Advertisement

Russian Journal of Organic Chemistry

, Volume 54, Issue 11, pp 1681–1688 | Cite as

Synthesis of 2-Alkylsulfanyl-6-amino-4-aryl-5-cyanonicotinonitriles by Recyclization of 2,6-Diamino-4-aryl-3,5-dicyano-4Н-thiopyrans with Alkyl Halides

  • I. V. Dyachenko
  • V. D. Dyachenko
  • P. V. Dorovatovskii
  • V. N. Khrustalev
  • V. G. NenaydenkoEmail author
Article
  • 1 Downloads

Abstract

2,6-Diamino-4-aryl-3,5-dicyano-4Н-thiopyrans in DMF in the presence of bases recycle into pyridine derivatives. After adding of haloalkanes diverse 2-(alkylsulfanyl)-6-amino-4-aryl-5-cyano-nicotinonitriles are formed.

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

References

  1. 1.
    Rosentreter, U., Kraemer, T., Vaupel, A., Huebsch, W., Diedrichs, N., Krahn, T., Dembowsky, K., and Stasch, J.-P., DE Appl. no. 10110754, 2002; RZhKhim., 2003, no. 03.14-19O.88P.Google Scholar
  2. 2.
    Starosila, S.A., Protopopov, M.V., Dyachenko, I.V., Balanda, A.O., Dyachenko, V.D., and Yarmolyuk, S.M., Zh. Biorg. Khim., 2013, p. 32.Google Scholar
  3. 3.
    Grant, R., Latham, C.J., Thompson, S., and Zhao, L., GB Appl. no. 2388593, 2003; RZhKhim, 2004, no. 04.10-19O.88P.Google Scholar
  4. 4.
    Rosentreter, U., Kraemer, T., Shimada, M., Huebsch, W., Diedrichs, N., Krahn, T., Henninger, K., and Stasch, J.-P., DE Appl. no. 10134481, 2003; RZhKhim., 2003, no. 03.19-19O.91P.Google Scholar
  5. 5.
    Albrecht-Küpper, B.E., Leineweber, K., and Nell, P.G., Purinerg. Signall., 2012, vol. 8, p. 91. doi  https://doi.org/10.1007/s11302-011-9274-3 CrossRefGoogle Scholar
  6. 6.
    Rosentreter, U., Henning, R., Bauser, M., Kraemer, T., Vaupel, A., Huebsch, W., Dembowsky, K., Salecher-Schraufstaetter, O., Stasch, J.-P., Krahn, T., and Perzborn, E., PCT Int. Apll. WO 01 25210; Chem. Abstr., 2001, no. 134, p. 295744e.Google Scholar
  7. 7.
    Dyachenko, V.D. and Litvinov, V.P., Russ. J. Org. Chem., 1998, vol. 34, p. 554.Google Scholar
  8. 8.
    Mohamed, A.M.G.-E., Mohamed, A.A.E., and Adel, A.M.T., Heteroatom Chem., 2007, vol. 18, p. 405.CrossRefGoogle Scholar
  9. 9.
    Fuentes, L., Vaquevo, J.J., del Castillo, J.C., Ardid, M.I., and Soto, J.L., Heterocycles, 1985, vol. 23, p. 93.CrossRefGoogle Scholar
  10. 10.
    Beukers, M.W., Chang, L.C.W., Von Frijtag, D.K.J.K., Mulder-Krieger, T., Spanjersberg, R.F., Brussel, J., and Lizerman, A.P., J. Med. Chem., 2004, vol. 47, p. 3707.CrossRefGoogle Scholar
  11. 11.
    Chang, L.C.W., Frijtag, D.K.J.K., Mulder-Krieger, T., Spanjersberg, R.F., Roering, S.F., Hout, G., Beukers, M.W., Brussel, J., and Lizerman, A.P., J. Med. Chem., 2005, vol. 48, p. 2045.CrossRefGoogle Scholar
  12. 12.
    Evdokimov, N.M., Kireev, A.S., Yakovenko, A.A., Antipin, M.Yu., Magedov, I.V., and Kornienko, A., J. Org. Chem., 2007, vol. 72, p. 3443.CrossRefGoogle Scholar
  13. 13.
    Dyachenko, V.D., Dyachenko, I.V., and Nenaidenko, V.G., Russ. Chem. Rev., 2018, vol. 87, p. 1. doi  https://doi.org/10.1070/RCR4760 CrossRefGoogle Scholar
  14. 14.
    Antipin, I.S., Kazymova, M.A., Kuznetsov, M.A., Vasilyev, A.V., Ishchenko, M.A., Kiryushkin, A.A., Kuznetsova, L.M., Makarenko, S.V., Ostrovskii, V.A., Petrov, M.L., Solod, O.V., Trishin, Yu.G., Yakovlev, I.P., Nenaidenko, V.G., Beloglazkina, E.K., Beletskaya, I.P., Ustynyuk, Yu.A., Solov’ev, P.A., Ivanov, I.V., Malina, E.V., Sivova, N.V., Negrebetskii, V.V., Baukov, Yu.I., Pozharskaya, N.A., Traven’, V.F., Shchekotikhin, A.E., Varlamov, A.V., Borisova, T.N., Lesina, Yu.A., Krasnokutskaya, E.A., Rogozhnikov, S.I., Shurov, S.N., Kustova, T.P., Klyuev, M.V., Khelevina, O.G., Stuzhin, P.A., Fedorov, A.Yu., Gushchin, A.V., Dodonov, V.A., Kolobov, A.V., Shakhtinskii, V.V., Orlov, V.Yu., Kriven’ko, A.P., Fedotova, O.V., Pchelintseva, N.V., Charushin, V.N., Chupakhin, O.N., Klimochkin, Yu.N., Klimochkina, A.Yu., Kuryatnikov, V.N., Malinovskaya, Yu.A., Levina, A.S., Zhuravlev, O.E., Voronchikhina, L.I., Fisyuk, A.S., Aksenov, A.V., Aksenov, N.A., and Aksenova, I.V., Russ. J. Org. Chem., 2017, vol. 53, p. 1275. doi  https://doi.org/10.1134/S1070428017090019 CrossRefGoogle Scholar
  15. 15.
    Konovalov, A.I., Antipin, I.S., Burilov, V.A., Madzhidov, T.I., Kurbangalieva, A.R., Nemtarev, A.V., Solovieva, S.E., Stoikov, I.I., Mamedov, V.A., Zakharova, L.Ya., Gavrilova, E.L., Sinyashin, O.G., Balova, I.A., Vasilyev, A.V., Zenkevich, I.G., Krasavin, M.Yu., Kuznetsov, M.A., Molchanov, A.P., Novikov, M.S., Nikolaev, V.A., Rodina, L.L., Khlebnikov, A.F., Beletskaya, I.P., Vatsadze, S.Z., Gromov, S.P., Zyk, N.V., Lebedev, A.T., Lemenovskii, D.A., Petrosyan, V.S., Nenaidenko, V.G., Negrebetskii, V.V., Baukov, Yu.I., Shmigol’, T.A., Korlyukov, A.A., Tikhomirov, A.S., Shchekotikhin, A.E., Traven’, V.F., Voskresenskii, L.G., Zubkov, F.I., Golubchikov, O.A., Semeikin, A.S., Berezin, D.B., Stuzhin, P.A., Filimonov, V.D., Krasnokutskaya, E.A., Fedorov, A.Yu., Nyuchev, A.V., Orlov, V.Yu., Begunov, R.S., Rusakov, A.I., Kolobov, A.V., Kofanov, E.R., Fedotova, O.V., Egorova, A.Yu., Charushin, V.N., Chupakhin, O.N., Klimochkin, Yu.N., Osyanin, V.A., Reznikov, A.N., Fisyuk, A.S., Sagitullina, G.P., Aksenov, A.V., Aksenov, N.A., Grachev, M.K., Maslennikova, V.I., Koroteev, M.P., Brel’, A.K., Lisina, S.V., Medvedeva, S.M., Shikhaliev, Kh.S., Suboch, G.A., Tovbis, M.S., Mironovich, L.M., Ivanov, S.M., Kurbatov, S.V., Kletskii, M.E., Burov, O.N., Kobrakov, K.I., and Kuznetsov, D.N., Russ. J. Org. Chem., 2018, vol. 54, p. 157. doi  https://doi.org/10.1134/S107042801802001X CrossRefGoogle Scholar
  16. 16.
    Sharanin, Yu.A., Shestopalov, A.M., Nesterov, V.N., Melenchuk, S.N., Promonenkov, V.K., Shklover, V.E., Struchkov, Yu.T., and Litvinov, V.P., Zh. Org. Khim., 1989, vol. 25, p. 1323.Google Scholar
  17. 17.
    Dyachenko, V.D., Zh. Org. Farm. Khim., 2007, p. 14.Google Scholar
  18. 18.
    Dyachenko, V.D., Krivokolysko, S.G., Sharanin, Yu.A., and Litvinov, V.P., Russ. J. Org. Chem., 1997, vol. 33, p. 1014.Google Scholar
  19. 19.
    Dyachenko, V.D. and Karpov, E.N., Zh. Org. Farm. Khim., 2007, p. 14.Google Scholar
  20. 20.
    Dyachenko, V.D., Krivokolysko, S.G., Sharanin, Yu.A., and Litvinov, V.P., Chem. Heterocycl. Compd., 1997, vol. 33, p. 793. doi  https://doi.org/10.1007/BF02253028 CrossRefGoogle Scholar
  21. 21.
    Rodinovskaya, L.A., Sharanin, Yu.A., Litvinov, V.P., Shestopalov, A.M., Promonenkov, V.K., Zolotarev, E.M., Mortikov, V.Yu., Zh. Org. Khim., 1985, vol. 21, p. 2439.Google Scholar
  22. 22.
    Sharanin, Yu.A., Shestopalov, A.M., Promonenkov, V.K., and Rodinovskaya, L.A., Zh. Org. Khim., 1984, vol. 20, p. 2432.Google Scholar
  23. 23.
    Sharanin, Yu.A., Promonenkov, V.K., Shestopalov, A.M., Nesterov, V.N., Melenchuk, S.N., Shklover, V.E., and Struchkov, Yu.T., Zh. Org. Khim., 1989, vol. 25, p. 622.Google Scholar
  24. 24.
    Elnagdi, M., Horb, A.F.A., Elghandour, A.H.H., Hussien, A.H.M., and Metwally, S.A.M., Gazz. Chim. Ital., 1992, vol. 122, p. 299.Google Scholar
  25. 25.
    Battye, T.G., Kontogiannis, L., Johnson, O., Powell, H.R., and Leslie, A.G.W., Acta Cryst., 2011, vol. D67, p. 271. doi  https://doi.org/10.1107/S0907444910048675 Google Scholar
  26. 26.
    Evans, P., Acta Cryst., 2006, vol. D62, p. 72. doi  https://doi.org/10.1107/S0907444905036693 Google Scholar
  27. 27.
    Sheldrick, G.M., Acta Cryst., 2015, vol. C71, p. 3.Google Scholar
  28. 28.
    Dyachenko, V.D. and Dyachenko, A.D., Russ. J. Org. Chem., 2007, vol. 43, p. 280. doi  https://doi.org/10.1134/S1070428007020212 CrossRefGoogle Scholar

Copyright information

© Pleiades Publishing, Ltd. 2018

Authors and Affiliations

  • I. V. Dyachenko
    • 1
  • V. D. Dyachenko
    • 1
  • P. V. Dorovatovskii
    • 2
  • V. N. Khrustalev
    • 2
    • 3
  • V. G. Nenaydenko
    • 4
    Email author
  1. 1.Taras Shevchenko Lugansk State UniversityLuganskUkraine
  2. 2.National Research Center “Kurchatov Institute”MoscowRussia
  3. 3.Peoples’ Friendship University of RussiaMoscowRussia
  4. 4.Moscow State UniversityMoscowRussia

Personalised recommendations