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4-(3-Cyanopyridin-2-ylthio)acetoacetates in synthesis of heterocycles
Authors:Rodinovskaya  L A  Shestopalov  A M  Gromova  A V
Institution:(1) N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky prosp., 119991 Moscow, Russian Federation
Abstract:Substituted 2-amino-4-aryl-3-cyano-5-oxo-5,6-dihydro-4H-pyrano2,3-d]pyrido3",2":4,5]thieno3,2-b]pyridines were synthesized by the reactions of 4-hydroxy-1H-thieno2,3-b;4,5-b]dipyridin-2-ones with arylidenemalononitriles or by the three-component reactions of hydroxythienodipyridinones with aldehydes and malononitrile in DMF in the presence of triethylamine. Methods for syntheses of substituted 3-alkoxycarbonyl-6-amino-4-aryl-2-(3-cyanopyridin-2-ylthiomethyl)-4H-pyrans were developed on the basis of the reactions of 4-(3-cyanopyridin-2-ylthio)acetoacetates and arylidenemalononitriles or aldehydes and malononitrile. Ethyl 4-(3-cyanopyridin-2-ylthio)acetoacetate and 4-methoxybenzylidenecyanothioacetamide were used for the synthesis of 6-(pyridin-2-ylthiomethyl)-3-cyanopyridine-2(1H)-thione.
Keywords:malononitrile  arylidenemalononitriles  3-cyanopyridine-2(1H)-thiones  substituted 5  6-dihydro-5-oxo-4H-pyrano[2  3-d]pyrido[3"  2":4  5]thieno[3  2-b]pyridines  4-hydroxy-1H-thieno[2  3-b  4  5-b]dipyridin-2-ones  4-(3-cyanopyridin-2-ylthio)acetoacetates  3-alkoxycarbonyl-6-amino-4-aryl-2-(3-cyanopyridin-2-ylthiomethyl)-4H-pyrans  3-cyanopyridine-6-(pyridin-2-ylthiomethyl)-2(1H)-thione
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