Advertisement

Research on Chemical Intermediates

, Volume 46, Issue 1, pp 179–195 | Cite as

Ferric (III) complex supported on superparamagnetic Fe3O4@SiO2 as a reusable Lewis acid catalyst: a new highly efficient protocol for the synthesis of acridinedione and spiroquinazolin-4(3H)-one derivatives

  • Hadi MohammadiEmail author
  • Hamid Reza Shaterian
Article
  • 45 Downloads

Abstract

Nano-Fe3O4@SiO2-3,4-dihydroxybenzaldehyde/barbituric acid/phthalhydrazide-FeCl3 (nano-Fe3O4@SiO2-HBP-FeCl3) was prepared and authenticated by usual analytical and spectroscopic techniques. The prepared nano-Fe3O4@SiO2-HBP-FeCl3 was applied to acridinedione and spiroquinazolin-4(3H)-one derivatives under green conditions. In addition, this research offers several advantages such as very easy reaction conditions, simple work-up, excellent yields, high purity of the desired product, short reaction time and one-pot reaction to synthesize Fe3O4@SiO2-HBP-FeCl3. The recycling studies revealed that catalyst could be easily recovered using an external magnet and reused five times without significant loss of its catalytic activity.

Keywords

Nano-Fe3O4@SiO2-HBP-FeCl3 Superparamagnetic nanocatalyst Green synthesis Acridinediones Spiroquinazolin-4(3H)-ones 

Notes

Acknowledgements

We gratefully appreciate the University of Sistan and Baluchestan Research Councils for the financial support of this work.

Supplementary material

11164_2019_3942_MOESM1_ESM.docx (775 kb)
Supplementary material 1 (DOCX 775 kb)

References

  1. 1.
    Z. Nasresfahani, M.Z. Kassaee, E. Eidi, Appl. Organomet. Chem. 31, e3800 (2017)Google Scholar
  2. 2.
    P. Kumar, K. Kadyan, M. Duhan, J. Sindhu, K. Hussain, S. Lal, Chem. Pap. 73, 1153 (2019)Google Scholar
  3. 3.
    R.K. Sharma, M. Yadav, M.B. Gawande, ACS Symp. Ser. 1238, 1 (2016)Google Scholar
  4. 4.
    S. Gandhi, N. Nagalakshmi, I. Baskaran, V. Dhanalakshmi, M.R. Gopinathan, N.R. Anbarasan, J. Appl. Polym. Sci. 118, 1666 (2010)Google Scholar
  5. 5.
    T. Demirci, B. Çelik, Y. Yıldız, S. Eriş, M. Arslan, F. Sen, B. Kilbas, RSC Adv. 6, 76948 (2016)Google Scholar
  6. 6.
    E. Esma, Y. Yunus, K. Benan, Ş. Fatih, J. Nanosci. Nanotechnol. 16, 5944 (2016)Google Scholar
  7. 7.
    F. Şen, G. Gökağaç, S. Şen, J. Nanopart. Res. 15, 1979 (2013)Google Scholar
  8. 8.
    R. Ayranci, G. Baskaya, M. Guzel, S. Bozkurt, M. Ak, A. Savk, F. Sen, Nano-Struct. Nano-Objects 11, 13 (2017)Google Scholar
  9. 9.
    Y. Yildiz, T.O. Okyay, B. Sen, B. Gezer, S. Kuzu, A. Savk, E. Demir, Z. Dasdelen, H. Sert, F. Sen, ChemistrySelect 2, 697 (2017)Google Scholar
  10. 10.
    Z. Tai, M.A. Isaacs, L.J. Durndell, C.M.A. Parlett, A.F. Lee, K. Wilson, Mol. Catal. 449, 137 (2018)Google Scholar
  11. 11.
    A. Mirhashemi, M.A. Amrollahi, Res. Chem. Intermed. 45, 2549 (2019)Google Scholar
  12. 12.
    M.M. Khodaei, A. Alizadeh, M. Haghipour, Res. Chem. Intermed. 45, 2727 (2019)Google Scholar
  13. 13.
    M. Gholamhosseini-Nazari, S. Esmati, K.D. Safa, A. Khataee, R. Teimuri-Mofrad, Res. Chem. Intermed. 45, 1841 (2019)Google Scholar
  14. 14.
    S.V. Sokolov, E. Kätelhön, R.G. Compton, J. Phys. Chem. C 119, 25093 (2015)Google Scholar
  15. 15.
    M.F. Silva, A.A.W. Hechenleitner, J.M. Irache, A.J.A. de Oliveira, E.A.G. Pineda, J. Mater. Sci. 18, 1400 (2015)Google Scholar
  16. 16.
    V. Polshettiwar, R.S. Varma, Green Chem. 12, 743 (2010)Google Scholar
  17. 17.
    R.N. Baig, R.S. Varma, Chem. Commun. 48, 6220 (2012)Google Scholar
  18. 18.
    M. Sheykhan, A. Yahyazadeh, L. Ramezani, Mol. Catal. 435, 166 (2017)Google Scholar
  19. 19.
    A. Bamoniri, N. Moshtael-Arani, RSC Adv. 5, 16911 (2015)Google Scholar
  20. 20.
    N. Azgomi, M. Mokhtar, J. Mol. Catal. A Chem. 398, 58 (2015)Google Scholar
  21. 21.
    M.A. Bodaghifard, S. Asadbegi, Z. Bahrami, J. Iran. Chem. 14, 365 (2017)Google Scholar
  22. 22.
    M.A. Zolfigol, M. Safaiee, N. Bahrami-Nejad, New J. Chem. 40, 5071 (2016)Google Scholar
  23. 23.
    F. Javaheri, S. Hassanajili, J. Appl. Polym. Sci. 133, 48 (2016)Google Scholar
  24. 24.
    A. Ghorbani-Choghamarani, G. Azadi, Appl. Organomet. Chem. 30, 247 (2016)Google Scholar
  25. 25.
    M.A. Zolfigol, M. Kiafar, M. Yarie, A.A. Taherpour, M. Saeidi-Rad, RSC Adv. 6, 50100 (2016)Google Scholar
  26. 26.
    Q. Dai, Y. Wang, W. Xu, Y. Liu, Y. Zhou, Mikrochim. Acta 184, 4433 (2017)Google Scholar
  27. 27.
    S.A. Hamrahian, J. Rakhtshah, S.M. Mousavi Davijani, S. Salehzadeh, Appl. Organomet. Chem. 10, e4501 (2018)Google Scholar
  28. 28.
    H.A. Patel, A.M. Sawant, V.J. Rao, A.L. Patel, A.V. Bedekar, Catal. Lett. 147, 2306 (2017)Google Scholar
  29. 29.
    D. Sahu, A.R. Silva, P. Das, RSC Adv. 5, 78553 (2015)Google Scholar
  30. 30.
    H. Singh, J.K. Rajput, G. Govil, P. Arora, J. Badhan, Appl. Organomet. Chem. 10, e4514 (2018)Google Scholar
  31. 31.
    M. Esmaeilpour, A.R. Sardarian, H. Firouzabadi, Appl. Organomet. Chem. 32, e4300 (2018)Google Scholar
  32. 32.
    A. Burak, P. Handan, K. Muharrem, S. Fatih, J. Nanosci. Nanotechnol. 16, 6498 (2016)Google Scholar
  33. 33.
    R. Ulus, Y. Yıldız, S. Eriş, B. Aday, F. Şen, ChemistrySelect 1, 3861 (2016)Google Scholar
  34. 34.
    X. Liu, Z. Ma, J. Xing, H. Liu, J. Magn. Magn. Mater. 270, 1 (2004)Google Scholar
  35. 35.
    V.R. Mudumala, R.R. Chinthaparthi, T. Yeon, Tetrahedron 70, 3762 (2014)Google Scholar
  36. 36.
    Z. Zarei, B. Akhlaghinia, New J. Chem. 41, 15485 (2017)Google Scholar
  37. 37.
    B. Aday, Y. Yıldız, R. Ulus, S. Eris, F. Sen, M. Kaya, New J. Chem. 40, 748 (2016)Google Scholar
  38. 38.
    H.R. Safaei, M. Safaei, M. Shekouhy, RSC Adv. 5, 6797 (2015)Google Scholar
  39. 39.
    A. Maleki, T. Kari, M. Aghaei, J. Porous Mater. 24, 1481 (2017)Google Scholar
  40. 40.
    X. Zhu, S.-R. Kang, L. Xia, J. Lee, N. Basavegowda, Y.-R. Lee, Mol. Divers. 19, 67 (2015)PubMedGoogle Scholar
  41. 41.
    K. Venkatesan, S.S. Pujari, K.V. Srinivasan, Synth. Commun. 39, 228 (2009)Google Scholar
  42. 42.
    B. Das, P. Thirupathi, I. Mahender, V. Saidi Reddy, Y.K. Rao, J. Mol. Catal. A Chem. 247, 233 (2006)Google Scholar
  43. 43.
    M. Dabiri, M. Baghbanzadeh, E. Arzroomchilar, Catal. Commun. 9, 939 (2008)Google Scholar
  44. 44.
    K. Niknam, F. Panahi, D. Saberi, M. Mohagheghnejad, J. Heterocycl. Chem. 47, 292 (2010)Google Scholar
  45. 45.
    M.M. Alam, A.T. Mubarak, M.A. Assiri, S.M. Ahmed, BMC Chem. 13, 40 (2019)PubMedGoogle Scholar

Copyright information

© Springer Nature B.V. 2019

Authors and Affiliations

  1. 1.Department of Chemistry, Faculty of SciencesUniversity of Sistan and BaluchestanZahedanIran

Personalised recommendations