Skip to main content
Log in

Synthesis of 5-oxo-1-(5-R-1,3,4-thiadiazol-2-yl)pyrrolidine-3-carboxylic acids

  • Full Articles
  • Published:
Russian Chemical Bulletin Aims and scope

Abstract

A series of new heterocyclic ensembles, derivatives of 5-oxo-1-(1,3,4-thiadiazol-2-yl)-pyrrolidine-3-carboxylic acid, was synthesized by heating 5-substituted 1,3,4-thiadiazol-2-amines and itaconic acid under solvent-free conditions or with the addition of acetic acid at 140–150 °C. The resulting acids can be used as building blocks in the synthesis of new potentially biologically active heterocyclic compounds.

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

Access this article

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

Instant access to the full article PDF.

References

  1. K. L. Obydennov, T. V. Glukhareva, Chem. Heterocycl. Compd., 2019, 55, 1013; DOI: https://doi.org/10.1007/s10593-019-02571-w.

    Article  Google Scholar 

  2. K. A. Kochetkov, O. N. Gorunova, N. A. Bystrova, P. V. Dudina, M. G. Akimov, Russ. Chem. Bull., 2022, 71, 2395; DOI: https://doi.org/10.1007/s11172-022-3667-z.

    Article  CAS  Google Scholar 

  3. A. A. Larin, A. V. Shaferov, K. A. Monogarov, D. B. Meerov, A. N. Pivkina, L. L. Fershtat, Mendeleev Commun., 2022, 32, 111; DOI: https://doi.org/10.1016/j.mencom.2022.01.036.

    Article  CAS  Google Scholar 

  4. O. A. Vysokova, T. A. Kalinina, M. A. Tokareva, T. A. Pospelova, T. V. Glukhareva, Yu. Yu. Morzherin, Chem. Heterocycl. Compd., 2017, 53, 236; DOI: https://doi.org/10.1007/s10593-017-2045-5.

    Article  CAS  Google Scholar 

  5. T. A. Kalinina, L. A. Khamidullina, Yu. S. Shakhmina, T. V. Glukhareva, A. A. Kochubei, O. E. Cherepanova, Z. Fan, Y. Zhu, Yu. Yu. Morzherin, Chem. Heterocycl. Compd., 2016, 52, 910; DOI: https://doi.org/10.1007/s10593-017-1986-z.

    Article  CAS  Google Scholar 

  6. A. M. Starosotnikov, M. A. Bastrakov, V. A. Kokorekin, Russ. Chem. Bull., 2022, 71, 474; DOI: https://doi.org/10.1007/s11172-022-3435-0.

    Article  CAS  Google Scholar 

  7. A. N. Aksenov, M. M. Krayushkin, V. N. Yarovenko, Russ. Chem. Bull., 2021, 70, 1131; DOI: https://doi.org/10.1007/s11172-021-3194-3.

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  8. Y. Hu, C.-Y. Li, X.-M. Wang, Y.-H. Yang, H.-L. Zhu, Chem. Rev., 2014, 114, 5572; DOI: https://doi.org/10.1021/cr400131u.

    Article  CAS  PubMed  Google Scholar 

  9. L. I. Belen’kii, G. A. Gazieva, Y. B. Evdokimenkova, N. O. Soboleva, Adv. Heterocycl. Chem., 2022, 136, 225; DOI: https://doi.org/10.1016/bs.aihch.2021.09.002.

    Article  Google Scholar 

  10. V. L. Rusinov, I. M. Sapozhnikova, A. A. Spasov, O. N. Chupakhin, Russ. Chem. Bull., 2022, 71, 2561; DOI: https://doi.org/10.1007/s11172-022-3687-8.

    Article  CAS  Google Scholar 

  11. G. A. Selivanova, E. V. Tretyakov, Russ. Chem. Bull., 2020, 69, 838; DOI: https://doi.org/10.1007/s11172-020-2842-3.

    Article  CAS  Google Scholar 

  12. Q. H. Zhang, L. L. Fershtat, Energetic Materials Frontiers, 2022, 3, 109; DOI: https://doi.org/10.1016/j.enmf.2022.09.002.

    Article  Google Scholar 

  13. S. Janowska, A. Paneth, M. Wujec, Molecules, 2020, 25, 4309; DOI: https://doi.org/10.3390/molecules25184309.

    Article  PubMed  PubMed Central  Google Scholar 

  14. J. Dong, Q. Pei, P. Wang, Q. Ma, W. Hu, Arabian J. Chem., 2022, 15, 103712; DOI: https://doi.org/10.1016/j.arabjc.2022.103712.

    Article  CAS  Google Scholar 

  15. M. Gür, S. Yerlikaya, N. Sener, S. Özkınalı, M. C. Baloglu, H. Gokçe, Y. C. Altunoglu, S. Demir, I. Sener, J. Mol. Struct., 2020, 1219, 128570; DOI: https://doi.org/10.1016/j.molstruc.2020.128570.

    Article  Google Scholar 

  16. Q. Wu, H. Cai, T. Yuan, S. Li, X. Gan, B. Song, Bioorg. Med. Chem. Lett., 2020, 30, 127113; DOI: https://doi.org/10.1016/j.bmcl.2020.127113.

    Article  CAS  PubMed  Google Scholar 

  17. S. A. Serkov, N. V. Sigai, N. N. Kostikova, P. V. Bulatov, M. A. Epishina, Pharm. Chem. J., 2014, 48, 20; DOI: https://doi.org/10.1007/s11094-014-1037-3.

    Article  CAS  Google Scholar 

  18. G. Sravya, G. Yamini, V. Padmavathi, A. Padmaja, Eur. J. Med. Chem., 2016, 122, 647; DOI: https://doi.org/10.1016/j.ejmech.2016.06.014.

    Article  CAS  PubMed  Google Scholar 

  19. V. L. Gein, T. A. Silina, A. A. Cherepanov, A. P. Shishkin, I. P. Bulatov, N. V. Dozmorova, R. R. Makhmudov, Pharm. Chem. J., 2021, 55, 23; DOI: https://doi.org/10.1007/s11094-021-02366-4.

    Article  CAS  Google Scholar 

  20. K. Kairytė, B. Grybaitė, R. Vaickelionienė, B. Sapijanskaitė-Banevič, P. Kavaliauskas, V. Mickevičius, Pharmaceuticals, 2022, 15, 970; DOI: https://doi.org/10.3390/ph15080970.

    Article  PubMed  PubMed Central  Google Scholar 

  21. Pat. WO2006014944A1; https://patents.google.com/patent/WO2006014944A1/en.

  22. Pat. RU2017135273A; https://patents.google.com/patent/RU2017135273A/ru.

  23. Pat. WO2020175134A1; https://patents.google.com/patent/WO2020175134A1/en.

  24. G. S. Kumar, Y. Poornachandra, K. R. Reddy, C. G. Kumar, B. Narsaiah, Synthetic Commun., 2017, 47, 1864; DOI: https://doi.org/10.1080/00397911.2017.1354379.

    Article  CAS  Google Scholar 

  25. L. Amarouche, F. T. Brahimi, A. A. Othman, J. Chem. Pharm. Res., 2016, 8, 896.

    CAS  Google Scholar 

  26. A. Voskienė, B. Sapijanskaitė, V. Mickevičius, I. Jonuš-kienė, M. Stasevych, O. Komarovska-Porokhnyavets, R. Musyanovych, V. Novikov, Molecules, 2012, 17, 14434; DOI: https://doi.org/10.3390/molecules171214434.

    Article  PubMed  PubMed Central  Google Scholar 

  27. P. L. Paytash, E. Sparrow, J. C. Gathe, J. Am. Chem. Soc., 1950, 72, 1415; DOI: https://doi.org/10.1021/ja01159a520.

    Article  CAS  Google Scholar 

  28. V. L. Gein, T. A. Silina, A. A. Cherepanov, A. P. Shishkin, B. Ya. Syropyatov, E. V. Voronina, L. I. Varkentin, Russ. J. Gen. Chem., 2016, 86, 2693; DOI: https://doi.org/10.1134/S1070363216120203.

    Article  CAS  Google Scholar 

  29. Yu. V. Kharchenko, O. S. Detistov, V. D. Orlov, Chem. Heterocycl. Compd., 2008, 44, 600; DOI: https://doi.org/10.1007/s10593-008-0080-y.

    Article  CAS  Google Scholar 

  30. Y. Han, Y. Sun, A. Abdukader, B. Liu, D. Wang, Catalysis Lett., 2018, 148, 3486; DOI: https://doi.org/10.1007/s10562-018-2541-y.

    Article  CAS  Google Scholar 

  31. S. A. Serkov, N. V. Sigai, N. N. Kostikova, A. E. Fedorov, G. A. Gazieva, Russ. Chem. Bull., 2022, 71, 1801; DOI: https://doi.org/10.1007/s11172-022-3592-1.

    Article  CAS  Google Scholar 

  32. S. A. Serkov, N. V. Sigay, N. N. Kostikova, A. E. Fedorov, A. P. Tyurin, G. A. Gazieva, Chem. Heterocycl. Compd., 2022, 58, 514; DOI: https://doi.org/10.1007/s10593-022-03121-7.

    Article  CAS  Google Scholar 

  33. Clinical and Laboratory Standards Institute (CLSI) Performance Standards for Antimicrobial Susceptibility Testing: Twenty Fifth Informational Supplement, CLSI Document M100–S25, CLSI, Wayne, PA, 2015.

  34. CLSI Methods for Dilution Antimicrobial Susceptibility Tests for Bacteria that Grow Aerobically; Approved Standard, 10th ed., CLSI document M07–A10, CLSI, Wayne, PA, 2015.

  35. CLSI Reference Method for Broth Dilution Antifungal Susceptibility Testing of Yeasts; Approved Standard, 3rd ed., CLSI document M27–A3, CLSI, Wayne, PA, 2008.

Download references

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to G. A. Gazieva.

Ethics declarations

The authors declare no competing interests.

Additional information

No human or animal subjects were used in this research.

Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, Vol. 72, No. 8, pp. 1837–1843, August, 2023.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Serkov, S.A., Sigay, N.V., Kostikova, N.N. et al. Synthesis of 5-oxo-1-(5-R-1,3,4-thiadiazol-2-yl)pyrrolidine-3-carboxylic acids. Russ Chem Bull 72, 1837–1843 (2023). https://doi.org/10.1007/s11172-023-3966-z

Download citation

  • Received:

  • Revised:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11172-023-3966-z

Key words

Navigation