Skip to main content
SpringerLink
Log in

Efficient synthesis of mono- and disubstituted 2,3-dihydroquinazolin-4(1H)-ones using aluminum methanesulfonate as a reusable catalyst

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

Abstract

A wide range of mono- and disubstituted 2,3-dihydroquinazolin-4(1H)-ones were synthesized via a one-pot three components condensation of isatoic anhydride, aldehydes, and ammonium salts or primary amines in the presence of aluminum methanesulfonate in EtOH/H2O solution. The catalyst is reusable and could be recycled for several runs without any distinct decrease in its efficiency. A plausible mechanism for this one-pot three components reaction was proposed.

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

Similar content being viewed by others

References

  1. Y.S. Sadanandam, K.R.M. Reddy, A.B. Rao, Eur. J. Med. Chem. 22, 169 (1987)

    Article  CAS  Google Scholar 

  2. E. Hamel, C.M. Lin, J. Plowman, H.K. Wang, K.H. Lee, K.D. Paull, Biochem. Pharmacol. 51, 53 (1996)

    Article  CAS  Google Scholar 

  3. 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)

    Article  CAS  Google Scholar 

  4. R.J. Alaimo, H.E. Russell, J. Med. Chem. 15, 335 (1972)

    Article  CAS  Google Scholar 

  5. H.A. Parish, R.D. Gilliom, W.P. Purcell, R.K. Browne, R.F. Spirk, H.D. White, J. Med. Chem. 25, 98 (1982)

    Article  CAS  Google Scholar 

  6. M. Bakavoli, O. Sabzevari, M. Rahimizadeh, Chin. Chem. Lett. 18, 1466 (2007)

    Article  CAS  Google Scholar 

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

    Article  CAS  Google Scholar 

  8. K. Hattori, Y. Kido, H. Yamamoto, J. Ishida, K. Kamijo, K. Murano, M. Ohkubo, T. Kinoshita, A. Iwashita, K. Mihara, S. Yamazaki, N. Matsuoka, Y. Teramura, H. Miyake, J. Med. Chem. 47, 4151 (2004)

    Article  CAS  Google Scholar 

  9. S.D. Sharma, V. Kaur, Synthesis 677 (1989)

  10. G.P. Cai, X.L. Xu, Z.F. Li, W.P. Weber, P. Lu, J. Heterocycl. Chem. 39, 1271 (2002)

    Article  CAS  Google Scholar 

  11. D.Q. Shi, L. Rong, J.X. Wang, Q.Y. Zhuang, X.S. Wang, H.W. Hu, Tetrahedron Lett. 44, 3199 (2003)

    Article  CAS  Google Scholar 

  12. A. Shaabani, A. Maleki, H. Mofakham, Synth. Commun. 38, 3751 (2008)

    Article  CAS  Google Scholar 

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

    Article  CAS  Google Scholar 

  14. Y.X. Zong, Y. Zhao, W.C. Luo, X.H. Yu, J.K. Wang, Y. Pan, Chin. Chem. Lett. 21, 778 (2010)

    Article  CAS  Google Scholar 

  15. M. Abdollahi-Alibeik, E. Shabani, Chin. Chem. Lett. 22, 1163 (2011)

    CAS  Google Scholar 

  16. V.B. Rao, C.V. Ratnam, Indian J. Chem. Sect. B 18B, 409 (1979)

    CAS  Google Scholar 

  17. A. Davoodnia, M. Bakavoli, F. Khorramdelan, M. Roshani, Indian J. Heterocycl. Chem. 16, 147 (2006)

    CAS  Google Scholar 

  18. M. Dabiri, P. Salehi, S. Otokesh, M. Baghbanzadeh, G. Kozehgary, A.A. Mohammadi, Tetrahedron Lett. 46, 6123 (2005)

    Article  CAS  Google Scholar 

  19. P. Salehi, M. Dabiri, M.A. Zolfigol, M. Baghbanzadeh, Synlett 1155 (2005)

  20. M. Baghbanzadeh, P. Salehi, M. Dabiri, G. Kozehgary, Synthesis 344 (2006)

  21. Z. Karimi-Jaberi, R. Arjmandi, Monatsh. Chem. 142, 631 (2011)

    Article  CAS  Google Scholar 

  22. L.M. Wang, L. Hu, J.H. Shao, J.J. Yu, L. Zhang, J. Fluor. Chem. 129, 1139 (2008)

    Article  CAS  Google Scholar 

  23. J.X. Chen, D.Z. Wu, F. He, M. Liu, H.Y. Wu, J.C. Ding, W.K. Su, Tetrahedron Lett. 49, 3814 (2008)

    Article  CAS  Google Scholar 

  24. J.X. Chen, W.K. Su, H.Y. Wu, M. Liu, C. Jin, Green Chem. 9, 972 (2007)

    Article  CAS  Google Scholar 

  25. M. Dabiri, P. Salehi, M. Baghbanzadeh, Monatsh. Chem. 138, 1191 (2007)

    Article  CAS  Google Scholar 

  26. P. Salehi, M. Dabiri, M. Baghbanzadeh, M. Bahramnejad, Synth. Commun. 36, 2287 (2006)

    Article  CAS  Google Scholar 

  27. S.M. Roopan, F.N. Khan, J.S. Jin, R.S. Kumar, Res. Chem. Intermed. 37, 919 (2011)

    Article  CAS  Google Scholar 

  28. H.R. Shaterian, A.R. Oveisi, M. Honarmand, Synth. Commun. 40, 1231 (2010)

    Article  CAS  Google Scholar 

  29. M. Dabiri, P. Salehi, M. Bahramnejad, M. Alizadeh, Monatsh. Chem. 141, 877 (2010)

    Article  CAS  Google Scholar 

  30. L.Y. Zeng, C. Cai, J. Heterocycl. Chem. 47, 1035 (2010)

    Article  CAS  Google Scholar 

  31. M.P. Surpur, P.R. Singh, S.B. Patil, S.D. Samant, Synth. Commun. 37, 1965 (2007)

    Article  CAS  Google Scholar 

  32. M. Dabiri, P. Salehi, M. Baghbanzadeh, M.A. Zolfigol, M. Agheb, S. Heydari, Catal. Commun. 9, 785 (2008)

    Article  CAS  Google Scholar 

  33. N. Khodabakhsh, M. Mohammad, R.M. Salimeh, Chin. J. Chem. 29, 1417 (2011)

    Article  Google Scholar 

  34. M.Z. Kassaee, S. Rostamizadeh, N. Shadjou, E. Motamedi, M. Esmaeelzadeh, J. Heterocycl. Chem. 47, 1421 (2010)

    Article  CAS  Google Scholar 

  35. Z.H. Zhang, H.Y. Lu, S.H. Yang, J.W. Gao, J. Comb. Chem. 12, 643 (2010)

    Article  CAS  Google Scholar 

  36. A. Saffar-Teluri, S. Bolouk, Monatsh. Chem. 141, 1113 (2010)

    Article  CAS  Google Scholar 

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

  38. M. Ghashang, K. Azizi, H. Moulavi-Pordanjani, H.R. Shaterian, Chin. J. Chem. 29, 1617 (2011)

    Article  Google Scholar 

  39. K. Niknam, N. Jafarpour, E. Niknam, Chin. Chem. Lett. 22, 69 (2011)

    Article  CAS  Google Scholar 

  40. M. Wang, Z.C. Wang, Z.L. Sun, H. Jiang, React. Kinet. Catal. Lett. 84, 223 (2005)

    Article  CAS  Google Scholar 

  41. M. Wang, Z.C. Wang, Z.L. Sun, H. Jiang, Transit. Met. Chem. 30, 792 (2005)

    Article  CAS  Google Scholar 

  42. M. Wang, H. Gong, H. Jiang, Z.C. Wang, Synth. Commun. 36, 1953 (2006)

    Article  CAS  Google Scholar 

  43. M. Wang, Z.G. Song, H. Gong, H. Jiang, Chin. Chem. lett. 18, 799 (2007)

    Article  CAS  Google Scholar 

  44. M. Wang, Z.G. Song, H. Jiang, Org. Prep. Proc. Int. 41, 315 (2009)

    Article  CAS  Google Scholar 

  45. M. Wang, Z.G. Song, T.T. Zhang, Monatsh. Chem. 141, 993 (2010)

    Article  CAS  Google Scholar 

  46. M. Wang, T.T. Zhang, Z.G. Song, Chin. Chem. Lett. 22, 427 (2011)

    Article  CAS  Google Scholar 

Download references

Acknowledgment

This research work was financially supported by the Committee of Science and Technology of Liaoning Province of China (No. 20091001).

Author information

Authors and Affiliations

  1. Center for Science & Technology Experiment, Bohai University, Jinzhou, 121000, People’s Republic of China

    Zhiguo Song, Lianli Liu, Yang Wang & Xiaohu Sun

Authors
  1. Zhiguo Song
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Lianli Liu
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Yang Wang
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Xiaohu Sun
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Zhiguo Song.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Song, Z., Liu, L., Wang, Y. et al. Efficient synthesis of mono- and disubstituted 2,3-dihydroquinazolin-4(1H)-ones using aluminum methanesulfonate as a reusable catalyst. Res Chem Intermed 38, 1091–1099 (2012). https://doi.org/10.1007/s11164-011-0445-1

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11164-011-0445-1

Keywords

Search

Navigation