Skip to main content
Log in

Silica-coated magnetic NiFe2O4 nanoparticles-supported H3PW12O40; synthesis, preparation, and application as an efficient, magnetic, green catalyst for one-pot synthesis of tetrahydrobenzo[b]pyran and pyrano[2,3-c]pyrazole derivatives

  • Published:
Research on Chemical Intermediates Aims and scope Submit manuscript

    We’re sorry, something doesn't seem to be working properly.

    Please try refreshing the page. If that doesn't work, please contact support so we can address the problem.

Abstract

A powerful, magnetic, supported, acid catalyst, NiFe2O4@SiO2–H3PW12O40, was prepared by chemical support of Keggin (H3PW12O40) heteropolyacid (HPA) on silica-coated NiFe2O4 magnetic nanoparticles. XRD, TEM, SEM, VSM, and FTIR confirmed that the keggin HPA is well dispersed on the surface of silica-coated NiFe2O4 magnetic nanoparticles. The magnetically recoverable catalyst could be easily recycled at least six times without significant loss of catalytic activity. After full characterization, its catalytic activity was investigated in the synthesis of tetrahydrobenzo[b]pyran and pyrano[2,3-c]pyrazole derivatives.

Graphical Abstract

(1) Novel silica-coated magnetic NiFe2O4 nanoparticles-supported H3PW12O40 was fabricated and characterized. (2) Recyclability of the catalyst. (3) Avoiding use of corrosive acid catalysts. (4) Green chemistry.

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
Fig. 3
Fig. 4
Fig. 5
Scheme 3
Scheme 4
Fig. 6
Scheme 5

Similar content being viewed by others

References

  1. D.R. Park, H. Kim, J.C. Jung, S.H. Lee, I.K. Song, Chem. Res. Intermed. 34, 845 (2008)

    Article  CAS  Google Scholar 

  2. A. Vafaee, A. Davoodnia, M. Pordel, Chem. Res. Intermed. (2015). doi:10.1007/s11164-014-1896-y

    Google Scholar 

  3. P.H. Li, B.L. Li, Z.M. An, L.P. Mo, Z.S. Cui, Z.H. Zhang, Adv. Synth. Catal. 355, 2952 (2013)

    Article  CAS  Google Scholar 

  4. E. Rafiee, M. Kahrizi, Chem. Res. Intermed. (2015). doi:10.1007/s11164-015-2077-3

    Google Scholar 

  5. H. Zhang, J. Han, F. Tian, Q. Chen, C. Wang, H. Jin, G. Bai, Chem. Res. Intermed. (2015). doi:10.1007/s11164-014-1772-9

    Google Scholar 

  6. E. Rafiee, M. Kahrizi, Chem. Res. Intermed. (2015). doi:10.1007/s11164-013-1392-9

    Google Scholar 

  7. H. Liu, J. Deng, J.W. Gao, Z.H. Zhang, Adv. Synth. Catal. 354, 441 (2012)

    Article  CAS  Google Scholar 

  8. F.P. Ma, P.H. Li, B.L. Li, L.P. Mo, N. Liu, H.J. Kang, Y.N. Liu, Z.H. Zhang, Appl. Catal. A Gen. 457, 34 (2013)

    Article  CAS  Google Scholar 

  9. J. Lu, X.T. Li, E.Q. Ma, L.P. Mo, Z.H. Zhang, Chem. Cat. Chem. 6, 2854 (2014)

    CAS  Google Scholar 

  10. J. Deng, L.P. Mo, F.Y. Zhao, L.L. Hou, L. Yang, Z.H. Zhang, Green Chem. 13, 2576 (2011)

    Article  CAS  Google Scholar 

  11. L.L. Andreani, E. Lapi, Bull. Chim. Farm. 99, 583 (1960)

    Google Scholar 

  12. L. Bonsignore, G. Loy, D. Secci, A. Calignano, Eur. J. Med. Chem. 28, 517–520 (1993)

    Article  CAS  Google Scholar 

  13. C.S. Konkoy, D.B. Fick, S.X. Cai, N.C. Lan, J.F.W. Keana, PCT Int. Appl. WO 75 123, 2000. Chem. Abstr. 134, 29313a (2001)

  14. S.J. Tu, Y. Gao, C. Guo, D. Shi, Z.A. Lu, Synth. Commun. 32, 2137 (2002)

    Article  CAS  Google Scholar 

  15. X.S. Wang, D.Q. Shi, S.J. Tu, C.H. Yao, Synth. Commun. 33, 119 (2003)

    Article  CAS  Google Scholar 

  16. S.J. Tu, X.H. Liu, H.J. Ma, D.Q. Shi, F. Liu, Chin. Chem. Lett. 13, 393 (2002)

    CAS  Google Scholar 

  17. L. Rong, Synth. Commun. 36, 2363 (2006)

    Article  CAS  Google Scholar 

  18. N.M.A. El-Rahman, A.A. El-Kateb, M.F. Mady, Synth. Commun. 37, 3961 (2007)

    Article  Google Scholar 

  19. S.B. Guo, S.X. Wang, J.T.D. Li, Synth. Commun. 37, 2111 (2007)

    Article  CAS  Google Scholar 

  20. J.M. Khurana, B. Nand, S. Kumar, Synth. Commun. 41, 405 (2011)

    Article  CAS  Google Scholar 

  21. J.F. Zhou, S.J. Tu, H.Q. Zhu, S.J. Zhi, Synth. Commun. 32, 3363 (2002)

    Article  CAS  Google Scholar 

  22. T.S. Jin, A.Q. Wang, X. Wang, J.S. Zhang, T.S. Li, Synlett 5, 871 (2004)

    Article  Google Scholar 

  23. I. Devi, P.J. Bhuyan, Tetrahedron Lett. 45, 8625 (2004)

    Article  CAS  Google Scholar 

  24. Y. Li, B. Du, X. Wang, D. Shi, S. Tu, J. Heterocycl. Chem. 43, 685 (2006)

    Article  CAS  Google Scholar 

  25. B.C. Ranu, S. Banerjee, S. Roy, Indian J. Chem. 47B, 1108 (2008)

    CAS  Google Scholar 

  26. L. Zhao, Y. Li, L. Chen, B. Zhou, Chin. J. Org. Chem. 30, 124 (2010)

    CAS  Google Scholar 

  27. D. Fang, H.B. Zhang, Z.L. Liu, J. Heterocycl. Chem. 47, 63 (2010)

    CAS  Google Scholar 

  28. H.R. Shaterian, M. Arman, F. Rigi, J. Mol. Liq. 158, 145 (2011)

    Article  CAS  Google Scholar 

  29. P.P. Salvi, A.M. Mandhare, A.S. Sartape, D.K. Pawar, S.H. Han, S.S. Kolekar, C. R. Chim. 14, 878 (2011)

    Article  CAS  Google Scholar 

  30. S. Balalaie, M. Sheikh-Ahmadi, M. Bararjanian, Catal. Commun. 8, 1724 (2007)

    Article  CAS  Google Scholar 

  31. S. Balalaie, M. Bararjanian, M. Sheikh-Ahmadi, Synth. Commun. 37, 1097 (2007)

    Article  CAS  Google Scholar 

  32. X.Z. Lian, Y. Huang, Y.Q. Li, W.J. Zheng, Monatsh. Chem. 139, 129 (2008)

    Article  CAS  Google Scholar 

  33. R. Hekmatshoar, S. Majedi, K. Bakhtiari, Catal. Commun. 9, 307 (2008)

    Article  CAS  Google Scholar 

  34. A. Mobinikhaledi, M.A. Bodaghifard, Acta Chim. Slov. 57, 931 (2010)

    CAS  Google Scholar 

  35. S. Gurumurthi, V. Sundari, R. Valliappan, E.-J. Chem. 6(S1), S466 (2009)

    Article  CAS  Google Scholar 

  36. A.A. Yelwande, B.R. Arbad, M.K. Lande, Afr. J. Chem. 63, 199 (2010)

    Google Scholar 

  37. A. Mobinikhaledi, N. Foroughifar, M.A. Bodaghifard, Synth. React. Inorg. Metal-Org. Nano-Matal. Chem. 40, 179 (2010)

    CAS  Google Scholar 

  38. I.M. Wang, J.H. Shao, H. Tian, Y.H. Wang, B. Liu, J. Fluor. Chem. 127, 97 (2006)

    Article  CAS  Google Scholar 

  39. H. Abdi-Oskooie, M.M. Heravi, N. Karimi, M. Ebrahimzadeh, Synth. Commun. 41, 436 (2011)

    Article  Google Scholar 

  40. L.Q. Yu, F. Liu, Q.D. You, Org. Prep. Proc. Int. 41, 77 (2009)

    Article  CAS  Google Scholar 

  41. D.M. Pore, K.A. Undale, B.B. Dongare, U.V. Desai, Catal. Lett. 132, 104 (2009)

    Article  CAS  Google Scholar 

  42. A. Davoodnia, S. Allameh, S. Fazli, N. Tavakoli–Hoseini, Chem. Pap. 65, 714 (2011)

    Article  CAS  Google Scholar 

  43. L. Chagjun, W. Jianqiang, Z. Guohua, W. Wei, T. Shingui, G. Cheng, Chin. J. Org. Chem. 31, 860 (2011)

    Google Scholar 

  44. M. Dutta, P. Saikia, S. Gogoi, R.C. Boruah, Steroids 78, 387 (2013)

    Article  CAS  Google Scholar 

  45. A. Khazaei, F. Gholami, V. Khakyzadeh, A.R. Moosavi-Zare, J. Afsar, RSC Adv. 5, 14305 (2015)

    Article  CAS  Google Scholar 

  46. B. Maleki, S. Sedigh Ashrafi, RSC Adv. 4, 42873 (2014)

    Article  CAS  Google Scholar 

  47. A. Keyume, Z. Esmayil, L. Wang, F. Jun, Tetrahedron 70, 3976 (2014)

    Article  CAS  Google Scholar 

  48. S. Sadjadi, M.M. Heravi, Tetrahedron 67, 2707 (2011)

    Article  CAS  Google Scholar 

  49. B. Jiang, L.Y. Xue, X.H. Wang, M.S. Tu, Y.P. Liu, S.J. Tu, Tetrahedron Lett. 53, 1261 (2012)

    Article  CAS  Google Scholar 

  50. W. Liju, K. Ablajan, F. Jun, Ultrason. Sonochem. 22, 113 (2014)

    Article  Google Scholar 

  51. F. Shahbazi, K. Amani, Catal. Commun. 55, 57 (2014)

    Article  CAS  Google Scholar 

  52. B. Maleki, M. Baghayeri, S.M. Vahdat, A. Mohammadzadeh, S. Akhoondi, RSC Adv. 4, 46545 (2015)

    Article  Google Scholar 

  53. B. Maleki, F. Taimazi, Org. Prep. Proc. Int. 46, 252 (2014)

    Article  CAS  Google Scholar 

  54. B. Maleki, E. Rezaee-Seresht, Z. Ebrahimi, Org. Prep. Proc. Int. 47, 149 (2015)

    Article  CAS  Google Scholar 

  55. B. Maleki, Org. Prep. Proc. Int. 47, 173 (2015)

    Article  CAS  Google Scholar 

  56. B. Maleki, S. Sedigh Ashrafi, R. Tayebee, RSC Adv. 4, 41521 (2014)

    Article  CAS  Google Scholar 

  57. B. Maleki, S.B.N. Chalaki, S. Sedigh Ashrafi, E. Rezaee Seresht, F. Moeinpour, A. Khojastehnezhad, R. Tayebee, Appl. Organomet. Chem. 29, 290 (2015)

    Article  CAS  Google Scholar 

  58. B. Maleki, S. Sheikh, Org. Prep. Proc. Int. (2015). doi:10.1080/00304948.2015.1066647

    Google Scholar 

  59. B. Maleki, S. Babaee, R. Tayebee, Appl. Organomet. Chem. 29, 408 (2015)

    Article  CAS  Google Scholar 

  60. H. Veisi, B. Maleki, M. Hamelian, S. Sedigh Ashrafi, RSC Adv. 5, 6365 (2015)

    Article  CAS  Google Scholar 

  61. B. Maleki, S. Sheikh, RSC Adv. 5, 42997 (2015)

    Article  CAS  Google Scholar 

  62. H. Eshghi, A. Khojastehnezhad, F. Moeinpour, S. Rezaeian, M. Bakavoli, M. Teymouri, A. Rostami, K. Haghbeen, Tetrahedron 71, 436 (2015)

    Article  CAS  Google Scholar 

  63. H. Eshghi, A. Khojastehnezhad, F. Moeinpour, M. Bakavoli, S.M. Seyadi, M. Abbasi, RSC Adv. 4, 39782 (2014)

    Article  CAS  Google Scholar 

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

    Article  CAS  Google Scholar 

  65. E. Rafiee, S. Eavani, J. Mol. Catal. A Chem. 373, 30 (2013)

    Article  CAS  Google Scholar 

  66. K. Ablajan, L.J. Wang, Z. Maimaiti, Y.T. Lu, Monatsh. Chem. 145, 491 (2014)

    Article  CAS  Google Scholar 

Download references

Acknowledgments

The author thanks the Research Council of Hakim Sabzevari University for partial support of this work.

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to Behrooz Maleki.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Maleki, B., Eshghi, H., Barghamadi, M. et al. Silica-coated magnetic NiFe2O4 nanoparticles-supported H3PW12O40; synthesis, preparation, and application as an efficient, magnetic, green catalyst for one-pot synthesis of tetrahydrobenzo[b]pyran and pyrano[2,3-c]pyrazole derivatives. Res Chem Intermed 42, 3071–3093 (2016). https://doi.org/10.1007/s11164-015-2198-8

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11164-015-2198-8

Keywords

Navigation