Abstract
Cyclopentylidene- and cyclohexylidene(cyano)acetamides reacted with malononitrile and cyano-(thioacetamide) according to the Michael pattern with exchange of the methylene components to give substituted 1-amino-2,6,6-tricyano-1,3-cyclohexadienes and thieno[2,3-d]pyrimidine-4(3H)-thiones. Condensation of cyclopentylidene- and cyclohexylidene(cyano)acetamide with 1,3-dicarbonyl compounds afforded 4,6-di-methyl-3-cyanopyridine-2(1H)-thione and morpholinium 4-methyl-6-oxo-3-cyano-1,6-dihydropyridine-2-thiolate which were converted into substituted 2-alkylsulfanylpyridines, thieno[2,3-b]pyridines, thiazolo[3,2-a]pyridine, and 2H-[1,3]thiazino[3,2-a]pyridine.
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REFERENCES
Bergman, E.D., Ginsburg, D., and Pappo, R., Organic Reactions, Adams, R., Ed., New York: Wiley, 1959, vol. 10. Translated under the title Organicheskie reaktsii, Moscow: Inostrannaya Literatura, 1963, vol. 10, p. 181; The Chemistry of Alkenes, Patai, S., Ed., London: Intersci., 1964. Translated under the title Khimiya alkenov, Leningrad: Khimiya, 1969, p. 260; Gorobets, E.V., Miftakhov, M.S., and Valeev, F.A., Usp. Khim., 2000, vol. 69, p. 1091.
Litvinov, V.P., Rodinovskaya, L.A., Sharanin, Yu.A., Shestopalov, A.M., and Senning, A., Sulfur Rep., 1992, vol. 13, p. 1; Dyachenko, V.D., Doctoral (Chem.) Dissertation, Moscow, 1998.
Litvinov, V.P., Krivokolysko, S.G., and Dyachenko, V.D., Khim. Geterotsikl. Soedin., 1999, p. 579.
Borisov, V.N., Sovremennye problemy organicheskoi khimii (Current Problems in Organic Chemistry), Ogloblin, K.A., Ed., Leningrad: Leningr. Gos. Univ., 1975, p. 89.
Sharanin, Yu.A. and Shestopalov, A.M., Zh. Org. Khim., 1989, vol. 25, p. 1331; Dyachenko, V.D. and Litvinov, V.P., Khim. Geterotsikl. Soedin., 1998, p. 213; Krivokolysko, S.G. and Dyachenko, V.D., Ukr. Khim. Zh., 1996, vol. 62, p. 61; Dyachenko, V.D., Krivokolysko, S.G., and Litvinov, V.P., Mendeleev Commun., 1998, p. 23.
Mirek, V., Adamczyc, M., and Mokrosz, M., Synthesis, 1980, p. 296.
Gewald, K. and Schindler, R., J. Prakt. Chem., 1990, vol. 332, p. 223.
Dyachenko, V.D., Sharanin, Yu.A., Shestopalov, A.M., Rodinovskaya, L.A., Turov, A.V., Litvinov, V.P., and Promonenkov, V.K., Zh. Obshch. Khim., 1990, vol. 60, p. 2384.
Schmidt, U. and Kubitzek, H., Chem. Ber., 1960, vol. 93, p. 1559.
Alder, R.W., Goode, N.C., King, T.J., Mellor, J.M., and Miller, B.W., J. Chem. Soc., Chem. Comm., 1976, p. 173; Burke-Laing, M. and Laing, M., Acta Crystallogr., Sect. B, 1976, vol. 32, p. 32164.
Kuleshova, L.N. and Zorkii, P.M., Acta Crystallogr., Sect. B, 1981, vol. 37, p. 1363.
Freimanis, Ya.F., Khimiya enaminoketonov, enaminoiminov, enaminotionov (Chemistry of Enaminoketones, Enaminoimines, and Enaminothiones), Riga: Zinatne, 1974.
Sheldric, G.M. SHELXS-86. Program for the Solution of Crystal Structures, Göttingen: Univ. of Göttingen, 1986; Sheldric, G.M., SHELXL-93. Program for the Refinement of Crystal Structures, Göttingen: Univ. of Göttingen, 1993.
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Dyachenko, V.D., Dyachenko, A.D. & Chernega, A.N. Synthesis of Substituted 1,3-Cyclohexadienes, Pyridine-2(1H)-thiones, and Thieno[2,3-d]pyrimidine- 4(3H)-thiones by the Michael Reaction. Russian Journal of Organic Chemistry 40, 397–406 (2004). https://doi.org/10.1023/B:RUJO.0000034978.81993.bd
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DOI: https://doi.org/10.1023/B:RUJO.0000034978.81993.bd