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

  • Mahdia HamidinasabEmail author
  • Akbar Mobinikhaledi
Original Paper


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.


Phthalazine-trione Multicomponent reaction Magnetic nanoparticles Heterogeneous catalysis Hybrid materials Green condition 



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.


  1. 1.
    L.-P. Liu, J.-M. Lu, M. Shi, Org. Lett. 9, 1303 (2007)CrossRefGoogle Scholar
  2. 2.
    R. Ghahremanzadeh, G.I. Shakibaei, A. Bazgir, Synlett 2008, 1129 (2008)CrossRefGoogle Scholar
  3. 3.
    R. Ghahremanzadeh, S. Ahadi, M. Sayyafi, A. Bazgir, Tetrahedron Lett. 49, 4479 (2008)CrossRefGoogle Scholar
  4. 4.
    M.R. Nabid, S.J.T. Rezaei, R. Ghahremanzadeh, A. Bazgir, Ultrason. Sonochem. 17, 159 (2010)CrossRefGoogle Scholar
  5. 5.
    S.S. El-Sakka, A. Soliman, A. Imam, Afinidad 66, 167 (2009)Google Scholar
  6. 6.
    N. Watanabe, Y. Kabasawa, Y. Takase, M. Matsukura, K. Miyazaki, H. Ishihara, K. Kodama, H. Adachi, J. Med. Chem. 41, 3367 (1998)CrossRefGoogle Scholar
  7. 7.
    C.-K. Ryu, R.-E. Park, M.-Y. Ma, J.-H. Nho, Bioorg. Med. Chem. Lett. 17, 2577 (2007)CrossRefGoogle Scholar
  8. 8.
    J. Li, Y.-F. Zhao, X.-Y. Yuan, J.-X. Xu, P. Gong, Molecules 11, 574 (2006)CrossRefGoogle Scholar
  9. 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)CrossRefGoogle Scholar
  10. 10.
    G. Hutchings, V. Polshettiwar, T. Asefa, Nanocatalysis: Synthesis and Applications (Wiley, New York, 2013)Google Scholar
  11. 11.
    A. Amoozadeh, S. Golian, S. Rahmani, RSC Adv. 5, 45974 (2015)CrossRefGoogle Scholar
  12. 12.
    M.B. Gawande, R. Luque, R. Zboril, ChemCatChem 6, 3312 (2014)CrossRefGoogle Scholar
  13. 13.
    H. Moghanian, A. Mobinikhaledi, A. Blackman, E. Sarough-Farahani, RSC Adv. 4, 28176 (2014)CrossRefGoogle Scholar
  14. 14.
    A. Mobinikhaledi, A.K. Amiri, J. Chem. Sci. 125, 1055 (2013)CrossRefGoogle Scholar
  15. 15.
    M.A. Bodaghifard, M. Hamidinasab, N. Ahadi, Curr. Org. Chem. 22, 234 (2018)CrossRefGoogle Scholar
  16. 16.
    D. Azarifar, O. Badalkhani, Y. Abbasi, M. Hasanabadi, J. Iran. Chem. Soc. 14, 403 (2017)CrossRefGoogle Scholar
  17. 17.
    S. Joshi, M. Kumar, S. Chhoker, G. Srivastava, M. Jewariya, V. Singh, J. Mol. Struct. 1076, 55 (2014)CrossRefGoogle Scholar
  18. 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)CrossRefGoogle Scholar
  19. 19.
    M. Butterworth, L. Illum, S. Davis, Colloids Surf. A Physicochem. Eng. Asp. 179, 93 (2001)CrossRefGoogle Scholar
  20. 20.
    S. Santra, R. Tapec, N. Theodoropoulou, J. Dobson, A. Hebard, W. Tan, Langmuir 17, 2900 (2001)CrossRefGoogle Scholar
  21. 21.
    Y. Lu, Y. Yin, B.T. Mayers, Y. Xia, Nano Lett. 2, 183 (2002)CrossRefGoogle Scholar
  22. 22.
    A. Chaudhuri, M. Mandal, K. Mandal, J. Alloys Compd. 487, 698 (2009)CrossRefGoogle Scholar
  23. 23.
    F. Nemati, M.M. Heravi, R.S. Rad, Chin. J. Catal. 33, 1825 (2012)CrossRefGoogle Scholar
  24. 24.
    R. Sen, P. Jain, R. Patidar, S. Srivastava, R. Rana, N. Gupta, Mater. Today 2, 3750 (2015)CrossRefGoogle Scholar
  25. 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)CrossRefGoogle Scholar
  26. 26.
    K. Nejati, R. Zabihi, Chem. Cent. J. 6, 23 (2012)CrossRefGoogle Scholar
  27. 27.
    H.S. Kim, D. Kim, B.S. Kwak, G.B. Han, M.-H. Um, M. Kang, Chem. Eng. J. 243, 272 (2014)CrossRefGoogle Scholar
  28. 28.
    K. Petcharoen, A. Sirivat, Mater. Sci. Eng. B 177, 421 (2012)CrossRefGoogle Scholar
  29. 29.
    Z. Zhang, Y. Liu, G. Yao, G. Zu, Y. Hao, Int. J. Appl. Ceram. Technol. 10, 142 (2013)CrossRefGoogle Scholar
  30. 30.
    F.M. Moghaddam, B.K. Foroushani, H.R. Rezvani, RSC Adv. 5, 18092 (2015)CrossRefGoogle Scholar
  31. 31.
    M. Sayyafi, M. Seyyedhamzeh, H.R. Khavasi, A. Bazgir, Tetrahedron 64, 2375 (2008)CrossRefGoogle Scholar
  32. 32.
    J.M. Khurana, D. Magoo, Tetrahedron Lett. 50, 7300 (2009)CrossRefGoogle Scholar
  33. 33.
    S.R. Konda, B.R. Reguri, M. Kagga, Der Pharma Chem. 6, 228 (2014)Google Scholar
  34. 34.
    K. Mazaahir, C. Ritika, J. Anwar, Chin. Sci. Bull. 57, 2273 (2012)CrossRefGoogle Scholar
  35. 35.
    R. Fazaeli, H. Aliyan, N. Fazaeli, Open Catal. J. 3, 14 (2010)CrossRefGoogle Scholar
  36. 36.
    R.A. Kiasat, A. Mouradezadegun, J.S. Saghanezhad, J. Serb. Chem. Soc. 78, 469 (2013)CrossRefGoogle Scholar
  37. 37.
    H.R. Shaterian, M. Ghashang, M. Feyzi, Appl. Catal. A Gen. 345, 128 (2008)CrossRefGoogle Scholar
  38. 38.
    A.A. Amiri, S. Javanshir, Z. Dolatkhah, M.G. Dekamin, New J. Chem. 39, 9665 (2015)CrossRefGoogle Scholar

Copyright information

© Iranian Chemical Society 2019

Authors and Affiliations

  1. 1.Department of Chemistry, Faculty of ScienceArak UniversityArakIran
  2. 2.Institute of Nanosciences and NanotechnologyArak UniversityArakIran

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