Reaction of diketene with cyanothioacetamide: A convenient and regioselective method for the preparation of new 4(1H)-pyridone derivatives |
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Authors: | V. V. Dotsenko S. G. Krivokolysko B. P. Litvinov |
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Affiliation: | (1) “ChemEx” Laboratory, Vladimir Dal East-Ukrainian National University, 91034 Lugansk, Ukraine;(2) N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 117913 Moscow, Russia;(3) Institute of Organic Chemistry, National Academy of Sciences of Ukraine, 02094 Kiev, Ukraine |
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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. __________ Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 5, pp. 716–725, May, 2007. |
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Keywords: | diketene, 4(1H)-pyridones 5H-pyrido[2′ ,3′ :4,5]thiopyrano[2,3-b]pyridines thiazolo-[3,2-a]pyridines thieno[2,3-b]pyridines cyanothioacetamide S-alkylation X-ray diffraction structural analysis Thorpe-Ziegler cyclization cyclocondensation |
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