Russian Journal of Organic Chemistry

, Volume 54, Issue 8, pp 1250–1255 | Cite as

One-Pot Synthesis of 3,5-Disubstituted 1,2,4-Oxadiazoles Using Catalytic System NaOH‒DMSO

  • V. E. Pankrat’eva
  • T. V. Sharonova
  • M. V. TarasenkoEmail author
  • S. V. Baikov
  • E. R. Kofanov


One-pot convenient process was developed for the production of 3,5-disubstituted 1,2,4-oxadiazoles by reaction of amidoximes with anhydrides or acyl chlorides in a system NaOH‒DMSO. The reaction proceeds at room temperature with high yields.


Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.


  1. 1.
    Boström, J., Hogner, A., Llinàs, A., Wellner, E., and Plowright, A., J. Med. Chem., 2012, vol. 55, p. 1817.CrossRefPubMedGoogle Scholar
  2. 2.
    Vaidya, A., Jain, S., Jain, P., Jain, P., Tiwari, N., Jain, R., Jain, R., Jain, A.K., and Agrawal, R.K., Mini-Rev. Med. Chem., 2016, vol. 16, p.825.CrossRefPubMedGoogle Scholar
  3. 3.
    Khan, I., Ibrar, A., and Abbas, N., Arch. Pharm., 2013, vol. 347, p.1.CrossRefGoogle Scholar
  4. 4.
    Spink, E., Ding, D., Peng, Z., Boudreau, M., Leemans, E., Lastochkin, E., Song, W., Lichtenwalter, K., O’Daniel, P., Testero, S., Pi, H., Schroeder, V., Wolter, W., Antunes, N., Suckow, M., Vakulenko, S., Chang, M., and Mobashery, S., J. Med. Chem., 2015, vol. 58, p. 1380.CrossRefPubMedGoogle Scholar
  5. 5.
    Karad, S., Purohit, V., Thummar, R., Vaghasiya, B., Kamani, R., Thakor, P., Thakkar, V., Thakkar, S., Ray, A., and Raval, D., Eur. J. Med. Chem., 2017, vol. 126, p.894.CrossRefPubMedGoogle Scholar
  6. 6.
    Gold, B., Smith, R., Nguyen, Q., Roberts, J., Ling, Y., Lopez Quezada, L., Somersan, S., Warrier, T., Little, D., Pingle, M., Zhang, D., Ballinger, E., Zimmerman, M., Dartois, V., Hanson, P., Mitscher, L., Porubsky, P., Rogers, S., Schoenen, F., Nathan, C., and Aubé, J., J. Med. Chem., 2016, vol. 59, p. 6027.CrossRefPubMedPubMedCentralGoogle Scholar
  7. 7.
    Rubino, S., Pibiri, I., Costantino, C., Buscemi, S., Girasolo, M., Attanzio, A., and Tesoriere, L., J. Inorg. Biochem., 2016, vol. 155, p.92.CrossRefPubMedGoogle Scholar
  8. 8.
    Jiang, C., Fu, Y., Zhang, L., Gong, J., Wang, Z., Xiao, W., Zhang, H., and Guo, Y., Bioorg. Med. Chem. Lett., 2015, vol. 25, p.216.CrossRefPubMedGoogle Scholar
  9. 9.
    Gilmore, J., Sheppeck, J., Watterson, S., Haque, L., Mukhopadhyay, P., Tebben, A., Galella, M., Shen, D., Yarde, M., Cvijic, M., Borowski, V., Gillooly, K., Taylor, T., McIntyre, K., Warrack, B., Levesque, P., Li, J., Cornelius, G., D’Arienzo, C., Marino, A., Balimane, P., Salter-Cid, L., Barrish, J., Pitts, W., Carter, P., Xie, J., and Dyckman, A., J. Med. Chem., 2016, vol. 59, p. 6248.CrossRefPubMedGoogle Scholar
  10. 10.
    Bokor, É., Szennyes, E., Csupász, T., Tóth, N., Docsa, T., Gergely, P., and Somsák, L., Carbohydr. Res., 2015, vol. 412, p.71.CrossRefPubMedGoogle Scholar
  11. 11.
    Krasavin, M., Shetnev, A., Sharonova, T., Baykov, S., Tuccinardi, T., Kalinin, S., Angeli, A., and Supuran, C.T., Bioorg. Chem., 2018, vol. 76, p.88.CrossRefPubMedGoogle Scholar
  12. 12.
    Csürös, L., Ther. Hung., 1989, vol. 37, p.50.PubMedGoogle Scholar
  13. 13.
    Palazzo, G., Tavella, M., Strani, G., and Silvestrini, B., J. Med. Chem., 1961, vol. 4, p.351.CrossRefGoogle Scholar
  14. 14.
    Peltz, S., Morsy, M., Welch, E., and Jacobson, A., Annu. Rev. Med., 2013, vol. 64, p.407.CrossRefPubMedGoogle Scholar
  15. 15.
    Pace, A., Buscemi, S., Piccionello, A., and Pibiri, I., Adv. Heterocycl. Chem., 2015, p.85.Google Scholar
  16. 16.
    Matta, A., Bahadur, V., Taniike, T., Van der Eycken, J., and Singh, B., Dyes Pigm., 2017, vol. 140, p.250.CrossRefGoogle Scholar
  17. 17.
    Yu, Q., Cheng, G., Ju, X., Lu, C., Lin, Q., and Yang, H., New J. Chem., 2017, vol. 41, p. 1202.CrossRefGoogle Scholar
  18. 18.
    Pace, A. and Pierro, P., Org. Biomol. Chem., 2009, vol. 7, p. 4337.CrossRefPubMedGoogle Scholar
  19. 19.
    Augustine, J., Akabote, V., Hegde, S., and Alagarsamy, P., J. Org. Chem., 2009, vol. 74, p. 5640.CrossRefPubMedGoogle Scholar
  20. 20.
    NevesFilho, R., da Silva-Alves, D., dos Anjos, J., and Srivastava, R., Synth. Commun., 2013, vol. 43, p. 2596.CrossRefGoogle Scholar
  21. 21.
    Agat’ev, P., Shlenev, R., Tarasov, A., and Danilova, A., Russ. J. Org. Chem., 2015, vol. 51, p. 988. doi 10.1134/S1070428015070167CrossRefGoogle Scholar
  22. 22.
    Sangepu, B., Gandu, B., Anupoju, G., and Jetti, V., J. Heterocycl. Chem., 2015, vol. 53, p.754.CrossRefGoogle Scholar
  23. 23.
    Kuram, M.R., Kim, W.G., Myung, K., and Hong, S.Y., Eur. J. Org. Chem., 2016, vol. 3, p.438.CrossRefGoogle Scholar
  24. 24.
    Pierce, J. and Parker, P., Synthesis, 2016, vol. 48, p. 1902.CrossRefGoogle Scholar
  25. 25.
    Baykov, S., Sharonova, T., Osipyan, A., Rozhkov, S., Shetnev, A., and Smirnov, A., Tetrahedron Lett., 2016, vol. 57, p. 2898.CrossRefGoogle Scholar
  26. 26.
    Baykov, S., Sharonova, T., Shetnev, A., Rozhkov, S., Kalinin, S., and Smirnov, A., Tetrahedron, 2017, vol. 73, p.945.CrossRefGoogle Scholar
  27. 27.
    Sharonova, T., Pankrat’eva, V., Savko, P., Baykov, S., and Shetnev, A., Tetrahedron Lett., 2018, vol. 59, p. 2824.CrossRefGoogle Scholar
  28. 28.
    Tarasenko, M., Duderin, N., Sharonova, T., Baykov, S., Shetnev, A., and Smirnov, A.V., Tetrahedron Lett., 2017, vol. 58, p. 3672.CrossRefGoogle Scholar
  29. 29.
    Tsiulin, P., Sosnina, V., Krasovskaya, G., Danilova, A., Baikov, S., and Kofanov, E., Russ. J. Org. Chem., 2011, vol. 47, p. 1874. doi 10.1134/S1070428011120153CrossRefGoogle Scholar
  30. 30.
    Christopher, A.R., Scriven, E.F.V., Taylor, R.J.K., Comprehensive Heterocyclic Chemistry III, Katritzky, A.R., Ed., Elsevier Ltd, 2008, vol. 5, p.258.Google Scholar
  31. 31.
    Johnson, J., Nwoko, D., Hotema, M., Sanchez, N., Alderman, R., and Lynch, V., J. Heterocycl. Chem., 1996, vol. 33, p. 1583.CrossRefGoogle Scholar
  32. 32.
    Kivrak, A. and Zora, M., Tetrahedron, 2014, vol. 70, p.817.CrossRefGoogle Scholar
  33. 33.
    Bedford, C.D., Howd, R.A., Dailey, O.D., Miller, A., Nolen, H.W. III, Kenley, R.A., Kern, J.R., and Winterle, J.S., J. Med. Chem., 1986, vol. 29, p. 2174.CrossRefPubMedGoogle Scholar

Copyright information

© Pleiades Publishing, Ltd. 2018

Authors and Affiliations

  • V. E. Pankrat’eva
    • 1
  • T. V. Sharonova
    • 1
  • M. V. Tarasenko
    • 2
    Email author
  • S. V. Baikov
    • 3
  • E. R. Kofanov
    • 2
  1. 1.Transfer Center of Pharmaceutical TechnologyUshinski Yaroslavl State Pedagogical UniversityYaroslavlRussia
  2. 2.Yaroslavl State Technical UniversityYaroslavlRussia
  3. 3.St. Petersburg State UniversitySt. PetersburgRussia

Personalised recommendations