Skip to main content
Log in

Zn salen complex supported on MnCoFe2O4(MCF) magnetic nanoparticles as a catalyst in the synthesis of 3,4-dihydropyrimidin-2 (1H)-ones/thiones (Biginelli-like reaction)

  • Published:
Research on Chemical Intermediates Aims and scope Submit manuscript

Abstract

In the present work, a novel Zn salen complex supported on MnCoFe2O4 magnetic nanoparticles, MnCoFe2O4@SiO2-Pr-NH-SA&Zn (MCF@SiO2-Pr-NH-SA&Zn) was easily synthesized by a clean method and fully characterized by Fourier-transform infrared spectroscopy (FT-IR), X-ray diffraction, Field emission-scanning electron microscopy, Energy dispersive X-ray analyzer, Transmission electron microscopy, Inductively coupled plasma-optical emission spectrometry, Thermogravimetric and Vibrating sample magnetometery analyses. Moreover, the activity of the prepared complex as a heterogeneous catalyst was investigated in Biginelli-like reaction via three component reaction ethyl acetoacetate or dimedone/ or barbituric acid, urea/ or thiourea and different aromatic aldehydes. The structure of new prepared 3,4-dihydropyrimidin-2 (1H)-ones/thions was properly identified by FT-IR, 1H- and 13C-NMR spectroscopy data. Some important advantages of this procedure include easy separation of catalyst by a magnet, short reaction times, excellent yield of products, solvent free, easy work-up and reusability of the catalyst during 6 runs of the used model reaction.

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
Scheme 2
Fig. 6
Fig. 7
Fig. 8
Scheme 3

Similar content being viewed by others

References

  1. H.A. Younus, M. Al-Rashida, A. Hameed, M. Uroos, U. Salar, S. Rana et al., Expert Opin. Ther. Pat. 31, 267 (2021)

    Article  CAS  PubMed  Google Scholar 

  2. M.A. Ghasemzadeh, B. Mirhosseini-Eshkevari, M. Tavakoli, F. Zamani, Green Chem. 22, 7265 (2020)

    Article  CAS  Google Scholar 

  3. X. Ma, S. Zhi, W. Zhang, Molecules 26, 1986 (2021)

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  4. K.N. Singh, Org. Biomol. Chem. 19, 2622 (2021)

    Article  Google Scholar 

  5. F.G. Calvo-Flores, C. Mingorance-Sánchez, Chem. Open 10, 815 (2021)

    CAS  Google Scholar 

  6. H. Nagarajaiah, A. Mukhopadhyay, J.N. Moorthy, Tetrahedron Lett. 57, 5135 (2016)

    Article  CAS  Google Scholar 

  7. L.V. Chopda, P.N. Dave, Chem. Sel. 5, 5552 (2020)

    CAS  Google Scholar 

  8. Y.U. Gadkari, N.T. Hatvate, B.S. Takale, V.N. Telvekar, New. J. Chem. 44, 8167 (2020)

    Article  CAS  Google Scholar 

  9. I.V. Machado, J.R. Dos Santos, M.A. Januario, A.G. Corrêa, Ultrason Sonochem. 78, 105704 (2021)

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  10. P. Costanzo, M. Nardi, M. Oliverio, Eur. J. Org. Chem. 2020, 3954 (2020)

    Article  CAS  Google Scholar 

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

    Article  CAS  PubMed  Google Scholar 

  12. N. George, A.A. Manakkadan, A. Ariyath, S. Maniyamma, V. Vijayakumar, R.G. Pai et al., Curr. Drug Discov. Technol. 16, 127 (2019)

    Article  CAS  PubMed  Google Scholar 

  13. A. El-Malah, Z. Mahmoud, H. Hamed Salem, A.M. Abdou, M.M. Soliman, R.A. Hassan, Green Chem. Lett. Rev. 14, 220 (2021)

    Article  CAS  Google Scholar 

  14. A.E. Huseynzada, C. Jelch, H.V.N. Akhundzada, S. Soudani, C.B. Nasr, A. Israyilova et al., RSC Adv. 11, 6312 (2021)

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  15. J. Dong, M. Liu, R. Jiang, H. Huang, Q. Wan, Y. Wen et al., J. Colloid Interface Sci. 528, 192 (2018)

    Article  CAS  PubMed  Google Scholar 

  16. L. Rong, M. Zeng, H. Liu, B. Wang, Z. Mao, H. Xu et al., Carbohydr. Polym. 209, 223 (2019)

    Article  CAS  PubMed  Google Scholar 

  17. E. Khalili, N. Ahadi, M.A. Bodaghifard, J. Org. Chem. Res. 6, 272 (2020)

    Google Scholar 

  18. A. Mobinikhaledi, N. Foroughifar, H. Moghanian, H.R. Jaberi, J. Org. Chem. Res. 4, 95 (2018)

    Google Scholar 

  19. A. Mobinikhaledi, N. Foroughifar, A. Khajeh-Amiri, React. Kinet. Mech. Catal. 117, 59 (2016)

    Article  CAS  Google Scholar 

  20. S. Kargar, D. Elhamifar, A. Zarnegaryan, J. Phys. Chem. Solids. 146, 109601 (2020)

    Article  CAS  Google Scholar 

  21. A. Khazaei, F. Gohari-Ghalil, M. Tavasoli, M. Rezaei-Gohar, A.R. Moosavi-Zare, Chem. Methodol. 4, 543 (2020)

    CAS  Google Scholar 

  22. H. Moghanian, M.A.B. Fard, A. Mobinikhaledi, N. Ahadi, Res. Chem. Intermed. 44, 4083 (2018)

    Article  CAS  Google Scholar 

  23. A. Bamoniri, B.B.F. Mirjalili, M. MahmoodiFardChegeni, J. Nanostruct. 10, 751 (2020)

    CAS  Google Scholar 

  24. G. Padmapriya, A. Manikandan, V. Krishnasamy, S.K. Jaganathan, S.A. Antony, J. Supercond. Nov. Magn. 29, 2141 (2016)

    Article  CAS  Google Scholar 

  25. G. Datt, A. Abhyankar, J. Appl. Phys. 122, 034102 (2017)

    Article  CAS  Google Scholar 

  26. K. Dai, G. Liu, W. Xu, Z. Deng, Y. Wu, C. Zhao et al., J. Colloid Interface. Sci. 579, 815 (2020)

    Article  CAS  PubMed  Google Scholar 

  27. S.F. Taheri Hatkehlouei, B. Mirza, S. Soleimani-Amiri, Polycycl. Aromat. Comp. 3, 100169 (2020)

    Google Scholar 

  28. N. Ahadi, A. Mobinikhaledi, M.A. Bodaghifard, Appl. Organomet. Chem. 34, e5822 (2020)

    Article  CAS  Google Scholar 

  29. M.A. Bodaghifard, M. Hamidinasab, N. Ahadi, Curr. Org. Chem. 22, 234 (2018)

    Article  CAS  Google Scholar 

  30. A. Mobinikhaledi, N. Foroughifar, H.F. Jirandehi, Phosphorus Sulfur. 179, 2259 (2004)

    Article  CAS  Google Scholar 

  31. A. Mobinikhaledi, B. Asghari, M. Jabbarpour, Iran. J. Pharm. Res. 14, 723 (2015)

    PubMed  PubMed Central  Google Scholar 

  32. N. Ahadi, M.A. Bodaghifard, A. Mobinikhaledi, Appl. Organomet. Chem. 33, e4738 (2019)

    Article  CAS  Google Scholar 

  33. R. Ghorbani-Vaghei, S. Alavinia, Z. Merati, V. Izadkhah, Appl. Organomet. Chem. 32, e4127 (2018)

    Article  CAS  Google Scholar 

  34. H. Moghanian, A. Mobinikhaledi, A. Blackman, E. Sarough-Farahani, RSC Adva. 4, 28176 (2014)

    Article  CAS  Google Scholar 

  35. F. Xue, Y. Dong, P. Hu, Y. Deng, Y. Wei, RSC Adva. 5, 73684 (2015)

    Article  CAS  Google Scholar 

  36. A. Rezaei, H. Khani, M. Masteri-Farahani, M.K. Rofouei, Anal. Methods 4, 4107 (2012)

    Article  CAS  Google Scholar 

  37. A. Strecker, Justus Liebigs Ann. Chem. 75, 27 (1850)

    Article  Google Scholar 

  38. A. Hantzsch, Justus Liebigs Ann. Chem. 215, 1 (1882)

    Article  Google Scholar 

  39. M. Chandel, B.K. Ghosh, D. Moitra, M.K. Patra, S.R. Vadera, N.N. Ghosh, J. Nanosci. Nanotechnol. 18, 2481 (2018)

    Article  CAS  PubMed  Google Scholar 

  40. P. Akbarzadeh, N. Koukabi, Res. Chem. Intermed. 46, 4955 (2020)

    Article  CAS  Google Scholar 

  41. A.P. Ilyn, A.S. Trifilenkov, D.I. Kovrigin, M.V. Yudin, A.V. Ivachtchenko, Heterocycl. Comm. 12, 107 (2006)

    Article  CAS  Google Scholar 

  42. J. Javidi, M. Esmaeilpour, F.N. Dodeji, RSC Adva. 5, 308 (2015)

    Article  CAS  Google Scholar 

  43. C.O. Kappe, J. Org. Chem. 62, 7201 (1997)

    Article  CAS  PubMed  Google Scholar 

  44. J.S. Sandhu, ARKIVOC 68, 66 (2012)

    Google Scholar 

  45. J. Azizian, M.K. Mohammadi, O. Firuzi, B. Mirza, R. Miri, Chem. Biol. Drug. Des. 75, 375 (2010)

    Article  CAS  PubMed  Google Scholar 

  46. A. Mobinikhaledi, N. Foroughifar, A. Ghorbani, Phosphorus Sulfur 180, 1713 (2005)

    Article  CAS  Google Scholar 

  47. M. Kidwai, S. Saxena, M.K.R. Khan, S. Thukral, Eur. J. Med. Chem. 40, 816 (2005)

    Article  CAS  PubMed  Google Scholar 

  48. Z. Hassani, M.R. Islami, M. Kalantari, Bioorg. Med. Chem. Lett. 16, 4479 (2006)

    Article  CAS  PubMed  Google Scholar 

  49. Z.N. Siddiqui, T. Khan, RSC Adva. 4, 2526 (2014)

    Article  CAS  Google Scholar 

  50. M.A. Mohamed, N. Mahmoud, A. El-Saghier, Chem. J. 2, 64 (2012)

    CAS  Google Scholar 

  51. R. Tayebee, M.M. Amini, M. Ghadamgahi, M. Armaghan, J. Mol. Catal. A Chem. 366, 266 (2013)

    Article  CAS  Google Scholar 

  52. H. Alinezhad, K. Pakzad, Org. Prep. Proced. Int. 52, 319 (2020)

    Article  CAS  Google Scholar 

  53. A. Allahresani, M.M. Sangani, M.A. Nasseri, K. Hemmat, Inorg. Chem. Commun. 118, 107988 (2020)

    Article  CAS  Google Scholar 

  54. U. Patel, B. Parmar, P. Patel, A. Dadhania, E. Suresh, Mater. Chem. Front. 5, 304 (2021)

    Article  CAS  Google Scholar 

  55. N.S. Nandurkar, M.J. Bhanushali, M.D. Bhor, B.M. Bhanage, J. Mol. Catal. A Chem. 271, 14 (2007)

    Article  CAS  Google Scholar 

  56. M.A. KarimiZarchi, Z. Hamidi, React. Kinet. Mech. Catal. 125, 1023 (2018)

    Article  CAS  Google Scholar 

  57. L.M. Ramos, A.Y. de Ponce Leon y Tobio, M.R. dos Santos, H.C. de Oliveira, A.F. Gomes, F.C. Gozzo et al., J. Org. Chem. 77, 10184 (2012)

    Article  CAS  PubMed  Google Scholar 

Download references

Acknowledgements

We gratefully acknowledge the financial support of this work by the research council of Arak University.

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to Akbar Mobinikhaledi.

Additional information

Publisher's Note

Springer Nature remains neutral with regard to jurisdictional claims in published maps and institutional affiliations.

Supplementary Information

Below is the link to the electronic supplementary material.

Supplementary file1 (DOCX 4866 kb)

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Ahadi, N., Mobinikhaledi, A., Fathehesami, A. et al. Zn salen complex supported on MnCoFe2O4(MCF) magnetic nanoparticles as a catalyst in the synthesis of 3,4-dihydropyrimidin-2 (1H)-ones/thiones (Biginelli-like reaction). Res Chem Intermed 48, 2469–2488 (2022). https://doi.org/10.1007/s11164-022-04709-6

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11164-022-04709-6

Keywords

Navigation