Skip to main content
SpringerLink
Log in

Synthesis of Azaheterocyclic Cymantrene Derivatives

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

Abstract

The reduction of acetylcymantrene with sodium tetrahydridoborate gave cymantrenylethanol which was acylated with 4,5-dichloroisothiazole- and 5-(4-methylphenyl)isoxazole-3-carbonyl chlorides to obtain esters containing a 1,2-thia(oxa)zole fragment. The condensation of acetylcymantrene with 5-arylisoxazole-3- carbaldehydes, (5-arylisoxazol-3-yl)methoxybenzaldehydes (Ar = Ph, 4-Tol), and 4,5-dichloroisothiazole-3- carbaldehyde afforded the corresponding (E)-3-(azol-3-yl)-1-cymantrenylprop-2-en-1-ones. The resulting α,β- unsaturated ketones reacted with semicarbazide hydrochloride and thiosemicarbazide to produce substituted 4,5-dihydro-1H-pyrazole-1-carboxamides and -1-carbothioamides, and their reaction with hydroxylamine hydrochloride led to the formation of 4,5-dihydroisoxazoles containing cymantrene and 1,2-azole fragments. Heterocyclization of azolylcymantrenylpropenones with guanidine gave 2-aminopyrimidine derivatives, and dihydropyrimidine-2-thiones were obtained by their reaction with thiourea.

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. Ginzburg, A.G., Russ. Chem. Rev., 2009, vol. 78, p.195.

    Article  CAS  Google Scholar 

  2. Glans, L., Hu, W., Jöst, Ch., de Kock, C., Smith, P.J., Haukka, M., Bruhn, H., Schatzschneider, U., and Nordlander, E., Dalton Trans., 2012, vol. 41, p. 6443.

    Article  CAS  PubMed  Google Scholar 

  3. N’Dongo, P.H.W., Ott, I., Gust, R., and Schatzschneider, U., J. Organomet. Chem., 2009, vol. 694, p.823.

    Article  CAS  Google Scholar 

  4. N’Dongo, P.H.W., Neundorf, I., Merz, K., and Schatzschneider, U., J. Inorg. Biochem., 2008, vol. 102, p. 2114.

    Article  CAS  Google Scholar 

  5. Biot, Ch., Castro, W., Botté, C.Y., and Navarro, M., Dalton Trans., 2012, vol. 41, p. 6335.

    Article  CAS  PubMed  Google Scholar 

  6. Wenzel, M., Patra, M., Helmut, Ch., Senges, R., Ott, I., Stepanek, J.J., Pinto, A., Prochnow, P., Vuong, C., Langklotz, S., Metzler-Nolte, N., and Bandow, J.E., ACS Chem. Biol., 2013, vol. 8, p. 1442.

    Article  CAS  PubMed  Google Scholar 

  7. Splith, K., Hu, W., Schatzschneider, U., Gust, R., Ott, I., Onambele, L.A., Prokop, A., and Neundorf, I., Bioconjugate Chem., 2010, vol. 21, p. 1288.

    Article  CAS  Google Scholar 

  8. Dallagi, T., Saidi, M., Vessières, A., Huché, M., Jaouen, G., and Top, S., J. Organomet. Chem., 2013, vol. 734, p.69.

    Article  CAS  Google Scholar 

  9. Koroleva, E.V., Gusak, K.N., and Ignatovich, Zh.V., Russ. Chem. Rev., 2010, vol. 79, p.655.

    Article  CAS  Google Scholar 

  10. Al-Issa, S.A., Saudi Pharm. J., 2013, vol. 21, p.305.

    Article  CAS  PubMed  Google Scholar 

  11. Korablina, D.D., Vorozhtsov, N.I., Sviridova, L.A., Kalenikova, E.I., and Medvedev, O.S., Pharm. Chem. J., 2016, vol. 50, no. 5, p.281.

    Article  CAS  Google Scholar 

  12. Kulchitsky, V.A., Potkin, V.I., Zubenko, Yu.S., Chernov, A.N., Talabaev, M.V., Demidchik, Y.E., Petkevich, S.K., Kazbanov, V.V., Gurinovich, T.A., Roeva, M.O., Grigoriev, D.G., Kletskov, A.V., and Kalunov, V.N., Med. Chem. (Sharjah, UAE), 2012, vol. 8, p.22.

    CAS  Google Scholar 

  13. Potkin, V.I., Kletskov, A.V., Petkevich, S.K., Pashkevich, S.G., Kazbanov, V.V., Denisov, A.A., and Kulchitsky, V.A., Heterocyclic Lett., 2015, vol. 5, no. 1, p.11.

    Google Scholar 

  14. Bumagin, N.A., Zelenkovskii, V.M., Kletskov, A.V., Petkevich, S.K., Dikusar, E.A., and Potkin, V.I., Russ. J. Gen. Chem., 2016, vol. 86, p.68.

    Article  CAS  Google Scholar 

  15. Potkin, V.I., Petkevich, S.K., Kletskov, A.V., Dikusar, E.A., Zubenko, Yu.S., Zhukovskaya, N.A., Kazbanov, V.V., and Pashkevich, S.G., Russ. J. Org. Chem., 2013, vol. 49, p. 1523.

    Article  CAS  Google Scholar 

  16. Potkin, V.I., Bumagin, N.A., Petkevich, S.K., Dikusar, E.A., Semenova, E.A., Kurman, P.V., Zolotar’, R.M., Pashkevich, S.G., Gurinovich, T.A., and Kul’chitskii, V.A., Russ. J. Org. Chem., 2015, vol. 51, p. 1119.

    Article  CAS  Google Scholar 

  17. Chebanov, V.A. and Desenko, S.M., Curr. Org. Chem., 2006, vol. 10, p.297.

    Article  CAS  Google Scholar 

  18. Gouhar, R.S. and Youns, M., Res. J. Pharm. Biol. Chem. Sci., 2014, vol. 5, p.680.

    Google Scholar 

  19. Varga, L., Nagy, T., Kovesdi, I., Benet-Buchholz, J., Dorman, G., Urge, L., and Darvas, F., Tetrahedron, 2003, vol. 59, p.655.

    Article  CAS  Google Scholar 

  20. Borodina, E.A., Orlova, N.A., Gatilov, Yu.V., and Sal’nikova, O.I., Russ. J. Org. Chem., 2015, vol. 51, p. 1745.

    Article  CAS  Google Scholar 

  21. Potkin, V.I., Petkevich, S.K., Kletskov, A.V., Kolesnik, I.A., Zvereva, T.D., Zhukovskaya, N.A., Levkovskaya, G.G., and Rozentsveig, I.B., Russ. J. Org. Chem., 2017, vol. 53, p.240.

    Article  CAS  Google Scholar 

  22. Zou, Y., Zhang, Q., Showkot Hossain, A.M., Sheng-Li Li, Jie-Ying Wu, Wei-Zai Ke, Bao-Kang Jin, Jia-Xiang Yang, Sheng-Yi Zhang, and Yu-Peng Tian, J. Organomet. Chem., 2012, vol. 720, p. 66.

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Institute of Physical Organic Chemistry, National Academy of Sciences of Belarus, ul. Surganova 13, Minsk, 220072, Belarus

    V. I. Potkin, S. K. Petkevich, A. V. Kletskov, I. A. Kolesnik & E. A. Dikusar

  2. Favorskii Irkutsk Institute of Chemistry, Siberian Branch, Russian Academy of Sciences, ul. Favorskogo 1, Irkutsk, 664033, Russia

    I. B. Rozentsveig & G. G. Levkovskaya

  3. Peoples’ Friendship University of Russia, ul. Miklukho-Maklaya 6, Moscow, 117198, Russia

    D. K. Nasirova, K. K. Borisova & F. I. Zubkov

Authors
  1. V. I. Potkin
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. S. K. Petkevich
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. A. V. Kletskov
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. I. A. Kolesnik
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. E. A. Dikusar
    View author publications

    You can also search for this author in PubMed Google Scholar

  6. I. B. Rozentsveig
    View author publications

    You can also search for this author in PubMed Google Scholar

  7. G. G. Levkovskaya
    View author publications

    You can also search for this author in PubMed Google Scholar

  8. D. K. Nasirova
    View author publications

    You can also search for this author in PubMed Google Scholar

  9. K. K. Borisova
    View author publications

    You can also search for this author in PubMed Google Scholar

  10. F. I. Zubkov
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to V. I. Potkin.

Additional information

Original Russian Text © V.I. Potkin, S.K. Petkevich, A.V. Kletskov, I.A. Kolesnik, E.A. Dikusar, I.B. Rozentsveig, G.G. Levkovskaya, D.K. Nasirova, K.K. Borisova, F.I. Zubkov, 2018, published in Zhurnal Organicheskoi Khimii, 2018, Vol. 54, No. 3, pp. 447–456.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Potkin, V.I., Petkevich, S.K., Kletskov, A.V. et al. Synthesis of Azaheterocyclic Cymantrene Derivatives. Russ J Org Chem 54, 452–462 (2018). https://doi.org/10.1134/S1070428018030132

Download citation

  • Received:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1134/S1070428018030132

Search

Navigation