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Synthesis and properties of 6-methyl-4-(m-nitrophenyl)-3-cyanopyridin-2(1H)-ones, the corresponding pyridine-2(1H)-thiones, and their hydrogenated analogs

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Chemistry of Heterocyclic Compounds Aims and scope

Abstract

The condensation of 4-pyridylacetone, m-nitrobenzaldehyde, and cyanoacetamide (cyanothioacetamide) in the presence of bases was used to obtain 5-pyridyl-substituted 6-methyl-4-(m-nitrophenyl)-3-cyanopyridin-2(1H)-ones, the corresponding pyridine-2(1H)-thiones, and their hydrogenated analogs. 2-Carbamoylmethylthiopyridine was isolated in the alkylation of 5-(4′-pyridyl)pyridine-2(1H)-thione with iodoacetamide under mild conditions, while 2-carbamoylthio-5-(N-carbamoylmethyl-4′-pyridyl)pyridine iodide was isolated under more severe conditions.

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Authors and Affiliations

  1. Institute of Organic Synthesis, Latvian Academy of Sciences, 226006, Riga

    A. A. Krauze, H. -I. Ensch & G. Ya. Dubur

  2. Arzneimittelwerk Dresden GmbH, Radebeul

    A. A. Krauze, H. -I. Ensch & G. Ya. Dubur

Authors
  1. A. A. Krauze
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  2. H. -I. Ensch
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  3. G. Ya. Dubur
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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 12, pp. 1674–1679, December, 1991.

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Krauze, A.A., Ensch, H.I. & Dubur, G.Y. Synthesis and properties of 6-methyl-4-(m-nitrophenyl)-3-cyanopyridin-2(1H)-ones, the corresponding pyridine-2(1H)-thiones, and their hydrogenated analogs. Chem Heterocycl Compd 27, 1347–1352 (1991). https://doi.org/10.1007/BF00515580

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  • DOI: https://doi.org/10.1007/BF00515580

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