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Preparation and characterization of Fe3O4@Cu-β-CD as a hybrid magnetic catalyst for the synthesis of dihydropyrano[2,3-c]pyrazoles in H2O

  • Fatemeh Mirhashemi
  • Mohammad Ali AmrollahiEmail author
Article
  • 8 Downloads

Abstract

Fe3O4@Cu-β-CD is a hybrid composite with high catalytic activity. Easy separation with an external magnet and recyclability are the advantages of this catalyst. The magnetic composite was characterized by TEM, FE-SEM, XRD, EDS, VSM and FT-IR techniques. The result of the TEM analysis shows that the average size of the Fe3O4@Cu-β-CD composite is less than 80 nm. The catalyst was applied for the synthesis of dihydropyrano[2,3-c]pyrazole derivatives in water. Various dihydropyrano[2,3-c]pyrazole derivatives were prepared in high to excellent yields with short reaction times and high purity in aqueous medium.

Graphical abstract

Keywords

Hybrid composite β-CD Dihydropyrano[2,3-c]pyrazoles Fe3O4@Cu-β-CD Inclusion complex 

Notes

Acknowledgements

The authors thank the Research Council of Yazd University for the financial support.

References

  1. 1.
    A.S. Teja, P.Y. Koh, Prog. Cryst. Growth Charact. Mater. 55, 22 (2009)CrossRefGoogle Scholar
  2. 2.
    M. Godoi, D.G. Liz, E.W. Ricardo, M.S.T. Rocha, M.B. Azeredo, A.L. Braga, Tetrahedron 70, 3349 (2014)CrossRefGoogle Scholar
  3. 3.
    J. Kudr, Y. Haddad, L. Richtera, Z. Heger, M. Cernak, V. Adam, O. Zitka, Nanomaterials 7, 243 (2017)CrossRefGoogle Scholar
  4. 4.
    M. Haruta, N. Yamada, T. Kobayashi, S. Iijima, J. Catal. 115, 301 (1989)CrossRefGoogle Scholar
  5. 5.
    M.S. Chen, D.V. Goodman, Science 306, 252 (2004)CrossRefGoogle Scholar
  6. 6.
    H. Wang, T. You, W. Shi, J. Li, L. Guo, J. Phys. Chem. C 116, 6490 (2012)CrossRefGoogle Scholar
  7. 7.
    S. Chen, R. Si, E. Taylor, J. Janzen, J. Chen, J. Phys. Chem. C 116, 12969 (2012)CrossRefGoogle Scholar
  8. 8.
    M.O. Simon, C.J. Li, Chem. Soc. Rev. 41, 1415 (2012)CrossRefGoogle Scholar
  9. 9.
    A. Harada, Acc. Chem. Res. 34, 456 (2001)CrossRefGoogle Scholar
  10. 10.
    G. Chen, M. Jiang, Chem. Soc. Rev. 40, 2254 (2011)CrossRefGoogle Scholar
  11. 11.
    N. Aparecida Liberto, S. Paiva Silva, A. Fatima, S. Antonio Fernandes, Tetrahedron 69, 8245 (2013)CrossRefGoogle Scholar
  12. 12.
    Y. Ren, Y. Liu, R. Niu, X. Liao, J. Zhang, B. Yang, J. Mol. Struct. 1117, 1 (2016)CrossRefGoogle Scholar
  13. 13.
    S.V. Bhosale, S.V. Bhosale, Mini-Rev. Org. Chem. 4, 231 (2007)CrossRefGoogle Scholar
  14. 14.
    P. Tang, H. Yang, B. Tang, D. Wu, Q. Du, K. Xu, H. Li. Carbohydr. Polym. 156, 215 (2017)CrossRefGoogle Scholar
  15. 15.
    M. Komiyama, M.L. Bender, The Chemistry of Enzyme Action (Elsevier, Amsterdam, 1984), p. 505CrossRefGoogle Scholar
  16. 16.
    X. Chen, J. Rao, J. Wang, J.J. Gooding, G. Zou, Q. Zhang, Chem. Commun. 47, 10317 (2011)CrossRefGoogle Scholar
  17. 17.
    L. Kong, G. Fang, Y. Kong, M. Xie, V. Natarajan, D. Zhou, J. Zhan, J. Hazard. Mater. (2018).  https://doi.org/10.1016/j.jhazmat.2018.05.065
  18. 18.
    B. Kaboudin, Y. Abedi, T. Yokomatsu, Eur. J. Org. Chem. 33, 6656 (2011)CrossRefGoogle Scholar
  19. 19.
    B. Kaboudin, R. Mostafalua, T. Yokomatsu, Green Chem. 15, 2266 (2013)CrossRefGoogle Scholar
  20. 20.
    B. Kaboudin, H. Salemi, R. Mostafalu, F. Kazemi, T. Yokomatsu, J. Organomet. Chem. 818, 195 (2016)CrossRefGoogle Scholar
  21. 21.
    H. Salemi, B. Kaboudin, F. Kazemi, T. Yokomatsu, RSC Adv. 6, 52656 (2016)CrossRefGoogle Scholar
  22. 22.
    R. Venkatesham, S. Rao, K. Nagaiah, J. Yadav, G. RoopaJones, S. Basha, B. Sridhar, A. Addlagatta, Med. Chem. Commun. 3, 652 (2012)CrossRefGoogle Scholar
  23. 23.
    M. Rueping, E. Sugiono, E. Merino, Chem. Eur. J. 14, 6329 (2008)CrossRefGoogle Scholar
  24. 24.
    D.O. Moon, K.C. Kim, C.Y. Jin, M.H. Han, C. Park, K.J. Lee, Y.M. Park, Y.H. Choi, G.Y. Kim, Int. Immunopharmacol. 7, 222 (2007)CrossRefGoogle Scholar
  25. 25.
    V.F. de Andrade-Neto, M.L.O. Goulart, J.F. da Silva Filho, M.J. da Silva, F. Maria do Carmo, A.V. Pinto, M.G. Zalis, L.H. Carvalho, A.U. Krettli, Bioorg. Med. Chem. Lett. 14, 1145 (2004)CrossRefGoogle Scholar
  26. 26.
    Y.A. Tayade, S.A. Padvi, Y.B. Wagh, D.S. Dalal, Tetrahedron Lett. 56, 2141 (2015)CrossRefGoogle Scholar
  27. 27.
    M. Babaie, H. Sheibani, Arab. J. Chem. 4, 159 (2011)CrossRefGoogle Scholar
  28. 28.
    H.R. Shaterian, K. Azizi, Res. Chem. Intermed. 40, 661 (2014)CrossRefGoogle Scholar
  29. 29.
    KhG Patel, N.M. Misra, R.H. Vekariya, R.R. Shettigar, Res. Chem. Intermed. 44, 289 (2018)CrossRefGoogle Scholar
  30. 30.
    H. Mecadon, MdR Rohman, I. Kharbangar, B.M. Laloo, I. Kharkongor, M. Rajbangshi, B. Myrboh, Tetrahedron Lett. 52, 3228 (2011)CrossRefGoogle Scholar
  31. 31.
    M. Arghan, N. Koukabi, E. Kolvari, J. Saudi. Chem. Soc. (2018).  https://doi.org/10.1016/j.jscs
  32. 32.
    K. Can, M. Ozmen, M. Ersoz, Colloids Surf. B 71, 154 (2009)CrossRefGoogle Scholar

Copyright information

© Springer Nature B.V. 2019

Authors and Affiliations

  1. 1.Department of Chemistry, College of ScienceYazd UniversityYazdIran

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