Skip to main content
Log in

SO3H-functionalized MCM-41 as an efficient catalyst for the combinatorial synthesis of 1H-pyrazolo-[3,4-b]pyridines and spiro-pyrazolo-[3,4-b]pyridines

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

Abstract

Sulfonic acid-functionalized (SO3H-functionalized) mesoporous MCM-41 catalyst was synthesized by anchoring 3-((3-(trimethoxysilyl)propyl)thio)propane-1-sulfonic acid onto MCM-41-type silica and characterized by FT-IR spectroscopy, elemental analysis and scanning electron microscopy (SEM) techniques. The catalyst was used for the efficient multi-component synthesis of 1H-pyrazolo-[3,4-b]pyridines and spiro-pyrazolo-[3,4-b]pyridines. Notably, the catalyst could be recycled and reused with negligible loss in activity over seven cycles.

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.

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

Similar content being viewed by others

References

  1. L.F. Tietze, A. Modi, Med. Res. Rev. 20, 304–322 (2000)

    Article  CAS  Google Scholar 

  2. I. Ugi, A. Dömling, W. Hörl, Endeavour 18, 115–122 (1994)

    Article  CAS  Google Scholar 

  3. A. Domling, Chem. Rev. 106, 17–89 (2006)

    Article  Google Scholar 

  4. K. Kumaravel, G. Vasuki, Curr. Org. Chem. 13, 1820–1841 (2009)

    Article  CAS  Google Scholar 

  5. M. Chiouaa, A. Samadia, E. Sorianoa, O. Lozachb, L. Meijerb, J. Marco-Contelles, Bioorgan. Med. Chem. Lett. 19, 4566–4569 (2009)

    Article  Google Scholar 

  6. D. Silva, M. Chioua, A. Samadi, M.C. Carreiras, M.-L. Jimeno, E. Mendes, C. de los Ríos, A. Romero, M. Villarroya, M.G. López, J. Marco-Contelles, Eur. J. Med. Chem. 46, 4676–4681 (2011)

    Article  CAS  Google Scholar 

  7. K. Wilcoxen, C.Q. Huang, J.R. McCarthy, D.E. Grigoriadis, C. Chen, Biorg. Med. Chem. Lett. 13, 3367–3370 (2003)

    Article  CAS  Google Scholar 

  8. T.E.S. Ali, Eur. J. Med. Chem. 44, 4385–4392 (2009)

    Article  Google Scholar 

  9. H. Hoehn, I. Polacek, E. Schulze, J. Med. Chem. 16, 1340–1346 (1973)

    Article  CAS  Google Scholar 

  10. K. Chavva, S. Pillalamarri, V. Banda, S. Gautham, J. Gaddamedi, P. Yedla, C.G. Kumar, N. Banda, Bioorg. Med. Chem. Lett. 23, 5893–5895 (2013)

    Article  CAS  Google Scholar 

  11. I.H. Eissa, A.M. El-Naggar, M.A. El-Hashash, Bioorg. Chem. 67, 43–56 (2016)

    Article  CAS  Google Scholar 

  12. Z. Yin, L. Yang, L. Wu, J. Chem. Sci. 125, 601–606 (2013)

    Article  CAS  Google Scholar 

  13. P. Rosenmunnd, M. Hosseini-Merescht, C. Bub, Liebigs Ann. Chem. 1994, 151–158 (1994)

    Article  Google Scholar 

  14. S. Crosignani, C. Jorand-Lebrun, P. Page, G. Campbell, V. Colovray, M. Missotten, Y. Humbert, C. Cleva, J.-F. Arrighi, M. Gaudet, Z. Johnson, P. Ferro, A. Chollet, A.C.S. Med, Chem. Lett. 2, 644–649 (2011)

    CAS  Google Scholar 

  15. T. Usui, M. Kondoh, C.-B. Cui, T. Mayumi, H. Osada, A. Tryprostatin, Biochem. J. 333, 543–548 (1998)

    Article  CAS  Google Scholar 

  16. A.J. Crisci, M.H. Tucker, M.-Y. Lee, S.G. Jang, J.A. Dumesic, S.L. Scott, ACS Catal. 1, 719–728 (2011)

    Article  CAS  Google Scholar 

  17. Q. Cai, W.Y. Lin, F.S. Xiao, W.Q. Pang, X.H. Chen, Microporous Mesoporous Mater. 8, 1–15 (1999)

    Article  Google Scholar 

  18. M. Cai, J. Peng, W. Hao, G. Ding, Green Chem. 13, 190–196 (2011)

    Article  CAS  Google Scholar 

  19. M. Selvaraj, P.K. Sinha, D.-W. Park, I. Kim, S. Kawi, C.S. Ha, Dalton Trans. 41, 14197–14203 (2012)

    Article  CAS  Google Scholar 

  20. S. Kawi, S.C. Shen, P.L. Chew, J. Mater. Chem. 12, 1582–1586 (2002)

    Article  CAS  Google Scholar 

  21. X. Sheng, J. Gao, L. Han, Y. Jia, W. Sheng, Microporous Mesoporous Mater. 143, 73–77 (2011)

    Article  CAS  Google Scholar 

  22. M. Hajjami, F. Ghorbani, F. Bakhti, Appl. Catal. A: Gen 470, 303–310 (2014)

    Article  CAS  Google Scholar 

  23. S. Safaei, I. Mohammadpoor-Baltork, A.R. Khosropour, M. Moghadam, S. Tangestaninejad, V. Mirkhani, Catal. Sci. Technol. 3, 2717–2722 (2013)

    Article  CAS  Google Scholar 

  24. S. Safaei, I. Mohammadpoor-Baltork, A.R. Khosropour, M. Moghadam, S. Tangestaninejad, V. Mirkhani, Adv. Synth. Catal. 345, 3095–3104 (2012)

    Article  Google Scholar 

  25. S. Safaei, I. Mohammadpoor-Baltork, A.R. Khosropour, M. Moghadam, S. Tangestaninejad, V. Mirkhani, R. Kia, RSC Adv. 2, 5610–5616 (2012)

    Article  CAS  Google Scholar 

Download references

Acknowledgements

The authors are grateful to the Centre of Excellence of Chemistry and Research Council of the University of Isfahan for financial support of this work.

Author information

Authors and Affiliations

Authors

Corresponding authors

Correspondence to Iraj Mohammadpoor-Baltork or Ahmad Reza Khosropour.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Safaei, S., Mohammadpoor-Baltork, I., Khosropour, A.R. et al. SO3H-functionalized MCM-41 as an efficient catalyst for the combinatorial synthesis of 1H-pyrazolo-[3,4-b]pyridines and spiro-pyrazolo-[3,4-b]pyridines. J IRAN CHEM SOC 14, 1583–1589 (2017). https://doi.org/10.1007/s13738-017-1099-8

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s13738-017-1099-8

Keywords

Navigation