Skip to main content
SpringerLink
Log in

Synthesis of some novel 4-amino-4H-1,2,4-triazole-3-thiol derivatives

  • Published:
Journal of the Iranian Chemical Society Aims and scope Submit manuscript

Abstract

A novel series of pyrazolyl[1,2,4]triazoles has been synthesized by the reaction of polyfunctionalized-triazole 1 with symmetric and asymmetric β-dicarbonyl compounds in ortho-phosphoric acid. Also, we found that the reaction between triazole 1 and arylidene malononitriles in DMF afforded Schiff base compounds 9a,b instead of the target pyrazolyl[1,2,4]triazole 8a,b. The same products 9a,b were synthesized via the reaction of triazole 1 with the corresponding aromatic aldehydes. Moreover, a new series of 6-methyl-6-aryl-5,6-dihydro[1,2,4]triazolo[4,3-b][1,2,4,5]tetrazine-3-thiol 11a,b and 9-amino-5-methyl-3,5-diphenyl-8-sulfanyl-2,4,5,9-tetrahydro-3H-[1,2,4]triazolo[5,1-c][1,2,4]triazepin-3-ol 12a has been successfully synthesized by the reaction of triazoles 1 with acetophenone derivatives.

Graphical abstract

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

Fig. 1
Scheme 1
Scheme 2
Scheme 3

Similar content being viewed by others

References

  1. L. Peyton, S. Gallagher, M. Hashemzadeh, Drugs Today 51, 705–718 (2015)

    Article  CAS  Google Scholar 

  2. S. Karakuş, U. Çoruh, B. Barlas-Durgun, M. Ezequiel, Ö. Suna, T. Vázquez-López, R. Sevim, Marmara Pharm. J. 14, 84–90 (2010)

    Article  Google Scholar 

  3. Y.A. Al-Soud, M.N. Al-Dweri, N.A. Al-Masoudi, II Farmaco 59, 775–783 (2004)

    Article  CAS  Google Scholar 

  4. A.R. Farghaly, E. De Clercq, H. El-Kashef, ARKIVOC 2006, 137–151 (2006)

    Article  Google Scholar 

  5. H. Abdel-Gawad, H.A. Mohamed, K.M. Dawood, F.A. Badria, Chem. Pharm. Bull. 58, 15–29 (2010)

    Article  Google Scholar 

  6. B. Zhang, Eur. J. Med. Chem. 168, 357–372 (2019)

    Article  CAS  PubMed  Google Scholar 

  7. S. Hussain, D. Kaushik, M. Sharma, Eur. J. Sci. Res. 5, 257–263 (2010)

    CAS  Google Scholar 

  8. S. Zhang, Z. Xu, C. Gao, Q.C. Ren, L. Chang, Z.S. Lv, L.S. Feng, Eur. J. Med. Chem. 138, 501–513 (2017)

    Article  CAS  PubMed  Google Scholar 

  9. Z. Li, Z. Gu, K. Yin, R. Zhang, Q. Deng, J. Xiang, Eur. J. Med. Chem. 44, 4716–4720 (2009)

    Article  CAS  PubMed  Google Scholar 

  10. M. Xu, Y. Peng, L. Zhu, S. Wang, J. Ji, K.P. Rakesh, Eur. J. Med. Chem. 180, 656–672 (2019)

    Article  CAS  PubMed  Google Scholar 

  11. J.M. Kane, M.W. Dudley, S.M. Sorensen, P.M. Francis, J. Med. Chem. 31, 1253–1258 (1988)

    Article  CAS  PubMed  Google Scholar 

  12. I. Khan, S. Ali, S. Hameed, N.H. Rama, M.T. Hussain, A. Wadood, R. Uddin, Z. Ul-Haq, A. Khan, S. Ali, M.I. Choudhary, Eur. J. Med. Chem. 45, 5200–5207 (2010)

    Article  CAS  PubMed  Google Scholar 

  13. X.M. Chu, C. Wang, W.L. Wang, L.L. Liang, W. Liu, K.K. Gong, K.L. Sun, Eur. J. Med. Chem. 166, 206–223 (2019)

    Article  CAS  PubMed  Google Scholar 

  14. J.N. Sangshetti, F.A. Khan, A.A. Kulkarni, R. Arote, R.H. Patil, RSC Adv. 5, 32376–32415 (2015)

    Article  CAS  Google Scholar 

  15. A. Manilal, B. Sabarathnam, G.S. Kiran, S. Sujith, C. Shakir, J. Selvin, Asian J. Med. Sci. 2, 195–200 (2010)

    CAS  Google Scholar 

  16. T. Akhtar, S. Hameed, K.M. Khan, A. Khan, M.I. Choudhary, J. Enzym. Inhib. Med. Chem. 25, 572–576 (2010)

    Article  CAS  Google Scholar 

  17. S. Ming-Xia, D. Xian-Qing, J. Enzym. Inhib. Med. Chem. 33, 453–478 (2018)

    Article  Google Scholar 

  18. M.Y. Mhasalkar, M.H. Shah, S.T. Nikam, J. Med. Chem. 14, 260–262 (1971)

    Article  CAS  PubMed  Google Scholar 

  19. D.M. Bailey, P.E. Hansen, A.G. Hlavac, E.R. Baizman, J. Pearl, A.F. Defelice, M.E. Feigenson, J. Med. Chem. 28, 256 (1985)

    Article  CAS  PubMed  Google Scholar 

  20. M. Wujec, M. Pitucha, M. Dobosz, U. Kosikowska, A. Malm, Acta Pharm. 54, 251–260 (2004)

    CAS  PubMed  Google Scholar 

  21. J.K. Sony, S. Ganguly, Int. J. Pham Pharm. Sci. 8, 75 (2016)

    Article  Google Scholar 

  22. O. Ebenezer, M. Shapi, J.A. Tuszynski, Biomedicines 10, 1124 (2022)

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  23. J.E. Queiroz, L.D. Dias, G.M.V. Verde, G.L.B. Aquino, A.J. Camargo, Curr. Org. Chem. 26, 81–90 (2022)

    Article  CAS  Google Scholar 

  24. N. Singh, S.K. Gupta, L. Tiwari, Int. J. Pharm. Erud. 11, 1–21 (2021)

    Google Scholar 

  25. H. Abdel-Rahman, J. Farghal, Chin. Chem. Soc. 51, 147–156 (2004)

    Article  Google Scholar 

  26. N. Gokhan-Kelekci, S. Yabanoglu, E. Kupeli, U. Salgin, O. Ozgen, G. Ucar, E. Yesilada, E. Kendi, A. Yesilada, A.A. Bilgin, Bioorg. Med. Chem. 15, 5775–5786 (2007)

    Article  PubMed  Google Scholar 

  27. S. Lee, B.P.J. Seung, Org. Lett. 11, 5214–5217 (2009)

    Article  CAS  PubMed  Google Scholar 

  28. R.B. Pathak, P.T. Chovatia, H.H. Parekh, Bioorg. Med. Chem. Lett. 22, 5129–5133 (2012)

    Article  CAS  PubMed  Google Scholar 

  29. A.M. Vijesh, A.M. Isloor, P. Shetty, S. Sundershan, H.K. Fun, Eur. J. Med. Chem. 62, 410–415 (2013)

    Article  CAS  PubMed  Google Scholar 

  30. H.H. Sayed, E.M.H. Morsy, E.M. Flefel, Synth. Commun. 40, 1360–1370 (2010)

    Article  CAS  Google Scholar 

  31. A.A. Amer, A.H. Moustafa, Synlett 27(11), 1703–1706 (2016)

    Article  CAS  Google Scholar 

  32. A.H. Moustafa, A.A. Amer, Synth. Commun. 47(11), 1102–1109 (2017)

    Article  CAS  Google Scholar 

  33. A.H. Moustafa, D.H. Ahmed, M.T. El-Wassimy, M.F. Mohamed, Synth. Commun. 51(4), 570–584 (2021)

    Article  CAS  Google Scholar 

  34. C.J. Parameshwara, S. Perugu, S. Ananthula, R.V. Rajeswar, J. Mol. Struct. 1225, 129140 (2021)

    Article  Google Scholar 

  35. H.N. Doğan, S. Büyüktimkin, S. Rollas, E. Yemni, A. Cevikbaş, Farmaco 52(8–9), 565–568 (1997)

    PubMed  Google Scholar 

  36. J.T. Mague, S.K. Mohamed, M. Akkurt, M.R. Albayati, Acta Crystallogr. Section E: Crystallogr. Commun. 71(6), o417 (2015)

    Article  CAS  Google Scholar 

  37. L.S. Philip, D. Balram, J. Heterocycl. Chem. 12(6), 1199–1205 (1975)

    Article  Google Scholar 

Download references

Acknowledgements

The authors acknowledge the Deanship of Scientific Research, Vice Presidency for Graduate Studies and Scientific Research at King Faisal University, Saudi Arabia, for financial support under the annual funding track (GRANT 5850).

Author information

Authors and Affiliations

  1. Department of Chemistry, College of Science, King Faisal University, 31982, Al-Ahsa, Saudi Arabia

    Mai M. Khalaf & Hany M. Abd El-Lateef

  2. Department of Chemistry, Faculty of Science, Sohag University, Sohag, 82524, Egypt

    Mai M. Khalaf, Hany M. Abd El-Lateef, Amer Anwar Amer & Amr Hassan Moustafa

  3. Faculty of Science, King Salman International University, RasSudr, Sinai, 46612, Egypt

    Amr Hassan Moustafa

Authors
  1. Mai M. Khalaf
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Hany M. Abd El-Lateef
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Amer Anwar Amer
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Amr Hassan Moustafa
    View author publications

    You can also search for this author in PubMed Google Scholar

Contributions

A.H.M. participated in the creation of the plan and helped with the writing, discussion, and article revision. A.A.A. initiated and planned the chemistry experiment, synthesized and characterized the samples, wrote the draft, and discussed the outcomes. M.M.K. and H.M.A. contributed to the idea of chemical experiments, discussing the results, and revising the paper. All authors reviewed the manuscript.

Corresponding authors

Correspondence to Hany M. Abd El-Lateef or Amr Hassan Moustafa.

Supplementary Information

Below is the link to the electronic supplementary material.

13738_2024_2997_MOESM1_ESM.docx

Full experimental detail, 1H, 13C NMR, and NOESY spectra for all new compounds 2-12. This material can be found through the “Supplementary Content” section of this article’s webpage.(DOCX 1426 KB)

Rights and permissions

Springer Nature or its licensor (e.g. a society or other partner) holds exclusive rights to this article under a publishing agreement with the author(s) or other rightsholder(s); author self-archiving of the accepted manuscript version of this article is solely governed by the terms of such publishing agreement and applicable law.

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Khalaf, M.M., El-Lateef, H.M.A., Amer, A.A. et al. Synthesis of some novel 4-amino-4H-1,2,4-triazole-3-thiol derivatives. J IRAN CHEM SOC 21, 1291–1297 (2024). https://doi.org/10.1007/s13738-024-02997-w

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s13738-024-02997-w

Keywords

Search

Navigation