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Chemistry of Heterocyclic Compounds

, Volume 40, Issue 7, pp 876–887 | Cite as

Synthesis, Cardiovascular Activity, and Electrochemical Oxidation of Nitriles of 5-Ethoxycarbonyl-2-methylthio-1,4-dihydropyridine-3-carboxylic Acid

  • A. Krauze
  • L. Baumane
  • L. Sile
  • L. Chernova
  • M. Vilums
  • R. Vitolina
  • G. Duburs
  • J. Stradins
Article

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.

1,4-dihydropyridines cardiovascular activity one-pot multicomponent synthesis electrochemical oxidation 

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Copyright information

© Plenum Publishing Corporation 2004

Authors and Affiliations

  • A. Krauze
  • L. Baumane
  • L. Sile
  • L. Chernova
  • M. Vilums
  • R. Vitolina
  • G. Duburs
  • J. Stradins

There are no affiliations available

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