Skip to main content
Log in

A convenient route to the 1,2,5-oxadiazole-substituted 1,2,4-triazolo[1,5-a]pyrimidine derivatives

  • Published:
Chemistry of Heterocyclic Compounds Aims and scope

A convenient synthesis of 1,2,4-triazole and 1,2,4-triazolo[1,5-a]pyrimidines with 3-amino-1,2,5-oxadiazole substituent starting from available 4-amino-1,2,5-oxadiazole-3-carbohydrazide and benzoyl cyanamide has been developed.

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.

Similar content being viewed by others

References

  1. Ananikov, V. P.; Khokhlova, E. A.; Egorov, M. P.; Sakharov, A. M.; Zlotin, S. G.; Kucherov, A. V.; Kustov, L. M.; Gening, M. L.; Nifantiev, N. E. Mendeleev Commun. 2015, 25, 75.

    Article  CAS  Google Scholar 

  2. Design of Hybrid Molecules for Drug Development; Decker, M., Ed.; Elsevier: Würzburg, 2017.

  3. Shaikh, M. S.; Palkar, M. B.; Patel, H. M.; Rane, R. A.; Alwan, W. S.; Shaikh, M. M.; Shaikh, I. M.; Hampannavar, G. A.; Karpoormath, R. RSC Adv. 2014, 4, 62308.

    Article  CAS  Google Scholar 

  4. Decker, M. Curr. Med. Chem. 2011, 18, 1464.

    Article  CAS  Google Scholar 

  5. Tsogoeva, S. B. Mini–Rev. Med. Chem. 2010, 10, 773.

    Article  CAS  Google Scholar 

  6. Glanville, A. R.; Scot, A. I.; Morton, J. M.; Aboyoun, C. L.; Plit, M. L.; Carter, I. W.; Malouf, M. A. J. Heart Lung Transplant. 2005, 24, 2114.

    Article  Google Scholar 

  7. Chudinov, M. V.; Matveev, A. V; Prutkov, A. N.; Konstantinova, I. D.; Fateev, I. V.; Prasolov, V. S.; Smirnova, O. A.; Ivanov, G. A.; Galegov, A. V.; Deryabin, P. G. Mendeleev Commun. 2016, 26, 214.

    Article  CAS  Google Scholar 

  8. Cha, R.; Sobel, J. D. Expert Rev. Anti–Infect. Ther. 2004, 2, 357.

    Article  CAS  Google Scholar 

  9. Bel'skaya, N. P.; Demina, M. A.; Sapognikova, S. G.; Fan, Z.-J.; Zhang, H.-K.; Dehaen, W.; Bakulev, V. A. ARKIVOC 2008, (xvi), 9.

  10. Mitchell, G. WO Patent 144234 A1, 2013.

  11. Baumann, K.; Floh, A.; Goetschi, E.; Jacobsen, H.; Jolidon, S.; Luebbers, T. US Patent 20090215759 A1, 2009.

  12. Bell, K.; Sunose, M.; Ellard, K.; Cansfield, A.; Taylor, J.; Miller, W.; Ramsden, N.; Bergamini, G.; Neubauer, G. Bioorg. Med. Chem. Lett. 2012, 22, 5257.

    Article  CAS  Google Scholar 

  13. Gregory, T. F.; Wright, J. L.; Wise, L. D.; Meltzer, L. T.; Serpa, K. A.; Konkoy, C. S.; Whittemore, E. R.; Woodward, R. M. Bioorg. Med. Chem. Lett. 2000, 10, 527.

    Article  CAS  Google Scholar 

  14. Zhao, X.-L.; Zhao, Y.-F.; Guo, S.-C.; Song, H.-S.; Wang, D.; Gong, P. Molecules 2007, 12, 1136.

    Article  CAS  Google Scholar 

  15. Wu, L.; Zhang, C.; Li, W. Bioorg. Med. Chem. Lett. 2013, 23, 5002.

    Article  CAS  Google Scholar 

  16. (a) Girasolo, M. A.; Canfora, L.; Sabatino, P.; Schillaci, E.; Foresti, D.; Rubino, S.; Ruisi, G.; Stocco, G. J. Inorg. Biochem. 2012, 106, 156. (b) Łakomska, I.; Fandzloch, M.; Popławska, B.; Sitkowski, J. Spectrochim. Acta, Part A 2012, 91, 126.

  17. Sheridan, M.; Heal, J. R.; Hamilton, W. D. O.; Pike, I. WO Patent 2012080729 A2, 2012.

  18. Yu, C.; Goddard, W.; Clearfield, E.; Mills, C.; Xiao, T.; Guo, H.; Morrey, J. D.; Motter, N. E.; Zhao, K.; Block, T. M.; Cuconati, A.; Xu, X. J. Med. Chem. 2011, 54, 5660.

    Article  CAS  Google Scholar 

  19. Fershtat, L. L.; Epishina, M. A.; Ovchinnikov, I. V.; Kachala, V. V.; Makhova, N. N. Chem. Hetеrocуcl. Compd. 2015, 51, 754. [Khim. Geterotsikl. Soedin. 2015, 51, 754.]

  20. Paton, R. M. In Comprehensive Heterocyclic Chemistry II; Katritzky, A. R.; Rees, C. W.; Scriven, E. F. V., Eds.; Pergamon: Oxford, 1996, Vol. 4, p. 229.

    Chapter  Google Scholar 

  21. Prezent, M. A.; Daeva, E. D.; Baranin, S. V.; Dorokhov, V. A. Russ. Chem. Bull., Int. Ed. 2015, 64, 1089. [Izv. Akad. Nauk, Ser. Khim. 2015, 1089.]

  22. (a) Prezent, M. A.; Daeva, E. D.; Baranin, S. V.; Zavarzin, I. V. Mendeleev Commun. 2017, 27, 169. (b) Astakhov, A. V.; Suponitsky, K. Yu.; Chernyshev, V. M. Mendeleev Commun. 2018, 28, 439.

  23. Shaposhnikov, S. D.; Korobov, N. V.; Sergievskii, A. V.; Pirogov, S. V.; Mel'nikova, S. F.; Tselinskii, I. V. Russ. J. Org. Chem. 2002, 38, 1351. [Zh. Org. Khim. 2002, 38, 1405.]

  24. Tang, Y.; Imler, G. H.; Parrish, D. A.; Shreeve, J. M. Org. Lett. 2018, 20, 8039.

    Article  CAS  Google Scholar 

  25. Xu, Z.; Cheng, G.; Yang, H.; Zhang, J.; Shreeve, J. M. Chem.–Eur. J. 2018, 24, 10488.

    Article  CAS  Google Scholar 

  26. Saldago, A.; Varela, C.; Garcia Collazo, A. M.; Pevarello, P. Magn. Reson. Chem. 2010, 48, 614.

    Google Scholar 

  27. Crowther, A. F.; Curd, F. H. S.; Rose, F. L. J. Chem. Soc. 1948, 586.

  28. Aleksandrova, N. S.; Semyakin, S. S.; Anisimov, A. A.; Struchkova, M. I.; Sheremetev, A. B. Russ. Chem. Bull., Int. Ed. 2018, 67, 2035. [Izv. Akad. Nauk, Ser. Khim. 2018, 2035.]

Download references

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to Sergey V. Baranin.

Additional information

Supplementary information file, containing 1H and 13C NMR spectra of compounds 10a,b, is available at the journal website http://link.springer.com/journal/10593.

Published in Khimiya Geterotsiklicheskikh Soedinenii, 2019, 55(11), 1131–1134

Electronic supplementary material

ESM 1

(PDF 1035 kb)

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Prezent, M.A., Baranin, S.V. A convenient route to the 1,2,5-oxadiazole-substituted 1,2,4-triazolo[1,5-a]pyrimidine derivatives. Chem Heterocycl Comp 55, 1131–1134 (2019). https://doi.org/10.1007/s10593-019-02590-7

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10593-019-02590-7

Keywords

Navigation