Skip to main content
SpringerLink
Log in

Synthesis of Tetrazole and 1,2,4-Oxadiazole Derivatives of Maleopimaric Acid Methyl Ester

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

Abstract

New tetrazole derivatives were synthesized by 1,3-dipolar cycloaddition of azide ion to N-(2-cyano­ethyl) and N-(2-cyanoethoxy) imides obtained from maleopimaric acid methyl ester. Amidoximation of the same nitriles gave the corresponding amidoximes, and treatment of the latter with acetyl chloride gave analogous 1,2,4-oxadiazole derivatives.

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

Scheme
Scheme

Similar content being viewed by others

REFERENCES

  1. Tolstikov, G.A., Tolstikova, T.G., Shul’ts, E.E., Tolsti­kov, S.E., and Khvostov, M.V., Smolyanye kisloty khvoinykh Rossii. Khimiya, farmakologiya (Rosin Acids from Coniferous Plants of Russia. Chemistry and Pharmacology), Novosibirsk: GEO, 2011.

  2. Khabibullina, G.R., Fedotova, E.S., Tretyakova, E.V., Tyumkina, T.V., Parfenova, L.V., and Ibragimov, A.G., Russ. J. Gen. Chem., 2019, vol. 89, p. 25. https://doi.org/10.1134/S1070363219010055

    Article  CAS  Google Scholar 

  3. Rakhimova, E.B., Kirsanov, V.Yu., Tret’yakova, E.V., Khalilov, L.M., Ibragimov, A.G., Dzhemileva, L.U., D’yakonov, V.A., and Dzhemilev, U.M., RSC Adv., 2020, vol. 10, p. 21039. https://doi.org/10.1039/d0ra03209c

    Article  CAS  Google Scholar 

  4. Tret’yakova, E.V., Salimova, E.V., and Parfenova, L.V., Russ. J. Bioorg. Chem., 2018, vol. 44, p. 547. https://doi.org/10.1134/S1068162018050175

    Article  Google Scholar 

  5. Schuller, W.H., Minor, J.C., Block, S.S., and Lawrence, R.V., US Patent no. 3636215A, 1972.

  6. Wang, J., Chen, Y.P., Yao, K., Wilbon, P.A., Zhang, W., Ren, L., Zhou, J., Nagarkatti, M., Wang, Ch., Chu, F., He, X., Decho, A.W., and Tang, Ch., Chem. Commun., 2012, vol. 48, p. 916. https://doi.org/10.1039/C1CC16432E

    Article  CAS  Google Scholar 

  7. Yao, G.-Y., Ye, M.-Y., Huang, R.-Zh., Li, Y.-J., Zhu, Y.-T., Pan, Y.-M., Liao, Zh.-X., and Wang, H.-Sh., Bioorg. Med. Chem. Lett., 2013, vol. 23, p. 6755. https://doi.org/10.1016/j.bmcl.2013.10.028

    Article  CAS  PubMed  Google Scholar 

  8. Tretyakova, E.V., Smirnova, I.E., Salimova, E.V., and Odinokov, V.N., Bioorg. Med. Chem., 2015, vol. 23, p. 6543. https://doi.org/10.1016/j.bmc.2015.09.006

    Article  CAS  PubMed  Google Scholar 

  9. Tret’yakova, E.V., Salimova, E.V., Shakurova, E.R., Parfenova, L.V., and Odinokov, V.N., Russ. J. Org. Chem., 2017, vol. 53, p. 1701. https://doi.org/10.1134/S1070428017110161

    Article  Google Scholar 

  10. Tretyakova, E.V., Salimova, E.V., and Parfenova, L.V., Nat. Prod. Res., 2020, article ID 1762187. https://doi.org/10.1080/14786419.2020.1762187

  11. Malik, M.A., Wani, M.Y., Al-Thabaiti, Sh.A., and Shiekh, R.A., J. Inclusion Phenom. Macrocyclic Chem., 2014, vol. 78, p. 15. https://doi.org/10.1007/s10847-013-0334-x

    Article  CAS  Google Scholar 

  12. Baykov, S., Semenov, A., Tarasenko, M., and Boyar­skiy, V.P., Tetrahedron Lett., 2020, vol. 61, article ID 152403. https://doi.org/10.1016/j.tetlet.2020.152403

Download references

Funding

This study was performed in the framework of state assignment no. AAAA-A20-120012090023-8.

Author information

Authors and Affiliations

  1. Ufa Institute of Chemistry, Ufa Federal Research Center, Russian Academy of Sciences, 450054, Ufa, Russia

    E. V. Tret’yakova

Authors
  1. E. V. Tret’yakova
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to E. V. Tret’yakova.

Ethics declarations

The author declares the absence of conflict of interest.

Additional information

Translated from Zhurnal Organicheskoi Khimii, 2021, Vol. 57, No. 3, pp. 420–425 https://doi.org/10.31857/S0514749221030101.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Tret’yakova, E.V. Synthesis of Tetrazole and 1,2,4-Oxadiazole Derivatives of Maleopimaric Acid Methyl Ester. Russ J Org Chem 57, 391–395 (2021). https://doi.org/10.1134/S1070428021030106

Download citation

  • Received:

  • Revised:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1134/S1070428021030106

Keywords:

Search

Navigation