Skip to main content
SpringerLink
Log in

Green one-pot synthesis of 2H-indazolo[2,1-b]phthalazine-triones: a comparative study of heterogeneous solid acid catalysts with magnetic core

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

Abstract

The catalytic activity of four heterogeneous solid acid catalysts with magnetic core and sulfonic acid groups is evaluated and compared using one-pot three component synthesis of phthalazine-trione derivatives under solvent-free condition. The NiFe2O4 particles were selected as magnetic core, due to their enhanced chemical and magnetic stability. Furthermore, the desired products were obtained in excellent yields at short reaction times and environmentally friendly condition using the novel and reusable sulfonic acid grafted onto TiO2-coated nickel ferrite nanoparticles. This protocol avoids the use of expensive catalysts, toxic solvents and harsh reaction conditions.

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
Scheme 2
Fig. 4
Fig. 5
Fig. 6
Fig. 7
Fig. 8
Fig. 9
Fig. 10
Scheme 3
Fig. 11

Similar content being viewed by others

References

  1. L.-P. Liu, J.-M. Lu, M. Shi, Org. Lett. 9, 1303 (2007)

    Article  CAS  PubMed  Google Scholar 

  2. R. Ghahremanzadeh, G.I. Shakibaei, A. Bazgir, Synlett 2008, 1129 (2008)

    Article  CAS  Google Scholar 

  3. R. Ghahremanzadeh, S. Ahadi, M. Sayyafi, A. Bazgir, Tetrahedron Lett. 49, 4479 (2008)

    Article  CAS  Google Scholar 

  4. M.R. Nabid, S.J.T. Rezaei, R. Ghahremanzadeh, A. Bazgir, Ultrason. Sonochem. 17, 159 (2010)

    Article  CAS  PubMed  Google Scholar 

  5. S.S. El-Sakka, A. Soliman, A. Imam, Afinidad 66, 167 (2009)

    CAS  Google Scholar 

  6. N. Watanabe, Y. Kabasawa, Y. Takase, M. Matsukura, K. Miyazaki, H. Ishihara, K. Kodama, H. Adachi, J. Med. Chem. 41, 3367 (1998)

    Article  CAS  PubMed  Google Scholar 

  7. C.-K. Ryu, R.-E. Park, M.-Y. Ma, J.-H. Nho, Bioorg. Med. Chem. Lett. 17, 2577 (2007)

    Article  CAS  PubMed  Google Scholar 

  8. J. Li, Y.-F. Zhao, X.-Y. Yuan, J.-X. Xu, P. Gong, Molecules 11, 574 (2006)

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  9. J. Sinkkonen, V. Ovcharenko, K.N. Zelenin, I.P. Bezhan, B.A. Chakchir, F. Al-Assar, K. Pihlaja, Eur. J. Org. Chem. 2002, 2046 (2002)

    Article  Google Scholar 

  10. G. Hutchings, V. Polshettiwar, T. Asefa, Nanocatalysis: Synthesis and Applications (Wiley, New York, 2013)

    Google Scholar 

  11. A. Amoozadeh, S. Golian, S. Rahmani, RSC Adv. 5, 45974 (2015)

    Article  CAS  Google Scholar 

  12. M.B. Gawande, R. Luque, R. Zboril, ChemCatChem 6, 3312 (2014)

    Article  CAS  Google Scholar 

  13. H. Moghanian, A. Mobinikhaledi, A. Blackman, E. Sarough-Farahani, RSC Adv. 4, 28176 (2014)

    Article  CAS  Google Scholar 

  14. A. Mobinikhaledi, A.K. Amiri, J. Chem. Sci. 125, 1055 (2013)

    Article  CAS  Google Scholar 

  15. M.A. Bodaghifard, M. Hamidinasab, N. Ahadi, Curr. Org. Chem. 22, 234 (2018)

    Article  CAS  Google Scholar 

  16. D. Azarifar, O. Badalkhani, Y. Abbasi, M. Hasanabadi, J. Iran. Chem. Soc. 14, 403 (2017)

    Article  CAS  Google Scholar 

  17. S. Joshi, M. Kumar, S. Chhoker, G. Srivastava, M. Jewariya, V. Singh, J. Mol. Struct. 1076, 55 (2014)

    Article  CAS  Google Scholar 

  18. W.-F. Ma, Y. Zhang, L.-L. Li, L.-J. You, P. Zhang, Y.-T. Zhang, J.-M. Li, M. Yu, J. Guo, H.-J. Lu, ACS Nano 6, 3179 (2012)

    Article  CAS  PubMed  Google Scholar 

  19. M. Butterworth, L. Illum, S. Davis, Colloids Surf. A Physicochem. Eng. Asp. 179, 93 (2001)

    Article  CAS  Google Scholar 

  20. S. Santra, R. Tapec, N. Theodoropoulou, J. Dobson, A. Hebard, W. Tan, Langmuir 17, 2900 (2001)

    Article  CAS  Google Scholar 

  21. Y. Lu, Y. Yin, B.T. Mayers, Y. Xia, Nano Lett. 2, 183 (2002)

    Article  CAS  Google Scholar 

  22. A. Chaudhuri, M. Mandal, K. Mandal, J. Alloys Compd. 487, 698 (2009)

    Article  CAS  Google Scholar 

  23. F. Nemati, M.M. Heravi, R.S. Rad, Chin. J. Catal. 33, 1825 (2012)

    Article  CAS  Google Scholar 

  24. R. Sen, P. Jain, R. Patidar, S. Srivastava, R. Rana, N. Gupta, Mater. Today 2, 3750 (2015)

    Google Scholar 

  25. Z.-D. Li, H.-L. Wang, X.-N. Wei, X.-Y. Liu, Y.-F. Yang, W.-F. Jiang, J. Alloys Compd. 659, 240 (2016)

    Article  CAS  Google Scholar 

  26. K. Nejati, R. Zabihi, Chem. Cent. J. 6, 23 (2012)

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  27. H.S. Kim, D. Kim, B.S. Kwak, G.B. Han, M.-H. Um, M. Kang, Chem. Eng. J. 243, 272 (2014)

    Article  CAS  Google Scholar 

  28. K. Petcharoen, A. Sirivat, Mater. Sci. Eng. B 177, 421 (2012)

    Article  CAS  Google Scholar 

  29. Z. Zhang, Y. Liu, G. Yao, G. Zu, Y. Hao, Int. J. Appl. Ceram. Technol. 10, 142 (2013)

    Article  CAS  Google Scholar 

  30. F.M. Moghaddam, B.K. Foroushani, H.R. Rezvani, RSC Adv. 5, 18092 (2015)

    Article  CAS  Google Scholar 

  31. M. Sayyafi, M. Seyyedhamzeh, H.R. Khavasi, A. Bazgir, Tetrahedron 64, 2375 (2008)

    Article  CAS  Google Scholar 

  32. J.M. Khurana, D. Magoo, Tetrahedron Lett. 50, 7300 (2009)

    Article  CAS  Google Scholar 

  33. S.R. Konda, B.R. Reguri, M. Kagga, Der Pharma Chem. 6, 228 (2014)

    Google Scholar 

  34. K. Mazaahir, C. Ritika, J. Anwar, Chin. Sci. Bull. 57, 2273 (2012)

    Article  CAS  Google Scholar 

  35. R. Fazaeli, H. Aliyan, N. Fazaeli, Open Catal. J. 3, 14 (2010)

    Article  CAS  Google Scholar 

  36. R.A. Kiasat, A. Mouradezadegun, J.S. Saghanezhad, J. Serb. Chem. Soc. 78, 469 (2013)

    Article  CAS  Google Scholar 

  37. H.R. Shaterian, M. Ghashang, M. Feyzi, Appl. Catal. A Gen. 345, 128 (2008)

    Article  CAS  Google Scholar 

  38. A.A. Amiri, S. Javanshir, Z. Dolatkhah, M.G. Dekamin, New J. Chem. 39, 9665 (2015)

    Article  CAS  Google Scholar 

Download references

Acknowledgements

This work was supported by the research council of Arak University (Grant no. 9312432101). The authors acknowledge wholeheartedly the help received from colleague Dr. Mohammad Ali Bodaghifard from “Department of Chemistry”. There are no conflicts of interest to disclose.

Author information

Authors and Affiliations

  1. Department of Chemistry, Faculty of Science, Arak University, Arak, 38156-88138, Iran

    Mahdia Hamidinasab & Akbar Mobinikhaledi

  2. Institute of Nanosciences and Nanotechnology, Arak University, Arak, 38156-88138, Iran

    Mahdia Hamidinasab & Akbar Mobinikhaledi

Authors
  1. Mahdia Hamidinasab
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Akbar Mobinikhaledi
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Mahdia Hamidinasab.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Hamidinasab, M., Mobinikhaledi, A. Green one-pot synthesis of 2H-indazolo[2,1-b]phthalazine-triones: a comparative study of heterogeneous solid acid catalysts with magnetic core. J IRAN CHEM SOC 16, 1255–1263 (2019). https://doi.org/10.1007/s13738-019-01601-w

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s13738-019-01601-w

Keywords

Search

Navigation