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Fabrication and characterization of the immobilized Cu(II) and Ni(II) species on silica-coated copper ferrite: as novel magnetically reusable nanocatalysts toward synthesis of biscoumarins

  • Behzad ZeynizadehEmail author
  • Maryam Sadeghbari
  • Nader Noroozi Pesyan
Original Paper
  • 2 Downloads

Abstract

In this study, we have synthesized magnetically nanoparticles (MNPs) of CuFe2O4@SiO2@AAPTMS@Ni(II) and CuFe2O4@SiO2@AAPTMS@Cu(II). The prepared nanocomposite systems were characterized using scanning electron microscopy, Fourier-transform infrared spectroscopy, X-ray diffraction, energy-dispersive X-ray spectroscopy, Brunauer–Emmett–Teller analysis, vibrating-sample magnetometer and inductively coupled plasma optical emission spectroscopy. Catalytic activity of CuFe2O4@SiO2@AAPTMS@Ni(II) and CuFe2O4@SiO2@AAPTMS@Cu(II) MNPs was also studied toward one-pot the Knoevenagel–Michael reaction of aromatic aldehydes with 4-hydroxycoumarin. All reactions were carried using 40 mg of the nanocatalysts in refluxing H2O within 12‒45 min to afford biscoumarin materials in 84–96% yield. The obtained results exhibited that catalytic activity of the Ni(II)-composite system was higher than the Cu(II)-analogue. Moreover, reusability of the nanocatalysts was examined for five consecutive cycles without the significant loss of the catalytic activity.

Keywords

Cu(II) CuFe2O4@SiO2 4-Hydroxycoumarin Knoevenagel–Michael Ni(II) 

Notes

Acknowledgements

The authors gratefully acknowledged the financial support of this work by the research council of Urmia University.

References

  1. 1.
    J. Kothandapani, S.S. Ganesan, Curr. Org. Chem. 23, 313 (2019)CrossRefGoogle Scholar
  2. 2.
    A. Bahuguna, A. Kumar, V. Krishnan, Asian J. Org. Chem. (2019).  https://doi.org/10.1002/ajoc.201900259 Google Scholar
  3. 3.
    V. Calvino-Casilda, A.J. López-Peinado, R.M. Martín-Aranda, E.P. Mayoral, Nanocatalysis: applications and technologies (CRC Press, Boca Raton, 2019)CrossRefGoogle Scholar
  4. 4.
    A.M. Abu-Dief, S.M. Abdel-Fatah, Beni-Suef Univ. J. Appl. Sci. 7, 55 (2018)Google Scholar
  5. 5.
    M. Van de Voorde, B. Sels, Nanotechnology in catalysis: applications in the chemical industry, energy development, and environment protection (Wiley-VCH, Weinheim, 2017)CrossRefGoogle Scholar
  6. 6.
    R.A. van Santen, Modern heterogeneous catalysis: an introduction (Wiley-VCH, Weinheim, 2017)CrossRefGoogle Scholar
  7. 7.
    M. Nasrollahzadeh, M. Atarod, M. Alizadeh, A. Hatamifard, S.M. Sajadi, Curr. Org. Chem. 21, 708 (2017)CrossRefGoogle Scholar
  8. 8.
    O. Mohammadi, M. Golestanzadeh, M. Abdouss, New J. Chem. 41, 11471 (2017)CrossRefGoogle Scholar
  9. 9.
    D. Wang, Astruc D. Chem. Rev. 114, 6949 (2014)CrossRefGoogle Scholar
  10. 10.
    J. Govan, Y.K. Gun’ko, Nanomaterials 4, 222 (2014)CrossRefGoogle Scholar
  11. 11.
    A. Stefanachi, F. Leonetti, L. Pisani, M. Catto, A. Carotti, Molecules 23, 250 (2018)CrossRefGoogle Scholar
  12. 12.
    F. Borges, F. Roleira, N. Milhazes, L. Santana, E. Uriarte, Curr. Med. Chem. 12, 887 (2005)CrossRefGoogle Scholar
  13. 13.
    S.M. Sethna, N.M. Shah, Chem. Rev. 36, 1 (1945)CrossRefGoogle Scholar
  14. 14.
    F.G. Medina, J.G. Marrero, M. Macias-Alonso, M.C. Gonzalez, I. Cordova-Guerrero, A.G. Teissier-Garcia, S. Osegueda-Roblesa, Nat. Prod. Rep. 32, 1472 (2015)CrossRefGoogle Scholar
  15. 15.
    J.C. Jung, O.S. Park, Molecules 14, 4790 (2009)CrossRefGoogle Scholar
  16. 16.
    I. Manolov, C. Maichle-Moessmer, N. Danchev, Eur. J. Med. Chem. 41, 882 (2006)CrossRefGoogle Scholar
  17. 17.
    C.X. Su, J.F. Mouscadet, C.C. Chiang, H.J. Tsai, L.Y. Hsu, Chem. Pharm. Bull. 54, 682 (2006)CrossRefGoogle Scholar
  18. 18.
    D. Yu, M. Suzuki, L. Xie, S.L. Morris-Natschke, K.H. Lee, Med. Res. Rev. 23, 322 (2003)CrossRefGoogle Scholar
  19. 19.
    H. Zhao, N. Neamati, H. Hong, A. Mazumder, S. Wang, S. Sunder, G.W.A. Milne, Y. Pommier, T.R. Burke, J. Med. Chem. 40, 242 (1997)CrossRefGoogle Scholar
  20. 20.
    J.C. Jung, J.H. Lee, S. Oh, J.G. Lee, O.S. Park, Bioorg. Med. Chem. Lett. 14, 5527 (2004)CrossRefGoogle Scholar
  21. 21.
    J. Li, X.Y. Xue, X. Li, Z. Hou, X.H. Yang, D. Qu, Y. Zhou, Z.D. Zhang, X.X. Luo, J.T. Li, Arch. Pharm. Res. 39, 1349 (2016)CrossRefGoogle Scholar
  22. 22.
    N. Hamdi, M.C. Puerta, P. Valerga, Eur. J. Med. Chem. 43, 2541 (2008)CrossRefGoogle Scholar
  23. 23.
    Z.H. Chohan, A.U. Shaikh, A. Rauf, C.T. Supuran, J. Enzyme Inhib. Med. Chem. 21, 741 (2006)CrossRefGoogle Scholar
  24. 24.
    I.J. Elenkov, B. Hrvacic, S. Markovic, M. Mesic, A.C. Klonkay, L. Lerman, A.F. Sucic, I. Vujasinovic, B. Bosnjak, K. Brajsa, D. Ziher, N.K. Hulita, I. Malnar, Croat. Chem. Acta 86, 253 (2013)CrossRefGoogle Scholar
  25. 25.
    I. Manolov, C. Maichle-Moessmer, I. Nicolova, N. Danchev, Arch. Pharm. 339, 319 (2006)CrossRefGoogle Scholar
  26. 26.
    M. Choudhary, N. Fatima, K.M. Khan, S. Jalil, S. Iqbal, A.U. Rahman, Bioorg. Med. Chem. 14, 8066 (2006)CrossRefGoogle Scholar
  27. 27.
    I. Kostova, G. Momekov, M. Zaharieva, M. Karaivanova, Eur. J. Med. Chem. 40, 542 (2005)CrossRefGoogle Scholar
  28. 28.
    V.D. Kancheva, V.P. Boranova, J. Nechev, I.I. Manolov, Biochimie 92, 1138 (2010)CrossRefGoogle Scholar
  29. 29.
    K.M. Khan, S. Iqbal, M.A. Lodhi, G.M. Maharvi, Z. Ullah, M.I. Choudhary, A.U. Rahman, S. Perveen, Bioorg. Med. Chem. 12, 1963 (2004)CrossRefGoogle Scholar
  30. 30.
    R.D.H. Murray, J. Mendez, S.A. Brown, The natural coumarins: occurrence, chemistry and biochemistry (Wiley, New York, 1982)Google Scholar
  31. 31.
    C.F. Heubner, W.R. Sullivan, M.A. Stahmann, K.P. Link, J. Am. Chem. Soc. 65, 2292 (1943)CrossRefGoogle Scholar
  32. 32.
    M. Kidwai, V. Bansal, P. Mothsra, S. Saxena, R.K. Somvanshi, S. Dey, T.P. Singh, J. Mol. Catal. A: Chem. 268, 76 (2007)CrossRefGoogle Scholar
  33. 33.
    V. Vahabi, F. Hatamjafari, Oriental J. Chem. 30, 853 (2014)CrossRefGoogle Scholar
  34. 34.
    Z.N. Siddiqui, F. Farooq, Catal. Sci. Technol. 1, 810 (2011)CrossRefGoogle Scholar
  35. 35.
    P. Singh, P. Kumar, A. Katyal, R. Kalra, S.K. Dass, S. Prakash, R. Chandra, Catal. Lett. 134, 303 (2010)CrossRefGoogle Scholar
  36. 36.
    J.M. Khurana, S. Kumar, Tetrahedron Lett. 50, 4125 (2009)CrossRefGoogle Scholar
  37. 37.
    B. Karmakar, A. Nayak, J. Banerji, Tetrahedron Lett. 53, 4343 (2012)CrossRefGoogle Scholar
  38. 38.
    F. Shirini, A. Fallah-Shojaei, L. Samavi, M. Abedini, RSC Adv. 6, 48469 (2016)CrossRefGoogle Scholar
  39. 39.
    B. Sadeghi, T. Ziya, J. Chem. 179013 (2013)Google Scholar
  40. 40.
    K. Niknam, A. Jamali, Chin. J. Catal. 33, 1840 (2012)CrossRefGoogle Scholar
  41. 41.
    M.M. Heravi, F. Nahavandi, S. Sadjadi, H.A. Oskooie, F.F. Bamoharram, Synth. Commun. 40, 498 (2010)CrossRefGoogle Scholar
  42. 42.
    V. Padalkar, K. Phatangare, S. Takale, R. Pisal, A. Chaskar, J. Saudi Chem. Soc. 19, 42 (2015)CrossRefGoogle Scholar
  43. 43.
    K. Kandasamy, M.P. Pachamuthu, M. Muthusamy, S. Ganesabaskaran, A. Ramanathan, RSC Adv. 3, 25367 (2013)CrossRefGoogle Scholar
  44. 44.
    H. Mehrabi, H. Abusaidi, J. Iran. Chem. Soc. 7, 890 (2010)CrossRefGoogle Scholar
  45. 45.
    B. Pawar, V. Shinde, A. Chaskar, Green Sustain. Chem. 3, 56 (2013)CrossRefGoogle Scholar
  46. 46.
    Z. Karimi-Jaberi, B. Masoudi, A. Rahmani, K. Alborzi, Polycycl. Aromat. Compd. (2017).  https://doi.org/10.1080/10406638.2017.1363061 Google Scholar
  47. 47.
    R. Rezaei, F. Moezzi, M.M. Doroodmand, Chin. Chem. Lett. 25, 183 (2014)CrossRefGoogle Scholar
  48. 48.
    F. Shirini, M. Mamaghani, M. Seddighi, Catal. Commun. 36, 31 (2013)CrossRefGoogle Scholar
  49. 49.
    M. Seddighi, F. Shirini, M. Mamaghani, RSC Adv. 3, 24046 (2013)CrossRefGoogle Scholar
  50. 50.
    S. Khodabakhshi, B. Karami, K. Eskandari, S.J. Hoseini, A. Rashidi, RSC Adv. 4, 17891 (2014)CrossRefGoogle Scholar
  51. 51.
    A. Nakhaei, S. Ramezani, Heterocycl. Lett. 7, 1035 (2017)Google Scholar
  52. 52.
    A. Tzani, A. Douka, A. Papadopoulos, E.A. Pavlatou, E. Voutsas, A. Detsi, ACS Sustain. Chem. Eng. 1, 1180 (2013)CrossRefGoogle Scholar
  53. 53.
    A. Zhu, M. Wang, L. Li, J. Wang, RSC Adv. 5, 73974 (2015)CrossRefGoogle Scholar
  54. 54.
    N. Tavakoli-Hoseini, M.M. Heravi, F.F. Bamoharram, A. Davoodnia, M. Ghassemzadeh, J. Mol. Liq. 163, 122 (2011)CrossRefGoogle Scholar
  55. 55.
    W. Li, Y. Wang, Z. Wang, L. Dai, Y. Wang, Catal. Lett. 141, 1651 (2011)CrossRefGoogle Scholar
  56. 56.
    B. Zeynizadeh, S. Rahmani, S. Ilkhanizadeh, Polyhedron 168, 48 (2019)CrossRefGoogle Scholar
  57. 57.
    B. Zeynizadeh, F. Sepehraddin, J. Organometal. Chem. 856, 70 (2018)CrossRefGoogle Scholar

Copyright information

© Iranian Chemical Society 2019

Authors and Affiliations

  1. 1.Department of Chemistry, Faculty of ScienceUrmia UniversityUrmiaIran

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