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Reaction of diketene with cyanothioacetamide: A convenient and regioselective method for the preparation of new 4(1H)-pyridone derivatives

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Chemistry of Heterocyclic Compounds Aims and scope

Abstract

The reaction of diketene with cyanothioacetamide in dry dioxane in the presence of triethylamine gives triethylammonium 3-cyano-6-methyl-4-oxo-1,4-dihydro-2-pyridinethiolate. The regioselective S-alkylation of this thiolate is a convenient method for the preparation of substituted 4(1H)-pyridones and also derivatives of thiazolo[3,2-a]pyridine and thieno[2,3-b]pyridine. The action of 2-amino-1,1,3-tricyanopropene on this thiolate leads to its transformation into a new heterocyclic system, namely, 5H-pyrido[2′,3′:4,5]thiopyrano[2,3-b]pyridine; treatment with iodine yields the oxidation product, namely, the corresponding bis(2-pyridyl) disulfide. The structure of isopropyl (3-cyano-6-methyl-4-oxo-1,4-dihydro-2-pyridinyl)thioacetate was confirmed by X-ray diffraction structural analysis.

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Authors and Affiliations

  1. “ChemEx” Laboratory, Vladimir Dal East-Ukrainian National University, 91034, Lugansk, Ukraine

    V. V. Dotsenko

  2. N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 117913, Moscow, Russia

    S. G. Krivokolysko

  3. Institute of Organic Chemistry, National Academy of Sciences of Ukraine, 02094, Kiev, Ukraine

    B. P. Litvinov

Authors
  1. V. V. Dotsenko
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  2. S. G. Krivokolysko
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  3. B. P. Litvinov
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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 5, pp. 716–725, May, 2007.

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Dotsenko, V.V., Krivokolysko, S.G. & Litvinov, B.P. Reaction of diketene with cyanothioacetamide: A convenient and regioselective method for the preparation of new 4(1H)-pyridone derivatives. Chem Heterocycl Compd 43, 599–607 (2007). https://doi.org/10.1007/s10593-007-0094-x

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