Skip to main content
SpringerLink
Log in

A novel one-pot synthesis method of 3,4,5-triaryl-substituted 1,2,4-triazoles

  • Published:
Chemistry of Heterocyclic Compounds Aims and scope

A novel method for the preparation of 3,4,5-triaryl-substituted 1,2,4-triazoles by the reaction of hydrazides with secondary amides in polyphosphoric ester has been developed. The new method is characterized by mild conditions and ease of synthesis, including the stages of isolation and purification of the product. Additionally, product structures were confirmed by counter synthesis. It was shown that the proposed method is suitable for producing 1,2,4-triazoles with phenolic substituents without the stages of the protection and deprotection of the hydroxyl group. Using the new method, five 3,4,5-substituted 1,2,4-triazoles were obtained for the first time.

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

Similar content being viewed by others

References

  1. Swathi, N. P.; Alva, V. D. P.; Samshuddin, S. J. Bio Tribo-Corros.2017, 3, 42.

    Article  Google Scholar 

  2. Diaz-Ortiz, A.; Prieto, P.; Carrillo, J. R.; Martín, R; Torres, I. Curr. Org. Chem.2015, 19, 568.

    Article  CAS  Google Scholar 

  3. Maddila, S.; Pagadala, R.; Jonnalagadda, S. B. Lett. Org. Chem.2013, 10, 693.

    Article  CAS  Google Scholar 

  4. Kumar, R.; Yar, M. S.; Chaturvedi, S.; Srivastava, A. Int. J. PharmTech Res.2013, 5, 1844.

    CAS  Google Scholar 

  5. Sharma, J.; Ahmad, S.; Alam, M. S. J. Chem. Pharm. Res.2012, 4, 5157.

    CAS  Google Scholar 

  6. Al-Masoudi, I. A.; Al-Soud, Y. A.; Al-Salihi, N. J.; Al-Masoudi, N. A. Chem. Heterocycl. Compd. 2006, 42, 1377. [Khim. Geterotsikl. Soedin.2006, 1605.]

  7. El-Sherief, H. A. M; Youssif, B. G. M; Bukhari, S. N. A; Abdel-Aziz, M.; Abdel-Rahman, H. M. Bioorg. Chem.2018, 76, 314.

    Article  CAS  Google Scholar 

  8. Okada, H. US Patent 6194090B1.

  9. Oka, H; Joshi, R. V.; Tanabe, J.; Lahiri, S.; Vashi, D.; Ghogale, P. WO Patent 2006114377 A1.

  10. Srivastava, R.; Joshi, L. R. Phys. Chem. Chem. Phys.2014, 16, 17284.

    Article  CAS  Google Scholar 

  11. Moulin, A.; Bibian, M.; Blayo, A.-L.; El Habnouni, S.; Martinez, J.; Fehrentz, J.-A. Chem. Rev.2010, 110, 1809.

    Article  CAS  Google Scholar 

  12. Klingele, M. H.; Brooker, S. Eur. J. Org. Chem.2004, 3422.

  13. Lindstrom, J.; Johansson, M. H. Synth. Commun.2006, 36, 2217.

    Article  Google Scholar 

  14. Zhu, Y.; Olson, S. H.; Graham, D.; Patel, G.; Hermanowski-Vosatka, A.; Mundt, S.; Shah, K.; Springer, M.; Thieringer, R.; Wright, S.; Xiao, J.; Zokian, H.; Dragovic, J.; Balkovec, J. M. Bioorg. Med. Chem. Lett.2008, 18, 3412.

    Article  CAS  Google Scholar 

  15. Bechara, W. S.; Khazhieva, I. S.; Rodriguez, E.; Charette, A. B. Org. Lett.2015, 17, 1184.

    Article  CAS  Google Scholar 

  16. Kanaoka, Y.; Sato, E.; Yonemitsu, O.; Ban, Y. Tetrahedron Lett. 1964, 35, 2419.

    Article  Google Scholar 

  17. Kanaoka, Y.; Yonemitsu, O.; Tanizawa, K.; Ban, Y. Chem. Pharm. Bull. 1964, 12, 773.

    Article  CAS  Google Scholar 

  18. Schramm, G.; Grotsch, H; Pollmann, W. Angew. Chem., Int. Ed.1962, 1, 1.

    Article  Google Scholar 

  19. Yale, H. L.; Losee, K.; Martins, J.; Holsing, M.; Perry, F. M.; Bernstein, J. J. Am. Chem. Soc.1953, 75, 1933.

    Article  CAS  Google Scholar 

  20. Feng, H.; Leng. L.; Liu, J.; Tang, Y.; Tang. P.; Zhang, C.; Tang, X.; Jiao, S. Asian J. Chem.2013, 25, 4029.

    Article  CAS  Google Scholar 

  21. Fox, H. H.; Gibas, J. T. J. Org. Chem.1952, 17, 1653.

    Article  CAS  Google Scholar 

  22. Nesterova, E. Yu.; Voevudky, M. V.; Samukha, A. V.; Zubatyuk, R. I.; Shishkin, O. V. Chem. Heterocycl. Compd. 2005, 41, 1511. [Khim. Geterotsikl. Soedin.2005, 1834.]

  23. Horwitz, J. P.; Grakauskas, V. A. J. Org. Chem.1954, 19, 194.

    Article  CAS  Google Scholar 

  24. Larner, B. W.; Peters, A. T. J. Chem. Soc.1952, 680.

  25. Hsieh, J.-C.; Cheng, C.-H. Chem. Commun.2005, 36, 4554.

    Article  Google Scholar 

Download references

The work was carried out on the topic "“Design, fundamental research on the structure, properties, and mechanisms of the biological action of new small molecules and supramolecular systems to create innovative targeted drugs for the treatment of socially significant diseases” of the State Assignment of the Ministry of Science and Higher Education of the Russian Federation to Institute of Problems of Chemical Physics of the Russian Academy of Sciences (State registration number 0089-2019-0014).

Author information

Authors and Affiliations

  1. Institute of Problems of Chemical Physics of the Russian Academy of Sciences, 1 Akademika Semenova Ave., Chernogolovka, 142432, Moscow region, Russia

    Igor K. Yakuschenko, Natal’ya N. Pozdeeva & Svyatoslav Ya. Gadomsky

Authors
  1. Igor K. Yakuschenko
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Natal’ya N. Pozdeeva
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Svyatoslav Ya. Gadomsky
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Svyatoslav Ya. Gadomsky.

Additional information

Translated from Khimiya Geterotsiklicheskikh Soedinenii, 2019, 55(9), 834–838

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Yakuschenko, I.K., Pozdeeva, N.N. & Gadomsky, S.Y. A novel one-pot synthesis method of 3,4,5-triaryl-substituted 1,2,4-triazoles. Chem Heterocycl Comp 55, 834–838 (2019). https://doi.org/10.1007/s10593-019-02545-y

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10593-019-02545-y

Keywords

Search

Navigation