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New synthetic approach to substituted 2-alkylsulfanyl-4,6-diaryl(heteryl)-1,4-dihydropyridine-, pyridine-, and thieno[2,3-b]pyridine-3-carbonitriles

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Abstract

Reactions of 1,3-diaryl(heteryl)prop-2-ene-1-thiones with 2-cyanoethanethio(seleno)-amides and alkyl halides led to the formation of substituted 2-alkylsulfanyl-4,6-diaryl(heteryl)-1,4-dihydropyridine-, pyridine-, and thieno[2,3-b]pyridine-3-carbonitriles.

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References

  1. Tasaka, S., Kine, A., Omori, H., Tanabe, Y., and Gomi, N., EP Patent Appl. no. 1055672, 2000; Chem. Abstr., 2001, no. 19O117P.

  2. Burke, P.J. and Kuox, R.J., GB Patent Appl. no. 2365338, 2002; Ref. Zh. Khim., 2002, no. 19O62P.

  3. Tirzite, D., Krauze, A., Zubareva, A., Tirzitis, G., and Duburs, G., Chem. Heterocycl. Compd., 2002, vol. 38, p. 795.

    Article  CAS  Google Scholar 

  4. Sirisha, K., Bikshapathi, D., Achaiah, G., and Reddy, V.M., Eur. J. Med. Chem., 2011, vol. 46, p. 1564.

    Article  CAS  Google Scholar 

  5. Gein, V.L., Kazantseva, M.I., Kurbatova, A.A., and Voronina, E.V., Pharm. Chem. J., 2011, vol. 45, p. 474.

    Article  CAS  Google Scholar 

  6. Nakajo, A., Tokumasu, M., Kito, M., Takahara, A., Ono, Y., Takeda, T., Kajiagava, Y., and Kaganei, H., US Patent no. 6610717, 2003; Ref. Zh. Khim., 2004, no. 19O83P.

  7. Jacobson, K.A. and Li, A.-H., US Patent no. 6376521, 2002; Ref. Zh. Khim., 2003, no. 19O87P.

  8. Krauze, A., Baumane, L., Sile, L., Chernova, L., Vilums, M., Vitolina, R., Duburs, G., and Stradins, J., Chem. Heterocycl. Compd., 2004, vol. 40, p. 876.

    Article  CAS  Google Scholar 

  9. Barfacker, L., Kolkhof, P., Schlemmer, K.-H., Grosser, R., and Nitsche, A., German Patent Appl. no. 102006044696, 2008; Ref. Zh. Khim., 2009, no. 19O121P.

  10. Osolodkin, D.I., Kozlovskaya, L.I., Dueva, E.V., Dotsenko, V.V., Rogova, Y.V., Frolov, K.A., Krivokolysko, S.G., Romanova, E.G., Morozov, A.S., Karganova, G.G., Palyulin, V.A., Pentovski, V.M., and Zefirov, N.S., Med. Chem. Lett., 2013, vol. 4, p. 869.

    Article  CAS  Google Scholar 

  11. Nakujo, A., Tokumasu, M., Kito, M., Takahara, A., Ono, Y., Takeda, T., Kajigaya, Y., and Koganei, H., EP Patent Appl., no. 1191022, 2002; Ref. Zh. Khim., 2002, no. 19O69P.

  12. Niwa, S., Ohno, S., Takahara, A., and Kito, M., EP Patent Appl., no. 1123923, 2001; Ref. Zh. Khim., 2002, no. 19O112P.

  13. Ertan, R., Ayhan-Kilcigil, G., and Tunobilek, M., Turk. Bull. Hyg. Experim. Biol., 1998, vol. 55, p. 55; Ref. Zh. Khim., 2000, no. 06-19Zh218.

    CAS  Google Scholar 

  14. Litvinov, V.P., Krivokolysko, S.G., and Dyachenko, V.D., Chem. Heterocycl. Compd., 1999, vol. 35, p. 509.

    Article  CAS  Google Scholar 

  15. Livinov, V.P., Russ. Chem. Rev., 2006, vol. 75, p. 577.

    Article  Google Scholar 

  16. Eisnen, U. and Kuthan, I., Chem. Rev., 1972, vol. 72, p. 1.

    Article  Google Scholar 

  17. Litvinov, V.P., Sharanin, Yu.A., Shestopalov, A.M., and Dyachenko, V.D., Syntett, 1992, p. 87.

    Google Scholar 

  18. Attia, A.M. and Elgemeie, G.H., Synth. Commun., 2003, vol. 33, p. 2243.

    Article  CAS  Google Scholar 

  19. Leistner, S., Ludwig, A., Reichelf, C., and Schulze, A., EP Patent Appl. no. 1681292, 2006; Ref. Zh. Khim., 2007, no. 19O116P.

  20. Cywin, C.L., Chen, Z., Fleck, R.W., Hao, M.-H., Hickey, E., Liu, W., Marshall, D.R., Nemoto, P., Sorcek, R.J., Sun, S., Wu, J.-P., Morwick, T., and Emeigh, J., US Patent no. 6964956, 2005; Ref. Zh. Khim., 2006, no. 19O69P.

  21. Reichelf, C., Ludwig, A., and Leistner, S., EP Patent Appl. no. 1683799, 2006; Ref. Zh. Khim., 2007, no. 19O115P.

  22. Vatsuro, K.V. and Mishchenko, G.L., Imennye reaktsii v organicheskoi khimii, Moscow: Khimiya, 1976.

    Google Scholar 

  23. Itogi nauki i tekhniki. Organicheskaya khimiya, Moscow: VINITI, 1990, vol. 16.

  24. Sharanin, Yu.A., Dyachenko, V.D., Litvinov, V.P., and Turov, A.V., Zh. Obshch. Khim., 1991, vol. 61, p. 942.

    CAS  Google Scholar 

  25. Litvinov, V.P., Rodinovskaya, L.A., Sharanin, Yu.A., Shestopalov, A.M., and Senning, A., Sulfur Rep., 1992, vol. 13, p. 1.

    Article  CAS  Google Scholar 

  26. Sharanin, Yu.A., Krivokolysko, S.G., and Dyachenko, V.D., Zh. Org. Khim., 1994, vol. 30, p. 581.

    CAS  Google Scholar 

  27. Dyachenko, V.D., Russ. J. Gen. Chem., 2005, vol. 75, p. 440.

    Article  CAS  Google Scholar 

  28. Dyachenko, V.D., Russ. J. Gen. Chem., 2005, vol. 75, p. 447.

    Article  CAS  Google Scholar 

  29. Pretsch, E., Buhlmann, P., and Affolter, C., Structure Determination of Organic Compounds, Tables of Spectra Data, Berlin: Springer, 2000.

    Book  Google Scholar 

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Correspondence to I. V. Dyachenko.

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Original Russian Text © I.V. Dyachenko, V.D. Dyachenko, 2015, published in Zhurnal Organicheskoi Khimii, 2015, Vol. 51, No. 5, pp. 650–655.

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Dyachenko, I.V., Dyachenko, V.D. New synthetic approach to substituted 2-alkylsulfanyl-4,6-diaryl(heteryl)-1,4-dihydropyridine-, pyridine-, and thieno[2,3-b]pyridine-3-carbonitriles. Russ J Org Chem 51, 629–635 (2015). https://doi.org/10.1134/S1070428015050073

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  • DOI: https://doi.org/10.1134/S1070428015050073

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