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Fused sulfur-containing pyridine systems. 1. Synthesis and structures of tetrahydropyridothienopyridinone and tetrahydropyridothiopyranopyridinone derivatives

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Abstract

The reactions of N-methylmorpholinium 4-aryl(hetaryl)-5-cyano-2-oxo-1,2,3,4-tetrahydropyridine-6-thiolates with malononitrile and acetone in ethanol afforded substituted tetrahydropyridothienopyridinones. In the absence of acetone, tetrahydropyridothiopyranopyridinones were isolated as the major reaction products. The latter were also synthesized independently by the reactions of the above-mentioned thiolates with 2-amino-1,1,3-tricyanopropene. The structure of 2,4-diamino-10-(2-chlorophenyl)-3-cyano-5-imino-8-oxo-7,8,9,10-tetrahydro-5H-pyrido[2",3":2,3]thiopyrano[4,5-b]pyridine was established by X-ray diffraction analysis.

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Authors and Affiliations

  1. East Ukrainian National University, 20a-7 kv. Molodezhnyi, 91034, Lugansk, Ukraine

    V. V. Dotsenko & S. G. Krivokolysko

  2. Institute of Organic Chemistry, National Academy of Sciences of Ukraine, 5 ul. Murmanskaya, 02094, Kiev, Ukraine

    A. N. Chernega

  3. N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky prosp., 119991, Moscow, Russian Federation

    V. P. Litvinov

Authors
  1. V. V. Dotsenko
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  2. S. G. Krivokolysko
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  3. A. N. Chernega
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  4. V. P. Litvinov
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Dotsenko, V.V., Krivokolysko, S.G., Chernega, A.N. et al. Fused sulfur-containing pyridine systems. 1. Synthesis and structures of tetrahydropyridothienopyridinone and tetrahydropyridothiopyranopyridinone derivatives. Russian Chemical Bulletin 52, 969–977 (2003). https://doi.org/10.1023/A:1024420930528

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