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Oxidation of thioamides with the DMSO–HCl system: a convenient and efficient method for the synthesis of 1,2,4-thiadiazoles, isothiazolo-[5,4-b]pyridines, and heterocyclic disulfides

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Chemistry of Heterocyclic Compounds Aims and scope

Brief heating of 3-aryl-2-cyanothioacrylamides in the DMSO–HCl system gave (2E,2′E)-2,2′-(1,2,4-thia-diazol-3,5-diyl)bis(3-arylacrylonitriles). Under the same conditions, cyclic thioamides (derivatives of 2-thioxo-1,2-dihydropyridine-3-carbonitrile and quinoxaline-2(1H)-thione) gave good yields of the bis(hetaryl) disulfides. Ethyl 4-(4-chlorophenyl)-5-cyano-2-phenyl-6-thioxo-1,4,5,6-tetra-hydropyridine-3-carboxylate gave a mixture of oxidation products at the sulfur atom and the hetero-cycle when treated with the DMSO–HCl system. Oxidation of N-aryl-4,6-dimethyl-2-thioxo-1,2-di-hydropyridine-3-carboxamides gave isothiazolo[5,4-b]pyridines.

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Authors and Affiliations

  1. “ChemEx” Laboratory, Vladimir Dal’ Eastern Ukrainian National University, 20-A Molodezhny Kv., Lugansk, 91034, Ukraine

    V. V. Dotsenko & S. G. Krivokolysko

Authors
  1. V. V. Dotsenko
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  2. S. G. Krivokolysko
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Correspondence to V. V. Dotsenko.

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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 4, pp. 682-690, April, 2013.

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Dotsenko, V.V., Krivokolysko, S.G. Oxidation of thioamides with the DMSO–HCl system: a convenient and efficient method for the synthesis of 1,2,4-thiadiazoles, isothiazolo-[5,4-b]pyridines, and heterocyclic disulfides. Chem Heterocycl Comp 49, 636–644 (2013). https://doi.org/10.1007/s10593-013-1291-4

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