Advertisement

Russian Journal of General Chemistry

, Volume 89, Issue 1, pp 19–24 | Cite as

Reaction of 5-Amino-3-(cyanomethyl)-1H-pyrazole-4-carbonitrile with Hydroxycyclohexanones

  • A. M. Semenova
  • R. V. Oganesyan
  • V. V. DotsenkoEmail author
  • E. A. Chigorina
  • N. A. Aksenov
  • I. V. Aksenova
  • E. E. Netrebae
Article
  • 11 Downloads

Abstract

The reaction of 5-amino-3-(cyanomethyl)-1H-pyrazole-4-carbonitrile with 3-aryl-5-hydroxy-5- methyl-2,4-di(ethoxycarbonyl)cyclohexanones in acetic acid furnished previously unknown 4,5,6,7,8,9-hexahydropyrazolo[1,5-a]quinazoline derivatives.

Keywords

β-cycloketols aminopyrazole cyclocondensation pyrazolo[1,5-a]quinazoline 

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

References

  1. 1.
    Kriven’ko, A.P. and Sorokin, V.V., Zameshcennye tsyklogeksanolones (Substituted Cyclohexanolones), Saratov: Saratovsk. Univ., 1999, p. 20.Google Scholar
  2. 2.
    Ismiev, A.I., Magerramov, A.M., Sukach, V.A., and Vovk, M.V., Zh. Org. Farm. Khim., 2016, vol. 14, no. 4 (56), p. 16.Google Scholar
  3. 3.
    Ozols, A.I., Pelcher, Yu.Ê., Kalme, Z.A., Popelis, Yu.Yu., Turovskis, I.V., and Duburs, G.Ya., Chem. Heterocycl. Compd., 1996, vol. 32, no. 1, p. 52. doi  https://doi.org/10.1007/BF01169354 CrossRefGoogle Scholar
  4. 4.
    Dyachenko, V.D., Sukach, S.M., and Dyachenko, A.D., Chem. Heterocycl. Compd., 2015, vol. 51, no. 1, p. 51. doi  https://doi.org/10.1007/s10593-015-1658-9 CrossRefGoogle Scholar
  5. 5.
    Dyachenko, V.D. and Karpov, E.N., Russ. J. Org. Chem., 2014, vol. 50, no. 12, p. 1787. doi  https://doi.org/10.1134/S1070428014120136 CrossRefGoogle Scholar
  6. 6.
    Sukach, S.M. and Dyachenko, V.D., Russ. J. Org. Chem., 2015, vol. 51, no. 7, p. 1020. doi  https://doi.org/10.1134/S1070428015070210 CrossRefGoogle Scholar
  7. 7.
    Dyachenko, V.D. and Sukach, S.M., Chem. Heterocycl. Compd., 2010, vol. 46, no. 12, p. 1467. doi  https://doi.org/10.1007/s10593-011-0693-4 CrossRefGoogle Scholar
  8. 8.
    Gein, V.L., Nosova, N.V., Potemkin, K.D., Aliev, Z.G., and Kriven’ko, A.P., Russ. J. Org. Chem., 2005, vol. 41, no. 7, p. 1016. doi  https://doi.org/10.1007/s11178-005-0287-7 CrossRefGoogle Scholar
  9. 9.
    Sorokin, V.V., Grigoryev, A.V., Ramazanov, A.K., and Krivenko, A.P., Chem. Heterocycl. Compd., 1999, vol. 35, no. 6, p. 671. doi  https://doi.org/10.1007/BF02251624 CrossRefGoogle Scholar
  10. 10.
    Smirnova, N.O., Plotnikov, O.P., Vinogradova, N.A., Sorokin, V.V., and Kriven’ko, A.P., Pharm. Chem. J., 1995, vol. 29, no. 1, p. 49. doi  https://doi.org/10.1007/BF02219464 CrossRefGoogle Scholar
  11. 11.
    Poplevina, N.V., Kuznetsova, A.A., and Krivenko, A.P., Chem. Heterocycl. Compd., 2010, vol. 46, no. 9, p. 1148. doi  https://doi.org/10.1007/s10593-010-0644-5 CrossRefGoogle Scholar
  12. 12.
    Dyachenko, V.D. and Sukach, S.M., Russ. J. Gen. Chem., 2012, vol. 82, no. 2, p. 305. doi  https://doi.org/10.1134/S1070363212020211 CrossRefGoogle Scholar
  13. 13.
    Anwar, H.F. and Elnagdi, M.H., Arkivoc, 2009, p. 198. doi  https://doi.org/10.3998/ark.5550190.0010.107 Google Scholar
  14. 14.
    Abu Elmaati, T.M. and El-Taweel, F.M., J. Heterocycl. Chem., 2004, vol. 41, no. 2, p. 109. doi  https://doi.org/10.1002/jhet.5570410201 CrossRefGoogle Scholar
  15. 15.
    Etman, H.A., Sadek, M.G., and Khalil, A.G.M., Res. J. Pharm. Biol. Chem. Sci., 2015, vol. 6, no. 2, p. 247.Google Scholar
  16. 16.
    Dotsenko, V.V., Ismiev, A.I., Khrustaleva, A.N., Frolov, K.A., Krivokolysko, S.G., Chigorina, E.A., Snizhko, A.P., Gromenko, V.M., Bushmarinov, I.S., Askerov, R.K., Pekhtereva, T.M., Suykov, S.Yu., Papayanina, E.S., Mazepa, A.V., and Magerramov, A.M., Chem. Heterocycl. Compd., 2016, vol. 52, no. 7, p. 473. doi  https://doi.org/10.1007/s10593-016-1918-3 CrossRefGoogle Scholar
  17. 17.
    Dotsenko, V.V., Krivokolysko, S.G., Chernega, A.N., and Litvinov, V.P., Russ. Chem. Bull., 2003, vol. 52, no. 4, p. 969. doi  https://doi.org/10.1023/A:1024420930528 CrossRefGoogle Scholar
  18. 18.
    Tverdokhleb, N.M., Khoroshilov, G.E., and Dotsenko, V.V., Tetrahedron Lett., 2014, vol. 55, p. 6593. doi  https://doi.org/10.1016/j.tetlet.2014.10.046 CrossRefGoogle Scholar
  19. 19.
    Dotsenko, V.V., Chigorina, E.A., and Krivokolysko, S.G., Chem. Heterocycl. Compd., 2017, vol. 53, no. 5, p. 626. doi  https://doi.org/10.1007/s10593-017-2103-z CrossRefGoogle Scholar
  20. 20.
    Ledenyova, I.V., Didenko, V.V., Dotsenko, V.V., and Shikhaliev, K.S., Tetrahedron Lett., 2014, vol. 55, no. 6, p. 1239. doi  https://doi.org/10.1016/j.tetlet.2014.01.010 CrossRefGoogle Scholar
  21. 21.
    Kolosov, M.A., Beloborodov, D.A., Orlov, V.D., and Dotsenko, V.V., New J. Chem., 2016, vol. 40, no. 9, p. 7573. doi  https://doi.org/10.1039/c6nj00336b CrossRefGoogle Scholar
  22. 22.
    Carboni, R.A., Coffman, D.D., and Howard, E.G., J. Am. Chem. Soc., 1958, vol. 80, no. 11, p. 2838. doi  https://doi.org/10.1021/ja01544a061 CrossRefGoogle Scholar
  23. 23.
    Metwally, N.H., Abdallah, M.A., and Almabrook, S.A., J. Heterocycl. Chem., 2017, vol. 54, no. 1, p. 347. doi  https://doi.org/10.1002/jhet.2590 CrossRefGoogle Scholar
  24. 24.
    Ragab, E.A., Metwally, N.H., and Mohamed, M.S., Synth. Commun., 2017, vol. 47, no. 2, p. 148. doi  https://doi.org/10.1080/00397911.2016.1257722 CrossRefGoogle Scholar
  25. 25.
    Elkholy, A., Al-Qala, F., and Elnagdi, M.H., Arkivoc, 2008, p. 124.Google Scholar
  26. 26.
    Metwally, N.H. and Mohamed, M.S., Synth. Commun., 2018, vol. 48, no. 7, p. 721. doi  https://doi.org/10.1080/00397911.2017.1399208 CrossRefGoogle Scholar
  27. 27.
    Garg, M., Chauhan, M., Singh, P.K., Alex, J.M., and Kumar, R., Eur. J. Med. Chem., 2015, vol. 97, p. 444. doi  https://doi.org/10.1016/j.ejmech.2014.11.051 CrossRefGoogle Scholar
  28. 28.
    Yet, L., Privileged Structures in Drug Discovery: Medicinal Chemistry and Synthesis, New York: John Wiley & Sons, 2018, p. 9.CrossRefGoogle Scholar
  29. 29.
    Elnagdi, M.H., Sallam, M.M.M., and Ilias, M.A.M., Helv. Chim. Acta, 1975, vol. 58, no. 7, p. 1944. doi  https://doi.org/10.1002/hlca.19750580710 CrossRefGoogle Scholar
  30. 30.
    Zayed, E.M., Ghozlan, S.A.S., and Ibrahim, A.A.H., Monatsh. Chem., 1984, vol. 115, no. 4, p. 431. doi  https://doi.org/10.1007/BF00810004 CrossRefGoogle Scholar
  31. 31.
    Finar, I.L., J. Chem. Soc., 1961, no. 2, p. 674. doi  https://doi.org/10.1039/JR9610000674 CrossRefGoogle Scholar

Copyright information

© Pleiades Publishing, Ltd. 2019

Authors and Affiliations

  • A. M. Semenova
    • 1
    • 2
  • R. V. Oganesyan
    • 1
  • V. V. Dotsenko
    • 1
    • 3
    Email author
  • E. A. Chigorina
    • 4
  • N. A. Aksenov
    • 3
  • I. V. Aksenova
    • 3
  • E. E. Netrebae
    • 5
  1. 1.Kuban State UniversityKrasnodarRussia
  2. 2.North Caucasian State Humanitarian and Technological AcademyMedical InstituteCherkesskRussia
  3. 3.North Caucasus Federal UniversityStavropolRussia
  4. 4.National Research Center “Kurchatov Institute”–IREAMoscowRussia
  5. 5.Taurida Academy of V.I. Vernadsky Crimean Federal UniversitySimferopolRussia

Personalised recommendations