Skip to main content
Log in

Aluminium exchanged Indian clay as an efficient reusable green catalyst for synthesis of 2, 3-dihydroquinazolin-4(1H)-one derivatives

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

Abstract

Aluminium exchanged Indian clay (Al3+-ExIC) catalyzed synthesis of 2, 3-dihydroquinazolin-4(1H)-one derivatives in good to excellent yields has been reported. The catalyst has been characterized for its physico-chemical properties. Effects of solvent, molar ratio, amount of catalyst and reaction time on the yield of 2-phenyl-2, 3-dihydroquinazolin-4(1H)-one and recyclability of the catalyst have been investigated. Various 2, 3-dihydroquinazolin-4(1H)-one derivatives have been obtained in good to excellent yields.

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.

Institutional subscriptions

Scheme 1
Fig. 1
Fig. 2
Fig. 3
Fig. 4
Fig. 5
Fig. 6
Fig. 7
Fig. 8
Fig. 9
Fig. 10

Similar content being viewed by others

References

  1. P. Laszlo, Acc. Chem. Res 19, 121 (1984)

    Article  Google Scholar 

  2. V.S. Gerard, F. Notheisz, Heterogeneous Catalysis in Organic Chemistry, (Elsevier, San Diego, 2000)

    Google Scholar 

  3. G. Nagendrappa, Appl. Clay Sci. 53, 106 (2011)

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

    CAS  Google Scholar 

  7. 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 

  8. 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)

    Article  CAS  Google Scholar 

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

    Article  CAS  Google Scholar 

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

    Article  CAS  Google Scholar 

  11. N.B. Darvatkar, S.V. Bhilare, A.R. Deorukhkar, D.G. Raut, M.M. Salunkhe, Green Chem. Lett. Rev. 3, 301 (2010)

    Article  CAS  Google Scholar 

  12. B.V.S. Reddy, A. Venkateswarlu, Ch.. Madan, A. Vinu, Tetrahedron Lett 52, 1891 (2011)

    Article  Google Scholar 

  13. R.J. Abdel-Jalil, W. Voelter, M. Saeed, Tetrahedron Lett 45, 3475 (2004)

    Article  CAS  Google Scholar 

  14. A. Ghorbani-Choghamarani, G. Azadi, RSC Adv. 5, 9752 (2015)

    Article  CAS  Google Scholar 

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

    Article  CAS  Google Scholar 

  16. N. Razavi, B. Akhlaghinia, New J. Chem. 40, 447 (2016)

    Article  CAS  Google Scholar 

  17. S. Tarannum, N. Ahmed, Z.N. Siddiqui, Catal. Commun. 66, 60 (2015)

    Article  CAS  Google Scholar 

  18. S. Rostamizadeh, A.M. Amani, R. Aryan, H.R. Ghaieni, N. Shadjou, Synth. Commun. 38, 3567 (2008)

    Article  CAS  Google Scholar 

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

    Article  CAS  Google Scholar 

  20. F. Havasi, A. Ghorbani-Choghamarani, F. Nikpour, Microporous Mesoporous Mater 224, 26 (2016)

    Article  CAS  Google Scholar 

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

    Article  CAS  Google Scholar 

  22. M. Rahman, I. Ling, N. Abdullah, R. Hashim, A. Hajra, RSC Adv. 5, 7755 (2015)

    Article  CAS  Google Scholar 

  23. C.L. Yoo, J.C. Fettinger, M.J. Kurth, J. Org. Chem. 70, 6941 (2005)

    Article  CAS  Google Scholar 

  24. 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 

  25. G.M. Chinigo, M. Paige, S. Grindrod, E. Hamel, S. Dakshanamurthy, M. Chruszcz, W. Minor, L. Milton, M.L. Brown, J. Med. Chem. 51, 4620 (2008)

    Article  CAS  Google Scholar 

  26. Y. Chen, W. Shan, M. Lei, L. Hu, Tetrahedron Lett. 53, 5923 (2012)

    Article  CAS  Google Scholar 

  27. S. Zhaleh, N. Hazeri, M.T. Maghsoodlou, Res. Chem. Intermed. 42, 6381 (2016)

    Article  CAS  Google Scholar 

  28. A. Magyar, Z. Hell, Catal. Lett. 146, 1153 (2016)

    Article  CAS  Google Scholar 

  29. B. Vijayakumar, C.R. Reddy, P. Iyengar, G. Nagendrappa, B.S. Jai Prakash, Indian J. Chem. Technol. 12, 316 (2005)

    CAS  Google Scholar 

  30. B. Vijayakumar, N. Mahadevaiah, G. Nagendrappa, B.S. Jai Prakash. J. Porous Mater 19, 201 (2012)

    Article  CAS  Google Scholar 

  31. B. Vijayakumar, G. Nagendrappa, B.S. Jai Prakash. Catal. Lett. 128, 183 (2009)

    Article  CAS  Google Scholar 

  32. O.M. Sadek, W.K. Mekhamer, Thermochim. Acta 363, 47 (2000)

    Article  CAS  Google Scholar 

  33. K.S.W. Sing, D.H. Everett, R.A.W. Haul, L. Moscou, R.A. Pierotti, J. Rouquerol, T. Siemieniewska, Pure Appl. Chem. 57, 603 (1985)

    Article  CAS  Google Scholar 

  34. B. Vijayakumar, G. Ranga Rao, J. Porous Mater 19, 233 (2012)

    Article  CAS  Google Scholar 

  35. C.R. Reddy, Y.S. Bhat, G. Nagendrappa, B.S. Jai Prakash, Catal. Today 141, 157 (2009)

    Article  CAS  Google Scholar 

  36. S.A. Bagshaw, R.P. Cooney, Chem. Mater 5, 1101 (1993)

    Article  CAS  Google Scholar 

  37. J. Chen, W. Su, H. Wu, M. Liu, C. Jin, Green Chem. 9, 972 (2007)

    Article  CAS  Google Scholar 

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

    Article  CAS  Google Scholar 

  39. J. Safari, S. Gandomi-Ravandi, J. Mol. Catal. A 390, 1 (2014)

    Article  CAS  Google Scholar 

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

    Article  CAS  Google Scholar 

  41. J. Chen, D. Wu, F. He, M. Liu, H. Wu, J. Ding, W. Su, Tetrahedron Lett. 49, 3814 (2008)

    Article  CAS  Google Scholar 

  42. N. Kausar, I. Roy, D. Chattopadhyay, A.R. Das, RSC Adv. 6, 22220 (2016)

    Google Scholar 

Download references

Acknowledgements

This work is funded by the Department of Science and Technology-SERB, New Delhi, India, under Fast Track Scheme for Young Scientists (Project No.SB/FT/CS-089/2012). The authors wish to express their grateful thanks to the Management of Vel Tech High Tech Dr.RR Dr.SR Engineering College for the laboratory facilities provided.

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to Vijayakumar Badathala.

Electronic supplementary material

Below is the link to the electronic supplementary material.

Supplementary material 1 (DOC 27791 KB)

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Kancherla, M., Badathala, V. Aluminium exchanged Indian clay as an efficient reusable green catalyst for synthesis of 2, 3-dihydroquinazolin-4(1H)-one derivatives. J Porous Mater 24, 1187–1196 (2017). https://doi.org/10.1007/s10934-016-0358-x

Download citation

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10934-016-0358-x

Keywords

Navigation