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Synthesis and properties of 3-cyano-4-(4-cyanophenyl)-1,4-dihydropyridine-2(3H)-thiones

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Abstract

Piperidinium 3-cyano-4-(4-cyanophenyl)-1,4-dihydropyridine-2(3H)-thiolates were obtained by the condensation of 1,3-dicarbonyl compounds, 4-cyanobenzaldehyde, and cyanothioacetamide in the presence of an equimolar amount of piperidine. The acidification of these thiolates gave the corresponding 1,4-dihydropyridine-2(3H)-thiones and pyridine-2(1H)-thione. Alkylation of 1,4-dihydropyridine-2-thiolates or the reaction mixture of the three-carbon condensation using iodacetamide gave 2-carbamoylmethylthio-1,4,5,6-tetrahydro- or 1,4-dihydropyridines, which were characterized by their conversion to 4,7-dihydrothieno[2,3-b]pyridines.

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Authors
  1. A. Krauze
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  2. G. Duburs
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Additional information

Latvian Institute of Organic Synthesis, LV-1006, Riga, Latvia

Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 6, pp. 794–798, June, 2000.

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Krauze, A., Duburs, G. Synthesis and properties of 3-cyano-4-(4-cyanophenyl)-1,4-dihydropyridine-2(3H)-thiones. Chem Heterocycl Compd 36, 693–697 (2000). https://doi.org/10.1007/BF02297678

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  • DOI: https://doi.org/10.1007/BF02297678

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