Skip to main content
Log in

MgFe2O4/cellulose/SO3H nanocomposite: a new biopolymer-based nanocatalyst for one-pot multicomponent syntheses of polysubstituted tetrahydropyridines and dihydropyrimidinones

  • Original Paper
  • Published:
Journal of the Iranian Chemical Society Aims and scope Submit manuscript

Abstract

A new biopolymer cellulose-based magnetic heterogeneous catalyst, MgFe2O4/cellulose/SO3H nanocomposite, was prepared. Fourier-transform infrared spectra, X-ray diffraction, energy-dispersive X-ray, field-emission scanning electron microscopy, thermal analysis (TG, DTG and DSC), dynamic light scattering and vibrating sample magnetometer measurements have been used to characterize the catalyst. Then, it was applied efficiently as an inexpensive and green catalyst in two multicomponent syntheses of polysubstituted tetrahydropyridines and dihydropyrimidinones under solvent-free conditions. The nanocatalyst can be recovered and reused several times without significant loss of catalytic activity.

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
Fig. 1
Fig. 2
Fig. 3
Fig. 4
Fig. 5
Fig. 6
Scheme 2
Scheme 3
Fig. 7

Similar content being viewed by others

References

  1. A. Maleki, Tetrahedron 68, 7827 (2012)

    Article  CAS  Google Scholar 

  2. A. Maleki, Tetrahedron Lett. 54, 2055 (2013)

    Article  CAS  Google Scholar 

  3. A. Maleki, S. Azadegan, Inorg. Nano-Met. Chem. 47, 917 (2017)

    Article  CAS  Google Scholar 

  4. A. Maleki, M. Aghaei, Ultrason. Sonochem. 38, 115 (2017)

    Article  CAS  Google Scholar 

  5. S. Maensiri, M. Sangmanee, A. Wiengmoon, Nanoscale Res. Lett. 4, 221 (2009)

    Article  CAS  Google Scholar 

  6. N.M. Deraz, Omar H. Abd-Elkader, Int. J. Electrochem. Sci. 8, 8632 (2013)

    CAS  Google Scholar 

  7. J. Lu, X. Wei, Y. Chang, S. Tian, Y. Xiong, J. Chem. Technol. Biotechnol. 91, 985 (2016)

    Article  CAS  Google Scholar 

  8. A. Maleki, R. Paydar, React. Funct. Polym. 109, 120 (2016)

    Article  CAS  Google Scholar 

  9. A. Maleki, H. Movahed, P. Ravaghi, Carbohydr. Polym. 156, 259 (2017)

    Article  CAS  Google Scholar 

  10. D. Klemm, B. Heublein, H.P. Fink, A. Bohn, Angew. Chem. Int. Ed. 44, 3358 (2005)

    Article  CAS  Google Scholar 

  11. F. Chen, M. Huang, Y. Li, Ind. Eng. Chem. Res. 53, 8339 (2014)

    Article  CAS  Google Scholar 

  12. A. Shaabani, A. Maleki, J. Moghimi-Rad, E. Soleimani, Chem. Pharm. Bull. 55, 957 (2007)

    Article  CAS  Google Scholar 

  13. A. Dömling, W. Wang, K. Wang, Chem. Rev. 112, 3083 (2012)

    Article  Google Scholar 

  14. T.J.J. Müller, in Science of Synthesis, Multicomponent, ed. by I. Reactions (T.J.J. Müller, Georg Thieme Verlag KG, Stuttgart, 2014), pp. 5–27

    Google Scholar 

  15. T. Gizur, B. Kiss, K.H. Bnyi, E. Karpati, E. Pglosi, A. Gere, E. Lapis, I. Laszlovszky, S. Szabo, L. Szporny, Eur. J. Med. Chem. 29, 349 (1994)

    Article  CAS  Google Scholar 

  16. S. Prachayasittikul, A. Worachartcheewan, R. Lawung, S. Ruchirawat, V. Prachayasittikul, EXCLI J. 8, 107 (2009)

    Google Scholar 

  17. R. Aeluri, M. Alla, V.R. Bommena, R. Murthy, N. Jain, Asian J. Org. Chem. 1, 71 (2012)

    Article  CAS  Google Scholar 

  18. W.S. Messer, Y.F. Abuh, Y. Liu, S. Periyasamy, D.O. Ngur, M.A.N. Edgar, A.A. El-Assadi, S. Sbeih, P.G. Dunbar, S. Roknich, T. Rho, Z. Fang, B. Ojo, H. Zhang, J.J. Huzl, P. Nagy, J. Med. Chem. 40, 1230 (1997)

    Article  CAS  Google Scholar 

  19. C.O. Kappe, Eur. J. Med. Chem. 35, 1043 (2000)

    Article  CAS  Google Scholar 

  20. A. Maleki, R. Rahimi, S. Maleki, Environ. Chem. Lett. 14, 195 (2016)

    Article  CAS  Google Scholar 

  21. A. Maleki, R. Rahimi, S. Maleki, J. Iran. Chem. Soc. 12, 191 (2015)

    Article  CAS  Google Scholar 

  22. A. Maleki, M. Aghaei, R. Paydar, J. Iran. Chem. Soc. 14, 485 (2017)

    Article  CAS  Google Scholar 

  23. A. Maleki, R. Paydar, RSC Adv. 5, 33177 (2015)

    Article  CAS  Google Scholar 

  24. A. Maleki, A.A. Jafari, S. Yousefi, V. Eskandarpour, C. R. Chim. 18, 1307 (2015)

    Article  CAS  Google Scholar 

  25. F. Tamaddon, Z. Razmi, A.A. Jafari, Tetrahedron Lett. 51, 1187 (2010)

    Article  CAS  Google Scholar 

  26. A. Shaabani, A. Maleki, Appl. Catal. A 331, 149 (2007)

    Article  CAS  Google Scholar 

  27. A. Shaabani, M. Seyyedhamzeh, A. Maleki, F. Rezazadeh, Appl. Catal. A 358, 146 (2009)

    Article  CAS  Google Scholar 

  28. A. Maleki, M. Kamalzare, Catal. Commun. 53, 67 (2014)

    Article  CAS  Google Scholar 

  29. A. Maleki, E. Akhlaghi, R. Paydar, Appl. Organomet. Chem. 30, 382 (2016)

    Article  CAS  Google Scholar 

  30. H.J. Wang, L.P. Mo, Z.H. Zang, ACS Comb. Sci. 13, 181 (2011)

    Article  CAS  Google Scholar 

  31. R. Ghorbani, H. Shahbazi, C. R. Chim. 16, 1047 (2013)

    Article  Google Scholar 

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

    Article  CAS  Google Scholar 

  33. U. Balijapalli, S. Munusamy, K.N. Sundaramoorthy, S.K. Iyer, Synth. Commun. 44, 943 (2014)

    Article  CAS  Google Scholar 

  34. R. Ramachandran, S. Jayanthi, Y.T. Jeong, Tetrahedron 68, 363 (2012)

    Article  CAS  Google Scholar 

  35. M. Kataria, S. Pramanik, M. Kumar, V. Bhalla, Chem. Commun. 51, 1483 (2015)

    Article  CAS  Google Scholar 

  36. J. Aboonajmi, M.R. Mousavi, M.T. Maghsoodlou, A. Masoumnia, N. Hazeri, Res. Chem. Intermed. 41, 1925 (2015)

    Article  CAS  Google Scholar 

  37. Q.J. Zhou, Y. Wan, X.X. Zhang, L. Zhang, H. Zou, S.L. Zhou, H.Y. Wang, H. Wu, H. Cui, Tetrahedron 71, 7070 (2015)

    Article  CAS  Google Scholar 

  38. N. Parikh, S. Roy, K. Seth, A. Kumar, A.K. Chakraborti, Synthesis 48, 547 (2016)

    CAS  Google Scholar 

  39. Y. Ma, C. Qian, L. Wang, M. Yang, J. Org. Chem. 65, 3864 (2000)

    Article  CAS  Google Scholar 

  40. J. Safari, S. Gandomi-Ravandi, J. Iran. Chem. Soc. 12, 147 (2015)

    Article  CAS  Google Scholar 

  41. H. Sharghi, M. Jokar, Synth. Commun. 39, 958 (2009)

    Article  CAS  Google Scholar 

  42. R. Fu, Y. Yang, W. Lai, Y. Ma, Zh Chen, J. Zhou, W. Cha, Q. Wang, R. Yuan, Synth. Commun. 45, 467 (2014)

    Article  Google Scholar 

Download references

Acknowledgements

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

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to Ali Maleki.

Ethics declarations

Conflict of interest

The authors declare that they have no conflict of interest.

Electronic supplementary material

Below is the link to the electronic supplementary material.

Supplementary material 1 (DOC 2063 kb)

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Maleki, A., Jafari, A.A. & Yousefi, S. MgFe2O4/cellulose/SO3H nanocomposite: a new biopolymer-based nanocatalyst for one-pot multicomponent syntheses of polysubstituted tetrahydropyridines and dihydropyrimidinones. J IRAN CHEM SOC 14, 1801–1813 (2017). https://doi.org/10.1007/s13738-017-1120-2

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s13738-017-1120-2

Keywords

Navigation