Skip to main content
SpringerLink
Log in

Click synthesis of 1,4-disubstituted-1,2,3-triazoles catalyzed by melamine-supported CuO nanoparticles as an efficient recyclable catalyst in water

  • Published:
Research on Chemical Intermediates Aims and scope Submit manuscript

Abstract

Melamine-supported CuO nanoparticles (M-CuO nanocatalyst) are prepared as a new and efficient recyclable nanocatalyst for the regioselective synthesis of 1,2,3-triazoles in water. This new nanocatalyst was prepared by co-precipitation method and characterized by FT-IR spectral study, TGA, DSC, XRF, ICP-OES, XRD, SEM, EDS and BET analysis. A wide range of 1,4-disubstituted-1,2,3-triazoles were synthesized from reaction of benzyl halides or alkyl halides with phenyl acetylene and sodium azide in high yields. M-CuO nanocatalyst could be reused more than 6 times without considerable loss of its initial activity.

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

Scheme 1
Fig. 1
Fig. 2
Fig. 3
Fig. 4
Scheme 2

Similar content being viewed by others

References

  1. S. Kantheti, R. Narayan, K.V.S.N. Raju, P.S. Sarath, R. Narayan, K.V.S.N. Raju, RSC. Adv. 5, 3687 (2015)

    Article  CAS  Google Scholar 

  2. Y. Xia, Z. Fan, J. Yao, Q. Liao, W. Li, F. Qu, L. Peng, Bioorg. Med. Chem. Lett. 16, 2693 (2006)

    Article  CAS  Google Scholar 

  3. R. Huisgen, Pure Appl. Chem. 61, 613 (1986)

    Article  Google Scholar 

  4. R. Huisgen, Angew. Chem. 75, 604 (1963)

    Article  CAS  Google Scholar 

  5. K. Gonzales-Silva, D. Rendon-Nava, A. Alvarez-Hernández, D. Mendoza-Espinosa, New J. Chem. 43, 16538 (2019)

    Article  Google Scholar 

  6. H. Naeimi, S. Dadashzadeh, M. Moradian, Res. Chem. Intermed. 41, 2687 (2015)

    Article  CAS  Google Scholar 

  7. C. Sharma, M. Kaur, A. Choudhary, S. Sharma, S. Paul, Catal. Lett. 159, 82 (2020)

    Article  Google Scholar 

  8. A. Pathigoola, R.P. Pola, K.M. Sureshan, Appl. Catal A Gen. 453, 151 (2013)

    Article  Google Scholar 

  9. V.D. da Silva, B.M. de Faria, E. Colombo, L. Ascari, G.P.A. Freitas, L.S. Flores, Y. Cordeiro, L. Romão, C.D. Buarque, Bioorg. Chem. 83, 87 (2019)

    Article  Google Scholar 

  10. M. Gholinejad, E. Oftadeh, J.M. Sansano, ChemistrySelect 4, 3151 (2019)

    Article  CAS  Google Scholar 

  11. M. Shabber, A.K. Padala, B.A. Dar, B. Singh, B. Sreedhar, R.A. Vishwakarma, S.B. Bharate, Tetrahedron 68, 8156 (2012)

    Article  Google Scholar 

  12. F. Faeghi, S. Javanshir, S. Molaei, Appl. Organomet. Chem. 3, 11427 (2018)

    CAS  Google Scholar 

  13. N. Touj, I. Özdemir, S. Yasar, N. Hamdi, Inorg. Chim. Acta 467, 21 (2017)

    Article  CAS  Google Scholar 

  14. A.R. Hajipour, M. Karimzadeh, F. Fakhari, H. Karimi, Appl. Organomet. Chem. 30, 964 (2016)

    Google Scholar 

  15. S. Bahadorikhalili, L. Ma’mani, H. Mahdavi, A. Shafiee, Microporous Mesoporous Mater. 262, 207 (2018)

    Article  CAS  Google Scholar 

  16. N. Touj, A. Chakchouk-Mtibaa, L. Mansour, A.H. Harrath, J.H. Al-Tamimi, I. Özdemir, L. Mellouli, S. Yaşar, N. Hamdi, J. Organomet. Chem. 853, 49 (2017)

    Article  CAS  Google Scholar 

  17. M. Kumari, Y. Jain, P. Yadav, H. Laddha, R. Gupta, Catal. Lett. 149, 2180 (2019)

    Article  CAS  Google Scholar 

  18. M. Tajbakhsh, M. Farhang, S.M. Baghbanian, R. Hosseinzadeh, M. Tajbakhsh, New J. Chem. 39, 1827 (2015)

    Article  CAS  Google Scholar 

  19. A. Keivanloo, M. Bakherad, M. Khosrojerdi, A.H. Amin, Res. Chem. Intermed. 44, 2571 (2018)

    Article  CAS  Google Scholar 

  20. A.R. Sardarian, F. Mohammadi, M. Esmaeilpour, Res. Chem. Intermed. 45, 1437 (2019)

    Article  CAS  Google Scholar 

  21. M.A. Karimi Zarchi, F. Nazem, J. Iran. Chem. Soc. 11, 1731 (2014)

    Article  CAS  Google Scholar 

  22. M. Keshavarz, R. Badri, Mol. Divers. 15, 957 (2011)

    Article  CAS  Google Scholar 

  23. A. Coelho, P. Diz, O. Caamaño, E. Sotelo, Adv. Synth. Catal. 352, 1179 (2010)

    Article  CAS  Google Scholar 

  24. U. Sirion, Y.J. Bae, B.S. Lee, D.Y. Chi, Synlett. 2008, 2326 (2008)

    Article  Google Scholar 

  25. H. Naeimi, R. Shaabani, Catal. Commun. 87, 6 (2016)

    Article  CAS  Google Scholar 

  26. B. Gerard, J. Ryan, A.B. Beeler, J.A. Porco, Tetrahedron 62, 6405 (2006)

    Article  CAS  Google Scholar 

  27. J. Albadi, A. Alihosseinzadeh, A. Mansournezhad, Synth. Commun. 45, 877 (2015)

    Article  CAS  Google Scholar 

  28. Z. Sotoudehnia, J. Albadi, A.R. Momeni, Appl. Organomet. Chem. 33, e4625 (2019)

    Article  Google Scholar 

  29. J. Albadi, A. Alihoseinzadeh, M. Jalali, M. Shahrezaei, A. Mansournezhad, Mol. Catal. 440, 133 (2017)

    Article  CAS  Google Scholar 

  30. J. Albadi, A. Alihosseinzadeh, A. Mansournezhad, Acta Chim. Slov. 62, 617 (2015)

    Article  CAS  Google Scholar 

  31. J. Albadi, A. Mansournezhad, Res. Chem. Intermed. 42, 5739 (2016)

    Article  CAS  Google Scholar 

  32. X. Wen, W. Zhang, S. Yang, Langmuir 19, 5898 (2003)

    Article  CAS  Google Scholar 

  33. N. Kanagatha, N. Sivakumar, K. Gayathri, P. Krishnan, N.G. Renganathan, S. Gunasekaran, G. Anbalagan, Proc. Indian Natl. Sci. Acad. 79, 467 (2013)

    Google Scholar 

  34. E.W. Hughes, J. Am. Chem. Soc. 63, 1737 (1941)

    Article  CAS  Google Scholar 

  35. V. Vellora, T. Padil, M. Cernik, Int. J. Nanomed. 8, 889 (2013)

    Google Scholar 

  36. J. Albadi, M. Jalali, A.R. Momeni, Res. Chem. Intermed. 44, 2395 (2018)

    Article  CAS  Google Scholar 

Download references

Acknowledgements

We are thankful to the Shahrekord University for the support of this work.

Author information

Authors and Affiliations

  1. Department of Chemistry, Faculty of Science, Shahrekord University, Shahrekord, Iran

    Mahboobeh Rajabi, Jalal Albadi & Ahmadreza Momeni

Authors
  1. Mahboobeh Rajabi
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Jalal Albadi
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Ahmadreza Momeni
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Jalal Albadi.

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 (DOCX 1001 kb)

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Rajabi, M., Albadi, J. & Momeni, A. Click synthesis of 1,4-disubstituted-1,2,3-triazoles catalyzed by melamine-supported CuO nanoparticles as an efficient recyclable catalyst in water. Res Chem Intermed 46, 3879–3889 (2020). https://doi.org/10.1007/s11164-020-04178-9

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11164-020-04178-9

Keywords

Search

Navigation