SYNTHESIS, CARDIOVASCULAR ACTIVITY, AND ELECTROCHEMICAL OXIDATION OF NITRILES OF 5-ETHOXYCARBONYL-2-METHYLTHIO-1,4-DIHYDROPYRIDINE-3-CARBOXYLIC ACID

Abstract

Nitriles of 4-aryl-5-ethoxycarbonyl-2-methylthio-1,4-dihydropyridine-3-carboxylic acid have been obtained by the methylation of 1,4-dihydropyridine-2-thiolates; of 1,4-dihydropyridine-2(3H)-thiones in the presence of a stoichiometric amount of piperidine, and of a mixture of 1,4,5,6-tetrahydro- and 1,4-dihydropyridine-2-thiolates with methyl iodide. One-pot multicomponent synthesis has also been used in the condensation of ethyl 2-arylmethyleneacetoacetate, 2-cyanothioacetamide, piperidine, and methyl iodide; of ethyl acetoacetate, 3-aryl-2-cyanothioacrylamide, piperidine, and methyl iodide; and of ethyl acetoacetate, an aromatic aldehyde, 2-cyanothioacetamide, piperidine, and methyl iodide. The latter, a five-component method, takes place rapidly and under mild conditions, it is efficient (yields of 75-96%, economy of time, labour, and resources) and "green" (there is no need to synthesize lachrymators, such as 3-aryl-2-cyanothioacrylamides).The cardiovascular activity and the electrochemical oxidation of the synthesized 2-methylthio-1,4-dihydropyridines have been investigated. A comparative analysis has been carried out of the ability towards electrochemical oxidation as a function of the electronic properties of the substituent at position 4 of the heterocycle.

How to Cite
Krauze, A.; Baumane, L.; Sile, L.; Chernova, L.; Vilums, M.; Vitolina, R.; Duburs, G.; Stradins, J. Chem. Heterocycl. Compd. 2004, 40, 876. [Khim. Geterotsikl. Soedin. 2004, 1022.]

For this article in the English edition, see DOI 10.1023/B:COHC.0000044570.13567.74