Advertisement

Design and development of a new functionalized cellulose-based magnetic nanocomposite: preparation, characterization, and catalytic application in the synthesis of diverse pyrano[2,3-c]pyrazole derivatives

  • Ali MalekiEmail author
  • Vahid Eskandarpour
Original Paper
  • 9 Downloads

Abstract

In this work, a facile protocol for the preparation of a new cellulose-based functionalized magnetic nanocomposite catalyst is described. The structure and morphology of the prepared nanomaterial was characterized by scanning electron microscopy, energy-dispersive X-ray analysis, X-ray diffraction patterns, and Fourier transform infrared spectroscopy analyses. Then, its catalytic activity was investigated in the synthesis of 2,4-dihydropyrano[2,3-c]pyrazole and spiro[indoline-3,4′-pyrano[2,3-c]pyrazole derivatives through a one-pot four-component reaction between isatin or aldehydes or acetophenones, ethylacetoacetate, hydrazine hydrate, and malononitrile or ethylcyanoacetate in short reaction times, high yields, and mild conditions. The nanocomposite was simply separated by an external magnet and reused several times without remarkable loss of activity.

Keywords

Cellulose composite Magnetic bionanostructure Heterogeneous nanocatalyst Spiroindoline Pyranopyrazoles 

Notes

Acknowledgements

The authors gratefully acknowledge partial support from the Research Council of the Iran University of Science and Technology.

References

  1. 1.
    A. Maleki, Ultrason. Sonochem. 40, 460 (2018)CrossRefGoogle Scholar
  2. 2.
    A. Maleki, Tetrahedron 68, 7827 (2012)CrossRefGoogle Scholar
  3. 3.
    A. Maleki, R. Firouzi-Haji, Z. Hajizadeh, Int. J. Biol. Macromol. 116, 320 (2018)CrossRefGoogle Scholar
  4. 4.
    H.M. Al-Matar, K.D. Khalil, A.Y. Adam, M.H. Elnagdi, Molecules 15, 6619 (2010)CrossRefGoogle Scholar
  5. 5.
    Z.H. Ismail, G.M. Aly, M.S. El-Degwi, H.I. Heiba, M.M. Ghorab, Egypt. J. Biotechnol. 13, 73 (2003)Google Scholar
  6. 6.
    M.E. Zaki, H.A. Soliman, O.A. Hiekal, A.E. Rashad, Z. Naturforsch. C. 61, 1 (2006)CrossRefGoogle Scholar
  7. 7.
    R. Moosavi-Zare, M.A. Zolfigol, E. Noroozizadeh, M. Tavasoli, V. Khakyzadeh, A. Zare, New J. Chem. 37, 4089 (2013)CrossRefGoogle Scholar
  8. 8.
    A. Maleki, A.A. Jafari, S. Yousefi, Carbohydr. Polym. 175, 409 (2017)CrossRefGoogle Scholar
  9. 9.
    A. Maleki, M. Ghassemi, R. Firouzi Haji, Pure Appl. Chem. 90, 387 (2018)CrossRefGoogle Scholar
  10. 10.
    A. Maleki, R. Ghalavand, R. Firouzi-Haji, Iran. J. Catal. 8, 221 (2018)Google Scholar
  11. 11.
    A. Maleki, Polycycl. Aromat. Compd. 38, 402 (2018)CrossRefGoogle Scholar
  12. 12.
    G.S. Kumar, C. Kurumurthy, B. Veeraswamy, P.S. Rao, P.S. Rao, B. Narsaiah, Org. Prep. Proced. Int. 45, 429 (2013)CrossRefGoogle Scholar
  13. 13.
    J. Ebrahimi, A. Mohammadi, V. Pakjoo, E. Bahramzade, A. Habibi, J. Chem. Sci. 124, 1013 (2012)CrossRefGoogle Scholar
  14. 14.
    H. Mecadon, M.R. Rohman, M. Rajbangshi, B. Myrboh, Tetrahedron Lett. 52, 2523 (2011)CrossRefGoogle Scholar
  15. 15.
    R.J. Sundberg, Indoles. (Academic Press, New York, 1996)Google Scholar
  16. 16.
    J.F. Da Silva, S.J. Garden, A.C. Pinto, J. Braz. Chem. Soc. 12, 273 (2001)CrossRefGoogle Scholar
  17. 17.
    K.C. Joshi, P. Chand, Pharmazie 37, 1 (1982)Google Scholar
  18. 18.
    K.C. Joshi, R. Jain, K. Sharma, S.K. Bhattacharya, R.K. Goel, J. Indian Chem. Soc. 115, 202 (1988)Google Scholar
  19. 19.
    A.H. Abdel-Rahman, E.M. Keshk, M.A. Hanna, S.M. El-Bady, Bioorg. Med. Chem. 12, 2483 (2004)CrossRefGoogle Scholar
  20. 20.
    A. Maleki, Helv. Chim. Acta 97, 587 (2014)CrossRefGoogle Scholar
  21. 21.
    A. Maleki, Tetrahedron Lett. 54, 2055 (2013)CrossRefGoogle Scholar
  22. 22.
    A. Maleki, A.A. Jafari, S. Yousefi, V. Eskandarpour, C.R. Chim. 18, 1307 (2015)CrossRefGoogle Scholar
  23. 23.
    A. Maleki, V. Eskandarpour, J. Rahimi, N. Hamidi, Carbohydr. Polym. 208, 251 (2019)CrossRefGoogle Scholar
  24. 24.
    A. Maleki, A.A. Jafarim, S. Yousefi, J. Iran. Chem. Soc. 14, 1801 (2017)CrossRefGoogle Scholar
  25. 25.
    A. Maleki, M. Aghaei, R. Paydar, J. Iran. Chem. Soc. 14, 485 (2017)CrossRefGoogle Scholar
  26. 26.
    Z. Hajizadeh, A. Maleki, Mol. Catal. 460, 87 (2018)CrossRefGoogle Scholar
  27. 27.
    H.V. Chavan, S.B. Babar, R.U. Hoval, B.P. Bandgar, Bull. Korean Chem. Soc. 32, 3963 (2011)CrossRefGoogle Scholar
  28. 28.
    K. Kanagaraj, K. Pitchumani, Tetrahedron Lett. 51, 3312 (2010)CrossRefGoogle Scholar
  29. 29.
    S.N. Darandale, J.N. Sangshetti, D.B. Shinde, J. Korean Chem. Soc. 56, 328 (2012)CrossRefGoogle Scholar
  30. 30.
    M.A. Nasseri, S.M. Sadeghzadeh, Monatsh. Chem. 144, 151 (2013)CrossRefGoogle Scholar
  31. 31.
    K. Ablajan, W. Liju, A. Tuoheti, Y. Kelimu, Lett. Org. Chem. 9, 639 (2012)CrossRefGoogle Scholar
  32. 32.
    P.P. Bora, M. Bihani, G. Bez, J. Mol. Catal. B 92, 24 (2013)CrossRefGoogle Scholar
  33. 33.
    Y.M. Litvinov, A.A. Shestopalov, L.A. Rodinovskaya, A.M. Shestopalov, J. Comb. Chem. 11, 914 (2009)CrossRefGoogle Scholar
  34. 34.
    M. G.Dekamin,M.Alikhani,A.Emami,H.GhafuriandS.Javanshir,J. Iran. Chem. Soc., 2016,13,591.CrossRefGoogle Scholar
  35. 35.
    Y. Zou, Y. Hu, H. Liu, D. Shi, ACS Comb. Sci. 14, 38 (2011)CrossRefGoogle Scholar
  36. 36.
    R.G. Redkin, L.A. Shemchuk, V.P. Chernykh, O.V. Shishkin, S.V. Shishkina, Tetrahedron 63, 11444 (2007)CrossRefGoogle Scholar
  37. 37.
    R.Y. Guo, Z.M. An, L.P. Mo, S.T. Yang, H.X. Liu, S.X. Wang, Z.H. Zhang, Tetrahedron 69, 9931 (2013)CrossRefGoogle Scholar
  38. 38.
    J. Feng, K. Ablajan, A. Sali, Tetrahedron 70, 484 (2014)CrossRefGoogle Scholar
  39. 39.
    S. Ahadi, Z. Yasaei, A. Bazgir, Heterocycl. Chem. 47, 109 (2010)CrossRefGoogle Scholar
  40. 40.
    K. Ablajan, L.J. Wang, Z. Maimaiti, Y.T. Lu, Monatsh. Chem. 145, 491 (2014)CrossRefGoogle Scholar
  41. 41.
    H. Sachdeva, R. Saroj, Sci. World J., (2013).  https://doi.org/10.1155/2013/680671 Google Scholar

Copyright information

© Iranian Chemical Society 2019

Authors and Affiliations

  1. 1.Catalysts and Organic Synthesis Research Laboratory, Department of ChemistryIran University of Science and TechnologyTehranIran

Personalised recommendations