Skip to main content
SpringerLink
Log in

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

  • Published:
Russian Journal of General Chemistry Aims and scope Submit manuscript

Abstract

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.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Similar content being viewed by others

References

  1. Dotsenko, V.V., Krivokolysko, S.G., and Litvinov, V.P., Monatsh. Chem., 2008, vol. 139, p. 271. doi 10.1007/s00706-007-0784-1

    Article  CAS  Google Scholar 

  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:1020939712830

    Article  CAS  Google Scholar 

  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-x

    Article  CAS  Google Scholar 

  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/mhc150870d

    Article  CAS  Google Scholar 

  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/s10593-012-0991-5

    Article  CAS  Google Scholar 

  6. Dotsenko, V.V. and Krivokolysko, S.G., Chem. Heterocycl. Compd., 2012, vol. 48, p. 1568. doi 10.1007/s10593-013-1176-6

    Article  CAS  Google Scholar 

  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/s10593-013-1266-5

    Article  CAS  Google Scholar 

  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/s11172-006-0348-2

    Article  CAS  Google Scholar 

  9. Vecchione, M.K., Sun, A.X., and Seidel, D., Chem. Sci., 2011, vol. 2, p. 2178. doi 10.1039/C1SC00506E

    Article  CAS  Google Scholar 

  10. Lee, S. and Park, S.B., Org. Lett., 2009, vol. 11, p. 5214. doi 10.1021/ol902147u

    Article  CAS  PubMed  Google Scholar 

  11. Lee, S., Jo, A., and Park, S.B., Med. Chem. Commun., 2013, vol. 4, p. 228. doi 10.1039/c2md20169k

    Article  CAS  Google Scholar 

  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.2011.05.037

    Article  CAS  Google Scholar 

  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.201500497

    Article  CAS  Google Scholar 

  14. Vilches-Herrera, M., Candidate Dissert. (Chem.), Rostock, 2012, p. 6. http://rosdok.uni-rostock.de/file/rosdok_derivate_0000005017/Dissertation_Vilches-Herrera_2013.pdf.

    Google Scholar 

  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+

    Article  CAS  PubMed  Google Scholar 

  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.2010.03.017

    Article  CAS  PubMed  Google Scholar 

  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+

    Article  CAS  PubMed  Google Scholar 

  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/jm061045z

    Article  CAS  PubMed  Google Scholar 

  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.2015.07.023

    Article  CAS  PubMed  Google Scholar 

  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. Krahn, T., Thielemann, W., Rosentreter, U., Diedrichs, N., and Kraemer, T., WO Patent 2006002823, 2006.

    Google Scholar 

  22. Krahn, T., Kraemer, T., Rosentreter, U., Downey, J.M., and Solenkova, N., US Patent 2009221649, 2009.

    Google Scholar 

  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. 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. Litvinov, V.P., Rodinovskaya, L.A., Sharanin, Yu.A., Shestopalov, A.M., and Senning, A., Sulfur Rep., 1992, vol. 13, p. 1. doi 10.1080/01961779208048951

    Article  CAS  Google Scholar 

  26. Litvinov, V.P., Krivokolysko, S.G., and Dyachenko, V.D., Chem. Heterocycl. Compd., 1999, vol. 35, no. 5, p. 509. doi 10.1007/BF02324634

    Article  CAS  Google Scholar 

  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/jm049947s

    Article  CAS  PubMed  Google Scholar 

  28. Kambe, S., Saito, K., Sakurai, A., and Midorikawa, H., Synthesis, 1981, no. 7, p. 531. doi 10.1055/s-1981-29513

    Article  Google Scholar 

  29. Bakhite, E.A.G., Phosphorus, Sulfur, Silicon, Relat. Elem., 2003, vol. 178, p. 929. doi 10.1080/10426500390208820

    Article  CAS  Google Scholar 

  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)93003-7

    Article  CAS  Google Scholar 

  31. Litvinov, V.P., Dotsenko, V.V., and Krivokolysko, S.G., Russ. Chem. Bull., 2005, vol. 54, no. 4, p. 864. doi 10.1007/s11172-005-0333-1

    Article  CAS  Google Scholar 

  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. Thirumurugan, P., Mahalaxmi, S., and Perumal, P.T., J. Chem. Sci., 2010, vol. 122, no. 6, p. 819. http://www.ias.ac.in/article/fulltext/jcsc/122/06/0819-0832.

    Article  CAS  Google Scholar 

  34. Eggenweiler, H.-M. and Wolf, M., WO Patent 2006092202, 2006.

    Google Scholar 

  35. Eggenweiler, H.-M. and Wolf, M., US Patent 20100048558, 2010.

    Google Scholar 

  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/jm301575n

    Article  CAS  PubMed  Google Scholar 

  37. Dyachenko, V.D. and Dyachenko, A.D., Russ. J. Org. Chem., 2006, vol. 42, no. 7, p. 1091. doi 10.1134/S1070428006070311

    Article  CAS  Google Scholar 

Download references

Acknowledgments

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).

Author information

Authors and Affiliations

  1. Kuban State University, ul. Stavropol’skaya 149, Krasnodar, 350040, Russia

    V. V. Dotsenko, S. G. Krivokolysko, B. S. Krivokolysko & K. A. Frolov

  2. North-Caucasus Federal University, Stavropol, Russia

    V. V. Dotsenko

Authors
  1. V. V. Dotsenko
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. S. G. Krivokolysko
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. B. S. Krivokolysko
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. K. A. Frolov
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to V. V. Dotsenko.

Additional information

Original Russian Text © V.V. Dotsenko, S.G. Krivokolysko, B.S. Krivokolysko, K.A. Frolov, 2018, published in Zhurnal Obshchei Khimii, 2018, Vol. 88, No. 4, pp. 599–605.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Dotsenko, V.V., Krivokolysko, S.G., Krivokolysko, B.S. et al. 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. Russ J Gen Chem 88, 682–688 (2018). https://doi.org/10.1134/S1070363218040114

Download citation

  • Received:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1134/S1070363218040114

Keywords

Search

Navigation