Russian Journal of General Chemistry

, Volume 88, Issue 4, pp 682–688 | Cite as

A New Approach to the Synthesis of Functional Derivatives of 3-(4-Pyridinyl)-1H-indole and 4-(1H-Indol-3-yl)thieno[2,3-b]pyridine

  • V. V. Dotsenko
  • S. G. Krivokolysko
  • B. S. Krivokolysko
  • K. A. Frolov


Sequential reaction of indole-3-carbaldehyde with cyanothioacetamide and KOH led to the formation of potassium 6-amino-4-(1H-indol-3-yl)-3,5-dicyanopyridine-2-thiolate. S-Alkylation of the latter afforded new functional derivatives of 3-(pyridine-4-yl)-1H-indole and 4-(1H-indol-3-yl)-thieno[2,3-b]pyridine.


cyanothioacetamide 3-(pyridine-4-yl)-1H-indoles 6-amino-3,5-dicyanopyridine-2-thiolate Thorpe–Ziegler cyclization thieno[2,3-b]pyridines 


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This work was supported by the Ministry of Education and Science of the Russian Federation (project no. 4.5547.2017/BCh) using the equipment of the Ecological and Analytical Center of the Kuban State University (unique identifier RFMEFI59317X0008).


  1. 1.
    Dotsenko, V.V., Krivokolysko, S.G., and Litvinov, V.P., Monatsh. Chem., 2008, vol. 139, p. 271. doi 10.1007/s00706-007-0784-1CrossRefGoogle Scholar
  2. 2.
    Dotsenko, V.V., Krivokolysko, S.G., Chernega, A.N., and Litvinov, V.P., Russ. Chem. Bull., 2002, vol. 51, p. 1556. doi 10.1023/A:1020939712830CrossRefGoogle Scholar
  3. 3.
    Frolov, K.A., Dotsenko, V.V., and Krivokolysko, S.G., Chem. Heterocycl. Compd., 2013, vol. 49, p. 1301. doi 10.1007/s10593-013-1379-xCrossRefGoogle Scholar
  4. 4.
    Dotsenko, V.V., Chigorina, E.A., Papaianina, E.S., Frolov, K.A., and Krivokolysko, S.G., Macroheterocycles, 2015, vol. 8, p. 310. doi 10.6060/mhc150870dCrossRefGoogle Scholar
  5. 5.
    Dotsenko, V.V., Krivokolysko, S.G., Polovinko, V.V., and Litvinov, V.P., Chem. Heterocycl. Compd., 2012, vol. 48, p. 309. doi 10.1007/s10593-012-0991-5CrossRefGoogle Scholar
  6. 6.
    Dotsenko, V.V. and Krivokolysko, S.G., Chem. Heterocycl. Compd., 2012, vol. 48, p. 1568. doi 10.1007/s10593-013-1176-6CrossRefGoogle Scholar
  7. 7.
    Dotsenko, V.V., Frolov, K.A., Krivokolysko, S.G., and Polovinko, V.V., Chem. Heterocycl. Compd., 2013, vol. 49, p. 440. doi 10.1007/s10593-013-1266-5CrossRefGoogle Scholar
  8. 8.
    Kolotaev, A.V., Belenґkii, L.I., Kononikhin, A.S., and Krayushkin, M.M., Russ. Chem. Bull., 2006, vol. 55, p. 892. doi 10.1007/s11172-006-0348-2CrossRefGoogle Scholar
  9. 9.
    Vecchione, M.K., Sun, A.X., and Seidel, D., Chem. Sci., 2011, vol. 2, p. 2178. doi 10.1039/C1SC00506ECrossRefGoogle Scholar
  10. 10.
    Lee, S. and Park, S.B., Org. Lett., 2009, vol. 11, p. 5214. doi 10.1021/ol902147uCrossRefPubMedGoogle Scholar
  11. 11.
    Lee, S., Jo, A., and Park, S.B., Med. Chem. Commun., 2013, vol. 4, p. 228. doi 10.1039/c2md20169kCrossRefGoogle Scholar
  12. 12.
    Knepper, I., Iaroshenko, V.O., Vilches-Herrera, M., Domke, L., Mkrtchyan, S., Zahid, M., Villinger, A., and Langer, P., Tetrahedron, 2011, vol. 67, no. 29, p. 5293. doi 10.1016/j.tet.2011.05.037CrossRefGoogle Scholar
  13. 13.
    Liu, C., Zhou, L., Jiang, D., and Gu, Y., Asian J. Org. Chem., 2016, vol. 5, no. 3, p. 367. doi 10.1002/ajoc.201500497CrossRefGoogle Scholar
  14. 14.
  15. 15.
    Evdokimov, N.M., Magedov, I.V., Kireev, A.S., and Kornienko, A., Org. Lett., 2006, vol. 8, no. 5, p. 899. doi 10.1021/ol052994+CrossRefPubMedGoogle Scholar
  16. 16.
    Brandt, W., Mologni, L., Preu, L., Lemcke, T., Gambacorti-Passerini, C., and Kunick, C., Eur. J. Med. Chem., 2010, vol. 45, p. 2919. doi 10.1016/j.ejmech.2010.03.017CrossRefPubMedGoogle Scholar
  17. 17.
    Chang, L.C.W., von Frijtag Drabbe Künzel, J.K., Mulder-Krieger, T., Spanjersberg, R.F., Roerink, S.F., van den Hout, G., Beukers, M.W., Brussee, J., and Ijzerman, A.P., J. Med. Chem., 2005, vol. 48, p. 2045. doi 10.1021/jm049597+CrossRefPubMedGoogle Scholar
  18. 18.
    May, B.C.H., Zorn, J.A., Witkop, J., Sherrill, J., Wallace, A.C., Legname, G., Prusiner, S.B., and Cohen, F.E., J. Med. Chem., 2007, vol. 50, no. 1, p. 65. doi 10.1021/jm061045zCrossRefPubMedGoogle Scholar
  19. 19.
    Louvel, J., Guo, D., Soethoudt, M., Mocking, T.A.M., Lenselink, E.B., Mulder-Krieger, T., Heitman, L.H., and Ijzerman, A.P., Eur. J. Med. Chem., 2015, vol. 101, p. 681. doi 10.1016/j.ejmech.2015.07.023CrossRefPubMedGoogle Scholar
  20. 20.
    Rosentreter, U., Kramer, T., Vaupel, A., Hubsch, W., Diedrichs, N., Krahn, T., Dembowsky, K., Stasch, J.P., and Shimada, M., US Patent 2004102626, 2004.Google Scholar
  21. 21.
    Krahn, T., Thielemann, W., Rosentreter, U., Diedrichs, N., and Kraemer, T., WO Patent 2006002823, 2006.Google Scholar
  22. 22.
    Krahn, T., Kraemer, T., Rosentreter, U., Downey, J.M., and Solenkova, N., US Patent 2009221649, 2009.Google Scholar
  23. 23.
    Rosentreter, U., Kramer, T., Vaupel, A., Hubsch, W., Diedrichs, N., Krahn, T., Dembowsky, K., Stasch, J.P., and Shimada, M., US Patent 20040110946, 2004.Google Scholar
  24. 24.
    Litvinov, V.P., Promonenkov, V.K., Sharanin, Yu.A., and Shestopalov, A.M., Itogi Nauki i Tekhniki VINITI, Ser. Org. Khim., Moscow: VINITI, 1989, vol. 17, p. 72.Google Scholar
  25. 25.
    Litvinov, V.P., Rodinovskaya, L.A., Sharanin, Yu.A., Shestopalov, A.M., and Senning, A., Sulfur Rep., 1992, vol. 13, p. 1. doi 10.1080/01961779208048951CrossRefGoogle Scholar
  26. 26.
    Litvinov, V.P., Krivokolysko, S.G., and Dyachenko, V.D., Chem. Heterocycl. Compd., 1999, vol. 35, no. 5, p. 509. doi 10.1007/BF02324634CrossRefGoogle Scholar
  27. 27.
    Beukers, M.W., Chang, L.C.W., von Frijtag Drabbe Künzel, J.K., Mulder-Krieger, T., Spanjersberg, R.F., Brussee, J., and Ijzerman, A.P., J. Med. Chem., 2004, vol. 47, no. 15, p. 3707. doi 10.1021/jm049947sCrossRefPubMedGoogle Scholar
  28. 28.
    Kambe, S., Saito, K., Sakurai, A., and Midorikawa, H., Synthesis, 1981, no. 7, p. 531. doi 10.1055/s-1981-29513CrossRefGoogle Scholar
  29. 29.
    Bakhite, E.A.G., Phosphorus, Sulfur, Silicon, Relat. Elem., 2003, vol. 178, p. 929. doi 10.1080/10426500390208820CrossRefGoogle Scholar
  30. 30.
    Litvinov, V.P., Dotsenko, V.V., and Krivokolysko, S.G., Adv. Heterocycl. Chem., 2007, vol. 93, p. 117. doi 10.1016/S0065-2725(06)93003-7CrossRefGoogle Scholar
  31. 31.
    Litvinov, V.P., Dotsenko, V.V., and Krivokolysko, S.G., Russ. Chem. Bull., 2005, vol. 54, no. 4, p. 864. doi 10.1007/s11172-005-0333-1CrossRefGoogle Scholar
  32. 32.
    Litvinov, V.P., Dotsenko, V.V., and Krivokolysko, S.G., Khimiya tienopiridinov i rodstvennykh sistem (Chemistry of Thienopyridines and Related Compounds), Moscow: Nauka, 2006.Google Scholar
  33. 33.
    Thirumurugan, P., Mahalaxmi, S., and Perumal, P.T., J. Chem. Sci., 2010, vol. 122, no. 6, p. 819. CrossRefGoogle Scholar
  34. 34.
    Eggenweiler, H.-M. and Wolf, M., WO Patent 2006092202, 2006.Google Scholar
  35. 35.
    Eggenweiler, H.-M. and Wolf, M., US Patent 20100048558, 2010.Google Scholar
  36. 36.
    Fugel, W., Oberholzer, A.E., Gschloessl, B., Dzikowski, R., Pressburger, N., Preu, L., Pearl, L.H., Baratte, B., Ratin, M., Okun, I., Doerig, C., Kruggel, S., Lemcke, T., Meijer, L., and Kunick, C., J. Med. Chem., 2013, vol. 56, no. 1, p. 264. doi 10.1021/jm301575nCrossRefPubMedGoogle Scholar
  37. 37.
    Dyachenko, V.D. and Dyachenko, A.D., Russ. J. Org. Chem., 2006, vol. 42, no. 7, p. 1091. doi 10.1134/S1070428006070311CrossRefGoogle Scholar

Copyright information

© Pleiades Publishing, Ltd. 2018

Authors and Affiliations

  • V. V. Dotsenko
    • 1
    • 2
  • S. G. Krivokolysko
    • 1
  • B. S. Krivokolysko
    • 1
  • K. A. Frolov
    • 1
  1. 1.Kuban State UniversityKrasnodarRussia
  2. 2.North-Caucasus Federal UniversityStavropolRussia

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