Skip to main content
SpringerLink
Log in

Ni-guanidine@MCM-41 NPs: a new catalyst for the synthesis of 4,4ʹ-(arylmethylene)-bis-(3-methyl-1-phenyl-1H-pyrazol-5-ols) and symmetric di-aryl sulfides

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

Abstract

In this work, the surface of mesoporous MCM-41 was modified with guanidine, and then, Nickel particles have become immobilized on its surface (Ni-guanidine@MCM-41NPs). This heterogeneous catalyst has been identified by various techniques including: low-angle X-ray diffraction, scanning electron microscopy, energy-dispersive X-ray spectroscopy, inductively coupled plasma, thermal gravimetric analysis and N2 adsorption–desorption measurement isotherms, and its catalytic application was studied in the synthesis of 4,4ʹ-(arylmethylene)-bis-(3-methyl-1-phenyl-1H-pyrazol-5-ol) derivatives and symmetric di-aryl sulfides. The prepared organometallic complex could be isolated, post-reaction, by simple filtration for several consecutive cycles without a notable change in its catalytic 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
Scheme 2
Scheme 3
Fig. 1
Fig. 2
Fig. 3
Fig. 4
Fig. 5
Fig. 6

Similar content being viewed by others

References

  1. C.M. Marson, Chem. Soc. Rev. 41, 7712 (2012)

    CAS  PubMed  Google Scholar 

  2. B. Jiang, T. Rajale, W. Wever, S.J. Tu, G. Li, Chem. Asian J. 5, 2318 (2010)

    CAS  PubMed  Google Scholar 

  3. A. Dömling, W. Wang, K. Wang, Chem. Rev. 112, 3083 (2012)

    PubMed  PubMed Central  Google Scholar 

  4. A. Ghorbani-Choghamarani, M. Mohammadi, T. Tamoradi, M. Ghadermazi, Polyhedron 158, 25 (2019)

    CAS  Google Scholar 

  5. H. Wu, Y. Gou, J. Wang, L. Tao, Macromol. Rapid Commun. 39, 1800064 (2018)

    Google Scholar 

  6. D. Das, ChemistrySelect 1, 1959 (2016)

    CAS  Google Scholar 

  7. C. Shen, X.F. Wu, Chem. Eur. J. 23, 2973 (2017)

    CAS  PubMed  Google Scholar 

  8. R.N. Mahajan, F.H. Havaldar, P.S. Fernandes, J. Indian Chem. Soc. 68, 245 (1991)

    CAS  Google Scholar 

  9. P.M.S. Chauhan, S. Singh, R.K. Chatterjee, ChemInform 24, 72 (1993)

    Google Scholar 

  10. M. Keshavarz, M. Vafaei-Nezhad, Catal. Lett. 146, 353 (2016)

    CAS  Google Scholar 

  11. M. Baghernejad, K. Niknam, Int. J. Chem. 4, 52 (2012)

    CAS  Google Scholar 

  12. C.S. Yao, C.X. Yu, S.J. Tu, D.Q. Shi, X.S. Wang, Y.Q. Zhu, H.Z. Yang, J. Fluor. Chem. 128, 105 (2007)

    CAS  Google Scholar 

  13. A.R. Moosavi-Zare, M.A. Zolfigol, M. Zarei, A. Zare, V. Khakyzadeh, A. Hasaninejad, Appl. Catal. A Gen. 467, 61 (2013)

    CAS  Google Scholar 

  14. M.N. Elinson, A.S. Dorofeev, R.F. Nasybullin, G.I. Nikishin, Synthesis (Stuttg) 2008, 1933 (2008)

    Google Scholar 

  15. K. Niknam, D. Saberi, M. Sadegheyan, A. Deris, Tetrahedron Lett. 51, 692 (2010)

    CAS  Google Scholar 

  16. E. Soleimani, S. Ghorbani, M. Taran, A. Sarvary, Comptes Rendus Chim. 15, 955 (2012)

    CAS  Google Scholar 

  17. A. Hasaninejad, M. Shekouhy, A. Zare, S.M.S.H. Ghattali, N. Golzar, J. Iran. Chem. Soc. 8, 411 (2011)

    CAS  Google Scholar 

  18. K. Niknam, M.S. Habibabad, A. Deris, N. Aeinjamshid, Chem. Mon. 144, 987 (2013)

    CAS  Google Scholar 

  19. K. Niknam, S. Mirzaee, Synth. Commun. 41, 2403 (2011)

    CAS  Google Scholar 

  20. Y. Zhang, K.C. Ngeow, J.Y. Ying, Org. Lett. 9, 3495 (2007)

    CAS  PubMed  Google Scholar 

  21. I.P. Beletskaya, V.P. Ananikov, Chem. Rev. 111, 1596 (2011)

    CAS  PubMed  Google Scholar 

  22. L. Chen, A. Noory Fajer, Z. Yessimbekov, M. Kazemi, M. Mohammadi, J. Sulfur Chem. 40, 451 (2019)

    CAS  Google Scholar 

  23. L. Rout, T.K. Sen, T. Punniyamurthy, Angew. Chem. Int. Ed. 46, 5583 (2007)

    CAS  Google Scholar 

  24. M. Moorthy, A. Govindaraj, B. Madheswaran, B. Kannan, R. Rangappan, ChemistrySelect 1, 4833 (2016)

    CAS  Google Scholar 

  25. D. Giuliani, A. Ottani, D. Zaffe, M. Galantucci, F. Strinati, R. Lodi, S. Guarini, Neurobiol. Learn. Mem. 104, 82 (2013)

    CAS  PubMed  Google Scholar 

  26. L. Argueta-Figueroa, O. Martínez-Alvarez, J. Santos-Cruz, R. Garcia-Contreras, L.S. Acosta-Torres, J. de la Fuente-Hernández, M.C. Arenas-Arrocena, Mater. Sci. Eng. C 76, 1305 (2017)

    CAS  Google Scholar 

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

    CAS  Google Scholar 

  28. A. Ghorbani-Choghamarani, M. Mohammadi, Z. Taherinia, J. Iran. Chem. Soc. 16, 411 (2019)

    CAS  Google Scholar 

  29. M. Nikoorazm, A. Ghorbani-Choghamaranai, M. Khanmoradi, P. Moradi, J. Porous Mater. 25, 1831 (2018)

    CAS  Google Scholar 

  30. H. Filian, A. Ghorbani-Choghamarani, E. Tahanpesar, J. Porous Mater. (2018) (in press)

  31. N. Gutta, V.K. Velisoju, A. Chatla, V. Boosa, J. Tardio, J. Patel, V. Akula, Energy Fuels 32, 4008 (2018)

    CAS  Google Scholar 

  32. G. Maria, A.I. Stoica, I. Luta, D. Stirbet, G.L. Radu, Microporous Mesoporous Mater. 162, 80 (2012)

    CAS  Google Scholar 

  33. A. Benhamou, J.P. Basly, M. Baudu, Z. Derriche, R. Hamacha, J. Colloid Interface Sci. 404, 135 (2013)

    CAS  PubMed  Google Scholar 

  34. A.G. Thomé, F. Schroeter, P. Bottke, J. Wittayakun, F. Roessner, Microporous Mesoporous Mater. 274, 342 (2019)

    Google Scholar 

  35. S.A. Idris, S.R. Harvey, L.T. Gibson, J. Hazard. Mater. 193, 171 (2011)

    CAS  PubMed  Google Scholar 

  36. Y. Sun, X.W. Liu, W. Su, Y. Zhou, L. Zhou, Appl. Surf. Sci. 253, 5650 (2007)

    CAS  Google Scholar 

  37. M. Abdollahi-Alibeik, M. Pouriayevali, Catal. Commun. 22, 13 (2012)

    CAS  Google Scholar 

  38. X. Wang, G. Wu, J. Li, N. Zhao, W. Wei, Y. Sun, J. Mol. Catal. A: Chem. 276, 86 (2007)

    CAS  Google Scholar 

  39. Y. Huang, W. Hao, G. Ding, M.Z. Cai, J. Organomet. Chem. 715, 141 (2012)

    CAS  Google Scholar 

  40. B. Karami, M. Farahi, S. Akrami, D. Elhamifar, New J. Chem. 42, 12811 (2018)

    CAS  Google Scholar 

  41. M. Eslami, M.G. Dekamin, L. Motlagh, A. Maleki, Green Chem. Lett. Rev. 11, 36 (2018)

    CAS  Google Scholar 

  42. J.N. Appaturi, M. Selvaraj, S.B. Abdul Hamid, M.R. Bin Johan, Microporous Mesoporous Mater. 260, 260 (2018)

    CAS  Google Scholar 

  43. T. Tamoradi, M. Ghadermazi, A. Ghorbani-Choghamarani, Catal. Lett. 148, 857 (2018)

    CAS  Google Scholar 

  44. A. Ghorbani-Choghamarani, Z. Seydyosefi, B. Tahmasbi, Appl. Organomet. Chem. 32, e4396 (2018)

    Google Scholar 

Download references

Acknowledgements

This work was supported by the research facilities of Ahvaz Branch, Islamic Azad University, Ahvaz, Iran.

Author information

Authors and Affiliations

  1. Department of Chemistry, Khuzestan Science and Research Branch, Islamic Azad University, Ahvaz, Iran

    Hossein Filian

  2. Department of Chemistry, Ahvaz Branch, Islamic Azad University, Ahvaz, Iran

    Hossein Filian & Elham Tahanpesar

  3. Department of Chemistry, Faculty of Science, Ilam University, P.O. Box 69315516, Ilam, Iran

    Arash Ghorbani-Choghamarani

Authors
  1. Hossein Filian
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Arash Ghorbani-Choghamarani
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Elham Tahanpesar
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Arash Ghorbani-Choghamarani.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Filian, H., Ghorbani-Choghamarani, A. & Tahanpesar, E. Ni-guanidine@MCM-41 NPs: a new catalyst for the synthesis of 4,4ʹ-(arylmethylene)-bis-(3-methyl-1-phenyl-1H-pyrazol-5-ols) and symmetric di-aryl sulfides. J IRAN CHEM SOC 16, 2673–2681 (2019). https://doi.org/10.1007/s13738-019-01727-x

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s13738-019-01727-x

Keywords

Search

Navigation