Skip to main content
Log in

Fe3O4@Si-MCM-41@EDTA@Ni: as a magnetically recyclable and efficient nano-catalyst in the one-pot clean production of 2‐aryl‐2,3‐dihydroquinazolin‐4(1H)‐ones

  • Published:
Journal of Porous Materials Aims and scope Submit manuscript

Abstract

Ni-EDTA modified nano-magnetite Fe3O4 with shell silica-MCM-41 (Fe3O4@Si-MCM-41@EDTA@Ni) was designed using a post-grafting process and utilized as an effective, novel, and magnetic heterogeneous recoverable nano-catalyst in the clean production of 2,3-dihydroquinazolin-4(1H)-ones through cyclo-condensation. The structure of nano-catalyst was analyzed by TEM, TGA, XRD, FT-IR, EDS, SEM, VSM, ICP-AES tools and hot filtration test. The heterogeneous nanostructured Fe3O4@Si-MCM-41@EDTA@Ni with the saturation magnetization values 15.2 emu g−1 indicated great recyclability and could be easily reutilized for seven successive times no considerable decrease in its catalytic efficiency and activity. The desirable result was obtained with 1.0 mmol of 2-aminobenzamide and aldehyde in the existence of Fe3O4@MCM-41@APTES@EDTA@Ni (5 mg) and EtOH (4 ml) as clean solvent at reflux. Also, various aldehydes could smoothly participate in the cyclo-condensation reaction and produce quinazoline compounds with good yields %76–95.

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
Fig. 7
Fig. 8
Fig. 9
Fig. 10
Fig. 11
Fig. 12

Similar content being viewed by others

References

  1. J. Dobson, Gene Ther. 13, 283 (2006)

    CAS  PubMed  Google Scholar 

  2. M.M. Yallapu, S.F. Othman, E.T. Curtis, B.K. Gupta, M. Jaggi, S.C. Chauhan, Biomaterials 32, 1890 (2011)

    CAS  PubMed  Google Scholar 

  3. T.A. Rocha-Santos, TrAC Trends Anal. Chem. 62, 28 (2014)

    CAS  Google Scholar 

  4. M. Shinkai, J. Biosci. Bioeng. 94, 606 (2002)

    CAS  PubMed  Google Scholar 

  5. C. Guibert, V. Dupuis, V. Peyre, J. Fresnais, J. Phys. Chem. C 119, 28148 (2015)

    CAS  Google Scholar 

  6. Y. Qiu, S. Tong, L. Zhang, Y. Sakurai, D.R. Myers, L. Hong, W.A. Lam, G. Bao, Nat. Commun. 8, 15594 (2017)

    CAS  PubMed  PubMed Central  Google Scholar 

  7. R.N. Baig, R.S. Varma, Green Chem. 14, 625 (2012)

    Google Scholar 

  8. S. Rostamnia, B. Zeynizadeh, E. Doustkhah, A. Baghban, Kh Ojaghi Aghbash, Catal. Commun. 68, 77 (2015)

    CAS  Google Scholar 

  9. S. Shylesh, V. Schünemann, W.R. Thiel, Angew. Chem. Int. Ed. 49, 3428 (2010)

    CAS  Google Scholar 

  10. N. Basavegowda, K. Mishra, Y.R. Lee, RSC Adv. 4, 61660 (2014)

    CAS  Google Scholar 

  11. E. Rafiee, S. Eavani, Green Chem. 13, 2116 (2011)

    CAS  Google Scholar 

  12. H. Sun, J. He, J. Wang, S.-Y. Zhang, C. Liu, T. Sritharan, S. Mhaisalkar, M.-Y. Han, D. Wang, H. Chen, J. Am. Chem. Soc. 135, 9099 (2013)

    CAS  PubMed  Google Scholar 

  13. F. Lan, H. Hu, W. Jiang, K. Liu, X. Zeng, Y. Wu, Z. Gu, Nanoscale 4, 2264 (2012)

    CAS  PubMed  Google Scholar 

  14. W. Xie, X. Zang, Food Chem. 194, 1283 (2016)

    CAS  PubMed  Google Scholar 

  15. S. Luo, G. Fan, M. Luo, J. Li, G. Song, J. CO2 Util. 14, 23 (2016)

    CAS  Google Scholar 

  16. G. Bayramoglu, V.C. Ozalp, M. Oztekin, M.Y. Arica, Talanta 200, 263 (2019)

    CAS  PubMed  Google Scholar 

  17. G. Bayramoglu, H.M. Kayili, M. Oztekin, B. Salih, M.Y. Arica, Talanta 206, 120218 (2020)

    CAS  PubMed  Google Scholar 

  18. T.A. Arica, E. Ayas, M.Y. Arica, Microporous Mesoporous Mater. 243, 164 (2017)

    CAS  Google Scholar 

  19. S. Huh, J.W. Wiench, J.-C. Yoo, M. Pruski, V.S.-Y. Lin, Chem. Mater. 15, 4247 (2003)

    CAS  Google Scholar 

  20. Y. Xia, Z. Yang, R. Mokaya, Chem. Mater. 18, 1141 (2006)

    CAS  Google Scholar 

  21. D.E. De Vos, M. Dams, B.F. Sels, P.A. Jacobs, Chem. Rev. 102, 3615 (2002)

    PubMed  Google Scholar 

  22. R. Anwander, Chem. Mater. 13, 4419 (2001)

    CAS  Google Scholar 

  23. M. Fadhli, I. Khedher, J.M. Fraile, J. Mol. Catal. A-Chem. 420, 282 (2016)

    CAS  Google Scholar 

  24. G. Bayramoglu, M.Y. Arica, Microporous Mesoporous Mater. 226, 117 (2016)

    CAS  Google Scholar 

  25. J. Huang, M. Ye, Y. Qu, L. Chu, R. Chen, Q. He, D. Xu, J. Colloid Interface Sci. 385, 137 (2012)

    CAS  PubMed  Google Scholar 

  26. J. Rämö, M. Sillanpää, M. Orama, V. Vickackaite, L. Niinistö, J. Pulp. Pap. Sci. 26, 125 (2000)

    Google Scholar 

  27. Y. Liu, R. Fu, Y. Sun, X. Zhou, S.A. Baig, X. Xu, Appl. Surf. Sci. 369, 267 (2016)

    CAS  Google Scholar 

  28. F. Farjadian, S. Ghasemi, R. Heidari, S. Mohammadi-Samani, Nanomed-Nanotechnol. 13, 745 (2017)

    CAS  Google Scholar 

  29. L. Pena, D. Valencia, T. Klimova, Appl. Catal. B: Environ. 147, 879 (2014)

    CAS  Google Scholar 

  30. J.F. Wolfe, T.L. Rathman, M.C. Sleevi, J.A. Campbell, T.D. Greenwood, J. Med. Chem. 33, 161 (1990)

    CAS  PubMed  Google Scholar 

  31. M.-J. Hour, L.-J. Huang, S.-C. Kuo, Y. Xia, K. Bastow, Y. Nakanishi, E. Hamel, K.-H. Lee, J. Med. Chem. 43, 4479 (2000)

    CAS  PubMed  Google Scholar 

  32. J.B. Jiang, D. Hesson, B. Dusak, D. Dexter, G. Kang, E. Hamel, J. Med. Chem. 33, 1721 (1990)

    CAS  PubMed  Google Scholar 

  33. Y. Takaya, H. Tasaka, T. Chiba, K. Uwai, M.-A. Tanitsu, H.-S. Kim, Y. Wataya, M. Miura, M. Takeshita, Y. Oshima, J. Med. Chem. 42, 3163 (1999)

    CAS  PubMed  Google Scholar 

  34. K.-I. Ozaki, Y. Yamada, T. Oine, T. Ishizuka, Y. Iwasawa, J. Med. Chem. 28, 568 (1985)

    CAS  PubMed  Google Scholar 

  35. Y.H. Na, S.H. Hong, J.H. Lee, W.-K. Park, D.-J. Baek, H.Y. Koh, Y.S. Cho, H. Choo, A.N. Pae, Bioorg. Med. Chem. 16, 2570 (2008)

    CAS  PubMed  Google Scholar 

  36. Y. Xia, Z.-Y. Yang, M.-J. Hour, S.-C. Kuo, P. Xia, K.F. Bastow, Y. Nakanishi, P. Nampoothiri, T. Hackl, E. Hamel, Bioorg. Med. Chem. Lett. 11, 1193 (2001)

    CAS  PubMed  Google Scholar 

  37. D.A. Erlanson, R.S. McDowell, T. O'Brien, J. Med. Chem. 47, 3463 (2004)

    CAS  PubMed  Google Scholar 

  38. R.P. Maskey, M. Shaaban, I. Grün-Wollny, H. Laatsch, J. Nat. Prod. 67, 1131 (2004)

    CAS  PubMed  Google Scholar 

  39. S.E. López, M.E. Rosales, N. Urdaneta, M.V. Godoy, J.E. Charris, J. Chem. Res. 2000, 258 (2000)

    Google Scholar 

  40. S. Rostamizadeh, A.M. Amani, G.H. Mahdavinia, H. Sepehrian, S. Ebrahimi, Synthesis 2010, 1356 (2010)

    Google Scholar 

  41. J. Safari, S. Gandomi-Ravandi, J. Mol. Catal. A 371, 135 (2013)

    CAS  Google Scholar 

  42. A. Rostami, B. Tahmasbi, H. Gholami, H. Taymorian, Chin. Chem. Lett. 24, 211 (2013)

    CAS  Google Scholar 

  43. P. Sivaguru, K. Parameswaran, M. Kiruthiga, P. Vadivel, A. Lalitha, J. Iran. Chem. Soc. 12, 95 (2015)

    CAS  Google Scholar 

  44. Z.-B. Xie, S.-G. Zhang, G.-F. Jiang, D.-Z. Sun, Z.-G. Le, Green Chem. Lett. Rev. 8, 95 (2015)

    Google Scholar 

  45. H. Batmani, N. Noroozi Pesyan, F. Havasi, Microporous Mesoporous Mater. 257, 27 (2018)

    CAS  Google Scholar 

  46. M. Aalinejad, N. Noroozi Pesyan, N. Heidari, H. Batmani, A. Danandeh Asl, Appl. Organomet. Chem. 33, e4878 (2019)

    Google Scholar 

  47. Kh. Ojaghi Aghbash, N. Noroozi Pesyan, H. Batmani, Appl. Organomet. Chem. 33, e5227 (2019)

    CAS  Google Scholar 

  48. W. Stöber, A. Fink, E. Bohn, J. Colloid Interface Sci. 26, 62 (1968)

    Google Scholar 

  49. T. Martin, A. Galarneau, D. Brunel, V. Izard, V. Hulea, A. Blanc, S. Abramson, F. Di Renzo, F. Fajula, Stud. Surf. Sci. Catal. 135, 4621 (2001)

    CAS  Google Scholar 

  50. M. Rajesh, J. Sen, M. Srujan, K. Mukherjee, B. Sreedhar, A. Chaudhuri, J. Am. Chem. Soc. 129, 11408 (2007)

    CAS  PubMed  Google Scholar 

  51. W.-J. Liu, F.-X. Zeng, H. Jiang, X.-S. Zhang, Chem. Eng. J. 170, 21 (2011)

    CAS  Google Scholar 

  52. S. Ghosh, A. Badruddoza, M. Uddin, K. Hidajat, J. Colloid Interface Sci. 354, 483 (2011)

    CAS  PubMed  Google Scholar 

  53. Y. Liu, W. Zhang, X. Li, X. Le, J. Ma, New J. Chem. 39, 6474 (2015)

    CAS  Google Scholar 

  54. K. Li, Z. Zeng, J. Xiong, L. Yan, H. Guo, S. Liu, Y. Dai, T. Chen, Colloids Surf. A 465, 113 (2015)

    CAS  Google Scholar 

  55. L. Paltrinieri, M. Wang, S. Sachdeva, N.A. Besseling, E.J. Sudhölter, L.C. De Smet, J. Mater. Chem. A 5, 18476 (2017)

    CAS  Google Scholar 

  56. E. Repo, J.K. Warchol, T.A. Kurniawan, M.E. Sillanpää, Chem. Eng. J. 161, 73 (2010)

    CAS  Google Scholar 

  57. S. Hou, S. Su, M.L. Kasner, P. Shah, K. Patel, C.J. Madarang, Chem. Phys. Lett. 501, 68 (2010)

    CAS  Google Scholar 

  58. A.A. Romero, M.D. Alba, J. Klinowski, J. Phys. Chem. B 102, 123 (1998)

    CAS  Google Scholar 

  59. C.G. Netto, H.E. Toma, L.H. Andrade, J. Mol. Catal. B 85, 71 (2013)

    Google Scholar 

  60. B. Murugan, L.N. Ramana, S. Gandhi, S. Sethuraman, U.M. Krishnan, J. Mater. Chem. B 1, 3494 (2013)

    CAS  PubMed  Google Scholar 

  61. N. Wang, N. Gao, S. Jiang, Q. Fang, E. Chen, Compos. B 42, 1571 (2011)

    Google Scholar 

  62. M. Badolato, F. Aiello, N. Neamati, RSC Adv. 8, 20894 (2018)

    CAS  Google Scholar 

  63. H.R. Shaterian, A.R. Oveisi, Chin. J. Chem. Phys. 27, 2418 (2009)

    CAS  Google Scholar 

  64. M. Nikoorazm, A. Ghorbani-Choghamarani, M. Khanmoradi, RSC Adv. 6, 56549 (2016)

    CAS  Google Scholar 

  65. A. Davoodnia, S. Allameh, A. Fakhari, N. Tavakoli-Hoseini, Chin. Chem. Lett. 21, 550 (2010)

    CAS  Google Scholar 

  66. Q.S. Ding, J.L. Zhang, J.X. Chen, M.C. Liu, J.C. Ding, H.Y. Wu, J. Heterocycl. Chem. 49, 375 (2012)

    CAS  Google Scholar 

  67. M. Sharma, S. Pandey, K. Chauhan, D. Sharma, B. Kumar, P.M. Chauhan, J. Org. Chem. 77, 929 (2012)

    CAS  PubMed  Google Scholar 

  68. A. Rostami, A. Tavakoli, Chin. Chem. Lett. 22, 1317 (2011)

    CAS  Google Scholar 

  69. R.Z. Qiao, B.L. Xu, Y.H. Wang, Chin. Chem. Lett. 18, 656 (2007)

    CAS  Google Scholar 

  70. J.X. Chen, H.Y. Wu, W.K. Su, Chin. Chem. Lett. 18, 536 (2007)

    CAS  Google Scholar 

Download references

Acknowledgements

We thank a lot the Urmia University Research Council for supporting this work.

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to Nader Noroozi Pesyan.

Additional information

Publisher's Note

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

Electronic supplementary material

Below is the link to the electronic supplementary material.

Supplementary file1 (PDF 995 kb)

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Ojaghi Aghbash, K., Noroozi Pesyan, N. Fe3O4@Si-MCM-41@EDTA@Ni: as a magnetically recyclable and efficient nano-catalyst in the one-pot clean production of 2‐aryl‐2,3‐dihydroquinazolin‐4(1H)‐ones. J Porous Mater 27, 1087–1100 (2020). https://doi.org/10.1007/s10934-020-00882-4

Download citation

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10934-020-00882-4

Keywords

Navigation