Skip to main content
Log in

One-Pot Synthesis of Novel 3-Pyrazolyl-4H-1,2,4-triazoles Using Amino Glucose‐Functionalized Silica-Coated NiFe2O4 Nanoparticles as a Magnetically Separable Catalyst

  • Original Paper
  • Published:
Journal of Cluster Science Aims and scope Submit manuscript

Abstract

2-Amino glucose ((2S,3R,4S,5S,6R)-2-amino-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol) as a substrate for the synthesis of NiFe2O4@SiO n2 Pr@amino glucose supply an eco-friendly procedure for the synthesis of novel 3-pyrazolyl-4H-1,2,4-triazoles through a one-pot three-component reaction of semicarbazide (hydrazinecarboxamide), alcohol and synthetized pyrazolecarbaldehydes. NiFe2O4@SiO n2 Pr@amino glucose supply an environmentally friendly procedure for the synthesis of some of these compounds in high yields and short reaction times. The catalyst could be easily recovered and reused for six cycles with almost consistent activity. The structures of the synthesized 3-pyrazolyl-4H-1,2,4-triazole compounds were confirmed by 1H NMR, 13C NMR and FTIR spectral data and elemental analyses.

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.

Fig. 1
Fig. 2
Fig. 3
Fig. 4
Fig. 5
Fig. 6
Scheme 1
Scheme 2

Similar content being viewed by others

References

  1. K. S. Yeung and M. E. Farkas (2005). Tetrahedron Lett. 46, 3429.

    Article  CAS  Google Scholar 

  2. E. Huntsman, J. Balsells (2005). Eur. J. Org. Chem. 3761.

  3. D. V. Dolzhenko, D. M. Beal, B. T. Brown. D. Ellis, D. W. Gordon, S. P. Johnson, H. J. Mason, M. J. Ralph, T. J. Underwood and S. Wheeler (2008). Synlett. 2421.

  4. S. Ueda and H. Nagasawa (2009). J. Am. Chem. Soc. 131, 15080.

    Article  CAS  Google Scholar 

  5. P. Yin, P. W. B. Ma, Y. Chen, W. C. Huang, Y. Deng, and L. He (2009). Org. Lett. 11, 5482.

    Article  CAS  Google Scholar 

  6. M. R. Grimmett (1979). Comprehensive Org. Chem. 4, 357.

    CAS  Google Scholar 

  7. C. F. H. Allen (1946). Org. Synth. 26, 11.

    Article  CAS  Google Scholar 

  8. H. Fichtinger (1948). Natur. Suc. 36, 377.

    Google Scholar 

  9. M. Pesson, G. Polmanss, and S. Dupin (1959). Comp. Rend. 248, 1677.

    CAS  Google Scholar 

  10. M. Dobosz (1979). A Chem. 341, 163.

    Google Scholar 

  11. Y. Xu, M. Mclaughlin, E. N. Bolton, and R. A. Reamer (2010). J. Org. Chem. 75, 8666.

    Article  CAS  Google Scholar 

  12. M. Frederrigue, M. Reve, and B. Geo (1984). J. Heterocycl. Chem. 21, 1689.

    Article  Google Scholar 

  13. A. Reichelt, J. R. M. Rzasa, O. R. Thiel, M. Achmatowiez, R. D. Larsen, and D. Zhang (2010). Org. Lett. 12, 792.

    Article  CAS  Google Scholar 

  14. B. N. Goswami, J. C. S. Kataky, and J. N. Baruah (1984). J. Heterocycl. Chem. 21, 1225.

    Article  CAS  Google Scholar 

  15. A. Rezaei, A. Ramazani, F. Gouranlou, and W. J. Sang (2017). Lett. Org. Chem. 14, 86.

    Article  CAS  Google Scholar 

  16. S. T. Fardood, A. Ramazani, and S. Moradi (2017). J. Sol-Gel Sci. 82, 432.

    Article  CAS  Google Scholar 

  17. V. Polshettiwar and R. S. Varma (2010). Green Chem. 12, 743.

    Article  CAS  Google Scholar 

  18. A. Fihri, M. Bouhrara, B. Nekoueishahraki, J. M. Basset, and V. Polshettiwar (2011). Chem. Soc. Rev. 40, 5181.

    Article  CAS  Google Scholar 

  19. L. Zare Fekri, M. Nikpassand, S. Pourmirzajani, and B. Aghazadeh (2018). RSC Adv. 8, 22313.

    Article  Google Scholar 

  20. B. Aghazadeh and M. Nikpassand (2020). Carbohydr. Res. 483, 107755.

    Article  CAS  Google Scholar 

  21. M. Nikpassand, L. Zare Fekri, and P. Farokhian (2016). Ultrason. Sonochem. 28, 341.

    Article  CAS  Google Scholar 

  22. M. Nikpassand (2020). Dyes Pigm. 173, 107936.

    Article  CAS  Google Scholar 

  23. M. Nikpassand, L. Zare Fekri, L. Karimian, and M. Rassa (2015). Curr. Org. Synth. 12, 358.

    Article  CAS  Google Scholar 

  24. M. Nikpassand, L. Zare Fekri and S. Sanagou (2017). Dyes Pigm. 136, 140.

  25. M. Nikpassand and D. Pirdelzendeh (2016). Dyes Pigm. 130, 314.

    Article  CAS  Google Scholar 

Download references

Acknowledgments

Financial support by Rasht Branch, Islamic Azad University is gratefully acknowledged.

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to Mohammad Nikpassand.

Additional information

Publisher's Note

Springer Nature remains neutral with regard to jurisdictional claims in published maps and institutional affiliations.

Electronic supplementary material

Below is the link to the electronic supplementary material.

Supplementary material 1 (PDF 1488 kb)

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Nikpassand, M., Farshami, M.J. One-Pot Synthesis of Novel 3-Pyrazolyl-4H-1,2,4-triazoles Using Amino Glucose‐Functionalized Silica-Coated NiFe2O4 Nanoparticles as a Magnetically Separable Catalyst. J Clust Sci 32, 975–982 (2021). https://doi.org/10.1007/s10876-020-01855-y

Download citation

  • Received:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10876-020-01855-y

Keywords

Navigation