Skip to main content
SpringerLink
Log in

Synthesis of 2,3-dihydroquinazolin-4(1H)-ones, disulfides and sulfoxides catalyzed by a zinc complex immobilized onto functionalized mesoporous MCM-41 as a mild and efficient catalyst

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

Abstract

Zinc complex with 2-amino-3-hydroxy-pyridine ligand was immobilized onto chloropropyl-modified mesoporous silica MCM-41 (CP-MCM-41) via post-grafting method. The prepared catalyst has been characterized by low-angle X-ray diffraction, Fourier transform infrared spectroscopy, scanning electron microscopy, energy-dispersive spectrum, atomic adsorption spectroscopy and thermogravimetric analysis. The immobilized nano-structured material showed very good catalytic activity and excellent recycling efficiencies for the oxidation reaction of sulfides to sulfoxides and oxidative coupling of thiols to their corresponding disulfides in the presence of aqueous hydrogen peroxide as oxidant at room temperature and the synthesis of 2,3-dihydroquinazolin-4(1H)-one derivatives in water.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

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

Similar content being viewed by others

References

  1. S. Bhunia, S. Koner, Polyhedron 30, 1857 (2011)

    Article  CAS  Google Scholar 

  2. A. Rostami, Y. Navasi, D. Moradi, A. Ghorbani-Choghamarani, Catal. Commun. 43, 16 (2014)

    Article  CAS  Google Scholar 

  3. A. Rostami, B. Atashkar, J. Mol. Catal. A: Chem. 398, 170 (2015)

    Article  CAS  Google Scholar 

  4. P. Sivaguru, K. Bhuvaneswari, R. Ramkumar, A. Lalitha, Tetrahedron Lett. 55, 5683 (2014)

    Article  CAS  Google Scholar 

  5. C. Bowers, P.K. Dutta, J. Catal. 122, 271 (1990)

    Article  CAS  Google Scholar 

  6. M. Salavati-Niasari, Inorg. Chem. Commun. 8, 174 (2005)

    Article  CAS  Google Scholar 

  7. M.R. Maurya, S.J.J. Titinchi, S. Chand, J. Mol. Catal. A: Chem. 214, 257 (2004)

    Article  CAS  Google Scholar 

  8. F. Minutolo, D. Pini, A. Petri, P. Salvadori, Tetrahedron Asymmetry 7, 2293 (1996)

    Article  CAS  Google Scholar 

  9. S.M. Drechsel, R.C.K. Kaminski, S. Nakagaki, F. Wypych, J. Colloid Interface Sci. 277, 138 (2004)

    Article  CAS  Google Scholar 

  10. M. Salavati-Niasari, J. Mol. Catal. A 229, 159 (2005)

    Article  CAS  Google Scholar 

  11. S.B. Wang, Microporous Mesoporous Mater. 117, 1 (2009)

    Article  CAS  Google Scholar 

  12. B.G. Trewyn, S. Giri, I.I. Slowing, V.S.Y. Lin, Chem. Commun. 307, 3236 (2007)

    Article  Google Scholar 

  13. M. Manzano, M. Colilla, M. Vallet-Regi, Expert Opin. Drug Deliv. 6, 1383 (2009)

    Article  CAS  Google Scholar 

  14. C.H. Lei, P. Liu, B.W. Chen, Y.M. Mao, H. Engelmann, Y. Shin, J. Jaffar, I. Hellstrom, J. Liu, K.E. Hellstrom, J. Am. Chem. Soc. 132, 6906 (2010)

    Article  CAS  Google Scholar 

  15. Q.J. He, Z.W. Zhang, Y. Gao, J.L. Shi, Y.P. Li, Small 5, 2722 (2009)

    Article  CAS  Google Scholar 

  16. Q.J. He, J.L. Shi, M. Zhu, Y. Chen, F. Chen, Microporous Mesoporous Mater. 131, 314 (2010)

    Article  CAS  Google Scholar 

  17. A. Ghorbani-Choghamarani, F. Nikpour, F. Ghorbani, F. Havasi, RSC Adv. 5, 33212 (2015)

    Article  CAS  Google Scholar 

  18. S.L. Burkett, S.D. Sims, S. Mann, Chem. Commun. 11, 1367 (1996)

    Article  Google Scholar 

  19. D.J. Macquarrie, Chem. Commun. 16, 1961 (1996)

    Article  Google Scholar 

  20. X. Feng, G.E. Fryxell, L.-Q. Wang, A.Y. Kim, J. Liu, K.M. Kemner, Science 276, 923 (1997)

    Article  CAS  Google Scholar 

  21. L. Mercier, T.J. Pinnavaia, Adv. Mater. 9, 500 (1997)

    Article  CAS  Google Scholar 

  22. C. Venkatesan, A.P. Singh, Catal. Lett. 88, 3 (2003)

    Article  Google Scholar 

  23. Y.F. Shao, L.Z. Wang, J.L. Zhang, J. Photochem. Photobiol., A 180, 59 (2006)

    Article  CAS  Google Scholar 

  24. K. Hadjiivanov, T. Tsoncheva, M. Dimitrov, C. Minchev, H. Knozinger, Appl. Catal. A 241, 331 (2003)

    Article  CAS  Google Scholar 

  25. D. Keilin, T. Mann, J. Biochem. 34, 1163 (1940)

    Article  CAS  Google Scholar 

  26. D. Lowicki, S. Bas, J. Mlynarski, Tetrahedron 71, 1339 (2015)

    Article  CAS  Google Scholar 

  27. Q. Zeng, W. Weng, X. Xue, Inorg. Chim. Acta 388, 11 (2012)

    Article  CAS  Google Scholar 

  28. A. Ghorbani-Choghamarani, S. Sardari, Chin. J. Catal. 31, 1347 (2010)

    Article  CAS  Google Scholar 

  29. M. Khorshidifard, H. Amiri Rudbari, B. Askari, M. Sahihi, M. Riahi Farsani, F. Jalilian, G. Bruno, Polyhedron 95, 1 (2015)

    Article  CAS  Google Scholar 

  30. G. Capozzi, G. Moden, Chemistry of the Thiol Group (Wiley, London, 1974), p. 785

  31. S. Oae, Organic Sulfur Chemistry: Structure and Mechanism (CRC Press, Boca Raton, FL, 1991) vol. 113, p. 1526

  32. J. Wang, Y. Zong, R. Fu, Y. Niu, G. Yue, Z. Quan, X. Wang, Y. Pan, Ultrason. Sonochem. 21, 29 (2014)

    Article  CAS  Google Scholar 

  33. K.R. Saxena, M.A. Khan, Indian J. Chem. 26, 443 (1989)

    Google Scholar 

  34. H. Shivarama, B. Padmaja, M.T. Shivananda, M.K. Akbarali, Indian J. Chem. 37, 715 (1998)

    Google Scholar 

  35. T. Singh, V.K. Srivastava, S. Sharma, A. Kumar, Indian J. Chem. 45, 2558 (2006)

    Google Scholar 

  36. R. Tyagi, B. Goel, V.K. Srivastava, A. Kumar, Indian J. Pharm. Sci. 60, 283 (1998)

    CAS  Google Scholar 

  37. A.N. Gangwal, U.R. Kothawade, A.D. Galande, D.S. Pharande, A.S. Dhake, Indian J. Heterocycl. Chem. 10, 291 (2001)

    CAS  Google Scholar 

  38. A. Kumar, M. Tyagi, V.K. Srivastava, Indian J. Chem. 42, 2142 (2003)

    Google Scholar 

  39. A.R. Raghu Ram, R.H. Bahekar, Indian J. Chem. 38, 434 (1999)

    Google Scholar 

  40. M. Nikoorazm, A. Ghorbani-Choghamarani, N. Noori, Appl. Organomet. Chem. 29, 328 (2015)

    Article  CAS  Google Scholar 

  41. M. Nikoorazm, A. Ghorbani-Choghamarani, H. Mahdavi, S.M. Esmaeili, Microporous Mesoporous Mater. 211, 174 (2015)

    Article  CAS  Google Scholar 

  42. M. Nikoorazm, A. Ghorbani-Choghamarani, F. Ghorbani, H. Mahdavi, Z. Karamshahi, J. Porous Mater. 22, 261 (2015)

    Article  CAS  Google Scholar 

  43. A. Jabbari, H. Mahdavi, M. Nikoorazm, A. Ghorbani-Choghamarani, J. Porous Mater. 22, 1111 (2015)

    Article  CAS  Google Scholar 

  44. M. Hajjami, B. Tahmasbi, RSC Adv. 5, 59194 (2015)

    Article  CAS  Google Scholar 

  45. A.V. Dhanunjaya Rao, B.P. Vykunteswararao, T. Bhaskarkumar, N.R. Jogdand, D. Kalita, J.K.D. Lililakar, V. Siddaiah, P.D. Sanasi, A. Raghunadh, Tetrahedron Lett. 56, 4714 (2015)

    Article  CAS  Google Scholar 

  46. B.V. Labade, P.V. Shinde, M.S. Shingare, Tetrahedron Lett. 54, 5778 (2013)

    Article  CAS  Google Scholar 

  47. A. Ghorbani-Choghamarani, M. Norouzi, J. Mol. Catal. A: Chem. 395, 172 (2014)

    Article  CAS  Google Scholar 

  48. J. Safari, S. Gandomi-Ravandi, RSC Adv. 4, 11654 (2014)

    Article  CAS  Google Scholar 

  49. A. Ghorbani-Choghamarani, Z. Darvishnejad, M. Norouzi, Appl. Organomet. Chem. 29, 707 (2015)

    Article  CAS  Google Scholar 

  50. A. Ghorbani-Choghamarani, Z. Darvishnejad, B. Tahmasbi, Inorg. Chim. Acta 435, 223 (2015)

    Article  CAS  Google Scholar 

  51. G.W. Wagner, Y.C. Yang, Ind. Eng. Chem. Res. 41, 1925 (2002)

    Article  CAS  Google Scholar 

  52. A. Ghorbani-Choghamarani, G. Azadi, B. Tahmasbi, M. Hadizadeh-Hafshejani, Z. Abdi, Phosphorus, Sulfur Silicon Relat. Elem. 189, 433 (2014)

    Article  CAS  Google Scholar 

  53. A. Shaabani, A.H. Rezayan, Catal. Commun. 8, 1112 (2007)

    Article  CAS  Google Scholar 

  54. A. Ghorbani-Choghamarani, M. Nikoorazm, H. Goudarziafshar, B. Tahmasbi, Bull. Korean Chem. Soc. 30, 6 (2009)

    Google Scholar 

  55. A. Ghorbani-Choghamarani, M. Nikoorazm, G. Azadi, J. Serb. Chem. Soc. 77, 1 (2012)

    Article  Google Scholar 

  56. A. Ghorbani-Choghamarani, S. Sardari, J. Sulfur Chem. 32, 63 (2011)

    Article  CAS  Google Scholar 

  57. A. Ghorbani-Choghamarani, P. Moradi, B. Tahmasbi, RSC Adv. 6, 56458 (2016)

    Article  CAS  Google Scholar 

Download references

Acknowledgements

Financial support for this work by the research affairs of Ilam University, Ilam, Iran, is gratefully acknowledged.

Author information

Authors and Affiliations

  1. Department of Chemistry, Faculty of Science, Ilam University, P.O. Box 69315516, Ilam, Iran

    Mohsen Nikoorazm, Arash Ghorbani-Choghamarani & Maryam Khanmoradi

Authors
  1. Mohsen Nikoorazm
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Arash Ghorbani-Choghamarani
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Maryam Khanmoradi
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Mohsen Nikoorazm.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Nikoorazm, M., Ghorbani-Choghamarani, A. & Khanmoradi, M. Synthesis of 2,3-dihydroquinazolin-4(1H)-ones, disulfides and sulfoxides catalyzed by a zinc complex immobilized onto functionalized mesoporous MCM-41 as a mild and efficient catalyst. J IRAN CHEM SOC 14, 1215–1225 (2017). https://doi.org/10.1007/s13738-017-1072-6

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s13738-017-1072-6

Keywords

Search

Navigation