SpringerLink
Log in

Synthesis of 2-(Tetrazolylacetyl)cyclohexane-1,3-diones

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

Abstract

2-(Tetrazolylacetyl)cyclohexane-1,3-diones were synthesized via C-acylation of cyclohexane-1,3-diones with tetrazolylacetic acids in the presence of 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride and N,N-dimethylaminopyridine in acetonitrile at room temperature. Structure of the synthesized compounds was confirmed by 1H, 13C NMR spectroscopy, as well as two-dimensional NMR spectroscopy methods.

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

Access this article

Log in via an institution

Subscribe and save

Springer+ Basic
EUR 32.99 /Month
  • Get 10 units per month
  • Download Article/Chapter or Ebook
  • 1 Unit = 1 Article or 1 Chapter
  • Cancel anytime
Subscribe now

Buy Now

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

Instant access to the full article PDF.

Institutional subscriptions

Scheme
Scheme

Similar content being viewed by others

REFERENCES

  1. Ray, L. and Moore, B.S., Nat. Prod. Rep., 2016, vol. 33, no. 2, p. 150. https://doi.org/10.1039/c5np00112a

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  2. Polyketides: Biosynthesis, Biological Activity, and Genetic Engineering, Rimando, A.M. and Baerson, S.R., Eds., Oxford: University Press, 2007. 296 p.

  3. Rubinov, D.B., Rubinova, I.L., and Akhrem, A.A., Chem. Nat. Compd., 1995, vol. 31, no. 5, p. 537. https://doi.org/10.1007/BF01164877

    Article  Google Scholar 

  4. Lakhvich, F.A. and Khlebnicova, T.S., Izv. Akad Nauk Belarusi, Ser. Khim. Nauk, 1996, no. 4, p. 101.

    Google Scholar 

  5. Gatadi, S., Gour, J., and Nanduri, S., Bioorg. Med. Chem., 2019, vol. 27, no. 17, p. 3760. https://doi.org/10.1016/j.bmc.2019.07.023

    Article  CAS  PubMed  Google Scholar 

  6. Bocquet, L., Sahpaz, S., Hilbert, J.L., Rambaud, C., and Riviere, C., Phytochem. Rev., 2018, vol. 17, no. 5, p. 1047. https://doi.org/10.1007/s11101-018-9584-y

    Article  CAS  Google Scholar 

  7. Santucci, A., Bernardini, G., Braconi, D., Petricci, E., and Manetti, F., J. Med. Chem., 2017, vol. 60, no. 10, p. 4101. https://doi.org/10.1021/acs.jmedchem.6b01395

    Article  CAS  PubMed  Google Scholar 

  8. Reber, K.P. and Burdge, H., Org. Prep. Proc. Int., 2018, vol. 50, no. 1, p. 2. https://doi.org/10.1080/00304948.2018.1405332

    Article  CAS  Google Scholar 

  9. Lakhvich, F.A., Khlebnicova, T.S., and Akhrem, A.A., Synthesis, 1985, no. 8, p. 784. https://doi.org/10.1055/s-1985-31348

    Article  Google Scholar 

  10. Schmidt, A. and Boland, W., J. Org. Chem., 2007, vol. 72, no. 5, p. 1699. https://doi.org/10.1021/jo062359x

    Article  CAS  PubMed  Google Scholar 

  11. Beaudegnies, R., Edmunds, A.J.F., Fraser, T.E.M., Hall, R.G., Hawkes, T.R., Mitchell, G., Schaetzer, J., Wendeborn, S., and Wibley, J., Bioorg. Med. Chem., 2009, vol. 17, no. 12, p. 4134. https://doi.org/10.1016/j.bmc.2009.03.015

    Article  CAS  PubMed  Google Scholar 

  12. Popova, E.A., Trifonov, R.E., and Ostrovskii, V.A., Russ. Chem. Rev., 2019, vol. 88, no. 6, p. 644. https://doi.org/10.1070/RCR4864

    Article  CAS  Google Scholar 

  13. Myznikov, L.V., Hrabalek, A., and Koldobskii, G.I., Chem. Heterocycl. Compd., 2007, vol. 43, no. 1, p. 1. https://doi.org/10.1007/s10593-007-0001-5

    Article  CAS  Google Scholar 

  14. Akhrem, A.A., Lakhvich, F.A., Budai, S.I., Khlebnicova, T.S., and Petrusevich, I.I., Synthesis, 1978, no. 12, p. 925. https://doi.org/10.1055/s-1978-24943

    Article  Google Scholar 

  15. Lakhvich, F.A., Kozinets, V.A., and Khlebnicova, T.S., Zh. Org. Khim., 1992, vol. 28, no. 6, p. 1634.

    CAS  Google Scholar 

  16. Montes, I.F. and Burger, U., Tetrahedron Lett., 1996, vol. 37, no. 7, p. 1007. https://doi.org/10.1016/0040-4039(95)02362-3

    Article  CAS  Google Scholar 

  17. Oliver, J.E., Wilzer, K.R., and Waters, R.M., Synthesis, 1990, no. 12, p. 1117. https://doi.org/10.1055/s-1990-27107

    Article  Google Scholar 

  18. Tabuchi, H., Hamamoto, T., and Ichihara, A., Synlett., 1993, no. 9, p. 651. https://doi.org/10.1055/s-1993-22558

    Article  Google Scholar 

  19. Kohout, M., Bielec, B., Steindl, P., Trettenhahn, G., and Lindner, W., Tetrahedron, 2015, vol. 71, no. 18, p. 2698. https://doi.org/10.1016/j.tet.2015.03.037

    Article  CAS  Google Scholar 

  20. Gundoju, N.R., Bokam, R., Yalavarthi, N.R., Buddana, S.K., Prakasham, R.S., and Ponnapalli, M.G., J. Asian Nat. Prod. Res., 2019, vol. 21, no. 3, p. 262. https://doi.org/10.1080/10286020.2018.1460362

    Article  CAS  PubMed  Google Scholar 

  21. Khlebnicova, T.S., Isakova, V.G., Baranovsky, A.V., Borisov, E.V., and Lakhvich, F.A., J. Fluorine Chem., 2006, vol. 127, no. 12, p. 1564. https://doi.org/10.1016/j.jfluchem.2006.08.003

    Article  CAS  Google Scholar 

  22. Forsen, S., Merenyi, F., and Nilsson, M., Acta Chem. Scand., 1964, vol. 18, no. 5, p. 1208.

    Article  CAS  Google Scholar 

  23. Kuzmina, N.E., Moiseev, S.V., and Luttseva, A.I., Pharm. Chem. J., 2021, vol. 55, no. 4, p. 396. https://doi.org/10.1007/s11094-021-02434-9

    Article  CAS  Google Scholar 

  24. Khlebnikova, T.S., Isakova, V.G., Baranovskii, A.V., Lakhvich, F.A., and Lyakhov, A.S., Russ. J. Gen. Chem., 2007, vol. 77, no. 10, p. 1724. https://doi.org/10.1134/S1070363207100118

    Article  CAS  Google Scholar 

  25. Kamiya, T. and Saito Yo., US Patent 3767667, 1973.

  26. Nohara, A., Kato, T., Kawarazaki, T., and Sawa, Yo., GB Patent 1549094, 1979.

  27. Becker, H.G.O., Beckert, R., Berger, W., Gewald, K., Gentz, F., Gluch, R., Domshke, G., Seiler, E., Mayer, R., Metz, P., Müller, K., Pavel, D., Fanghänel, E., Faust, J., Fisher, M., Habicher, W., Schwetlick, K., Schmidt, H., Schollberg, K., and Zeppenfeld, G., Organikum, Weinheim: Wiley-VHC, 2009.

  28. Raap, R. and Howard, J., Can. J. Chem., 1969, vol. 47, no. 5, p. 813.

    Article  CAS  Google Scholar 

Download references

Funding

This work was financially supported by the Belarusian Republican Foundation for Basic Research (project X20P-226) and the Russian Foundation for Basic Research (project 20-53-00039-Bel_a).

Author information

Authors and Affiliations

  1. Institute of Bioorganic Chemistry, National Academy of Sciences of Belarus, 220141, Minsk, Belarus

    T. S. Khlebnicova, V. G. Zinovich, Yu. A. Piven, A. V. Baranovsky & F. A. Lakhvich

  2. St. Petersburg State Institute of Technology, 190013, St. Petersburg, Russia

    R. E. Trifonov

Authors
  1. T. S. Khlebnicova
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. V. G. Zinovich
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Yu. A. Piven
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. A. V. Baranovsky
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. F. A. Lakhvich
    View author publications

    You can also search for this author in PubMed Google Scholar

  6. R. E. Trifonov
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to T. S. Khlebnicova.

Ethics declarations

No conflict of interest was declared by the authors.

Additional information

Translated from Zhurnal Obshchei Khimii, 2021, Vol. 91, No. 8, pp. 1159–1165 https://doi.org/10.31857/S0044460X21080023.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Khlebnicova, T.S., Zinovich, V.G., Piven, Y.A. et al. Synthesis of 2-(Tetrazolylacetyl)cyclohexane-1,3-diones. Russ J Gen Chem 91, 1438–1443 (2021). https://doi.org/10.1134/S1070363221080028

Download citation

  • Received:

  • Revised:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1134/S1070363221080028

Keywords:

Search

Navigation