alkyl-substituted and 4-unsubstituted pyridines or mixtures of them. On oxidation in acetonit...

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Bibliographic Details
Published in:Chemistry of heterocyclic compounds (New York, N.Y. 1965) N.Y. 1965), 2008-12, Vol.44 (12), p.1483-1490
Main Authors: Turovska, B, Goba, I, Turovskis, I, Grinberga, S, Belyakov, S, Stupnikova, S, Liepinsh, E, Stradins, J
Format: Article
Language:English
Subjects:
1,4-dihydropyridines
4-alkyl-substituted pyridines
alkyl radicals
Chemistry
Chemistry and Materials Science
electrochemical oxidation
exocyclic double bond
Organic Chemistry
Pharmacy
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Summary:The electrochemical oxidation of 4-monoalkyl-substituted 1,4-dihydropyridines has been studied in an aprotic medium and in the presence of pyridine. In an aprotic medium the products of oxidation are both 4-alkyl-substituted and 4-unsubstituted pyridines or mixtures of them. On oxidation in acetonitrile of 4-Et-, 4-n-Pr-, and 4-i-Bu-substituted dihydropyridines, 2-methylene-1,2,3,4-tetrahydropyridines were obtained in addition to the oxidized forms. In the presence of base the products of preparative electrolysis of the studied compounds were 4-alkyl-substituted pyridines. The exception was the 4-i-Pr- substituted dihydropyridine which was dealkylated on oxidation even in the presence of base.
ISSN:0009-3122
1573-8353
DOI:10.1007/s10593-009-0211-0