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

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.

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References

  1. 1.

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

    CAS  Article  Google Scholar 

  2. 2.

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

    Google Scholar 

  3. 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)

    CAS  Article  Google Scholar 

  4. 4.

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

    Google Scholar 

  5. 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. 6.

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

    Google Scholar 

  7. 7.

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

    CAS  Article  Google Scholar 

  8. 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)

    CAS  Article  Google Scholar 

  9. 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. 10.

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

    CAS  Article  Google Scholar 

  11. 11.

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

    Google Scholar 

  12. 12.

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

    CAS  Article  Google Scholar 

  13. 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. 14.

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

    CAS  Article  Google Scholar 

  15. 15.

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

    CAS  Article  Google Scholar 

  16. 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. 17.

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

    CAS  Article  Google Scholar 

  18. 18.

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

    Article  Google Scholar 

  19. 19.

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

    CAS  Article  Google Scholar 

  20. 20.

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

    CAS  Article  Google Scholar 

  21. 21.

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

    CAS  Article  Google Scholar 

  22. 22.

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

    Article  Google Scholar 

  23. 23.

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

    CAS  Article  Google Scholar 

  24. 24.

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

    CAS  Article  Google Scholar 

  25. 25.

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

    CAS  Google Scholar 

  26. 26.

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

    CAS  Google Scholar 

  27. 27.

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

    CAS  Google Scholar 

  28. 28.

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

    CAS  Article  Google Scholar 

  29. 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)

    CAS  Article  Google Scholar 

  30. 30.

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

    CAS  Article  Google Scholar 

  31. 31.

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

    CAS  Article  Google Scholar 

  32. 32.

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

    CAS  Article  Google Scholar 

  33. 33.

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

    CAS  Article  Google Scholar 

  34. 34.

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

    CAS  Google Scholar 

  35. 35.

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

    CAS  Article  Google Scholar 

  36. 36.

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

    Google Scholar 

  37. 37.

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

    CAS  Google Scholar 

  38. 38.

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

    CAS  Article  Google Scholar 

  39. 39.

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

    Article  Google Scholar 

  40. 40.

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

    CAS  Article  Google Scholar 

  41. 41.

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

    CAS  Article  Google Scholar 

  42. 42.

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

    CAS  Article  Google Scholar 

  43. 43.

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

    Google Scholar 

  44. 44.

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

    CAS  Article  Google Scholar 

  45. 45.

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

    CAS  Article  Google Scholar 

  46. 46.

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

    CAS  Article  Google Scholar 

  47. 47.

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

    CAS  Article  Google Scholar 

  48. 48.

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

    CAS  Article  Google Scholar 

  49. 49.

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

    CAS  Article  Google Scholar 

  50. 50.

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

    Article  Google Scholar 

  51. 51.

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

    CAS  Article  Google Scholar 

  52. 52.

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

    Article  Google Scholar 

  53. 53.

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

    CAS  Article  Google Scholar 

  54. 54.

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

    CAS  Article  Google Scholar 

  55. 55.

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

    CAS  Article  Google Scholar 

  56. 56.

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

    CAS  Article  Google Scholar 

  57. 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)

    CAS  Article  Google Scholar 

  58. 58.

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

    Google Scholar 

  59. 59.

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

    CAS  Article  Google Scholar 

  60. 60.

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

    CAS  Article  Google Scholar 

  61. 61.

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

    CAS  Article  Google Scholar 

  62. 62.

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

    CAS  Article  Google Scholar 

  63. 63.

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

    CAS  Article  Google Scholar 

  64. 64.

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

    CAS  Article  Google Scholar 

  65. 65.

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

    CAS  Article  Google Scholar 

  66. 66.

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

    CAS  Article  Google Scholar 

Download references

Acknowledgments

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

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Correspondence to Behrooz Maleki.

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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

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Keywords

  • Nanomagnetic catalyst
  • Heteropolyacid
  • Keggin
  • Tetrahydrobenzo[b]pyran
  • Pyrano[2,3-c]pyrazole