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Synthesis of 2-aryl-2,3-dihydroquinazolin-4(1H)-ones using boric acid-functionalized MCM-41 as a novel heterogeneous catalyst under solvent-free condition

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Abstract

Ordered mesoporous silica material MCM-41 with covalently anchored boric acid groups located inside the mesochannels has been utilized as an acid catalyst for the ‘green’ synthesis of 2-aryl-2,3-dihydroquinazolin-4(1H)-one derivatives under solvent-free condition. This novel synthetic method offers advantages, such as excellent yields, simple reaction procedure, short reaction times and mild reaction conditions.

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References

  1. A.R. Katritzky, C.W. Rees, E.F.V. Scriven, Comprehensive heterocyclic chemistry II (Pergamon, Oxford, 1996)

    Google Scholar 

  2. D.A. Horton, G.T. Bourne, M.L. Smythe, Chem. Rev. 103, 893 (2003)

    Article  CAS  Google Scholar 

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

    Article  CAS  Google Scholar 

  4. V. Alagarsamy, S.V. Raja, K. Dhanabal, Bioorg. Med. Chem. 15, 235 (2007)

    Article  CAS  Google Scholar 

  5. V. Alagarsamy, U.S. Pathak, Bioorg. Med. Chem. 15, 3457 (2007)

    Article  CAS  Google Scholar 

  6. S. Eguchi, Top. Heterocycl. Chem. 6, 113 (2006)

    CAS  Google Scholar 

  7. L.H. Klemm, T.J.R. Weakley, R.D. Gilbertson, Y.H. Song, J. Heterocycl. Chem. 35, 1269 (1998)

    Article  CAS  Google Scholar 

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

  9. Z.K. Jaberi, L. Zarei, S. Afr, J. Chem. 65, 36 (2012)

    Google Scholar 

  10. A.G. Choghamarani, T. Taghipour, L. Org. Chem. 8, 470 (2011)

    Article  Google Scholar 

  11. R.A. Bunce, B. Nammalwar, J. Heterocycl. Chem. 48, 991 (2011)

    Article  CAS  Google Scholar 

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

    Article  CAS  Google Scholar 

  13. J. Zhou, J. Fang, J. Org. Chem. 76, 7730 (2011)

    Article  CAS  Google Scholar 

  14. 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 

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

    Article  CAS  Google Scholar 

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

    Article  CAS  Google Scholar 

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

    Article  CAS  Google Scholar 

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

    Article  CAS  Google Scholar 

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

    Article  CAS  Google Scholar 

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

    Article  CAS  Google Scholar 

  21. B.A. Dar, A.K. Sahu, P. Patidar, P.R. Sharma, N. Mupparapu, D. Vyas, S. Maity, M. Sharma, B. Singh, J. Ind. Eng. Chem. 19, 407 (2013)

    Article  CAS  Google Scholar 

  22. K. Ramesh, K. Karnakar, G. Satish, K.H.V. Reddy, Y.V.D. Nageswar, Tetrahedron Lett. 53, 6095 (2012)

    Article  CAS  Google Scholar 

  23. H.R. Lobo, B.S. Singh, G.S. Shankarling, Catal. Commun. 27, 179 (2012)

    Article  CAS  Google Scholar 

  24. P. Trens, M.L. Russell, L. Spjuth, M.J. Hudson, J. Liljenzin, Mater. Interf. 41, 5220 (2002)

    CAS  Google Scholar 

  25. K. Sivakumar, A. Kathirvel, A. Lalitha, Tetrahedron Lett. 51, 3018 (2010)

    Article  CAS  Google Scholar 

  26. R.D. Ruiter, K. Famine, A.P.M. Kentgens, J.C. Jansen, H. Van-Bekkum, Zeolites 13, 611 (1993)

    Article  Google Scholar 

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

    Article  CAS  Google Scholar 

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

    Article  CAS  Google Scholar 

  29. P. VNS Murthy, D. Rambabu, G. Rama Krishna, C. Malla Reddy, K.R.S. Prasad, M.V. Basaveswara Rao, M. Pal, Tetrahedron Lett. 53, 863 (2012)

    Article  Google Scholar 

  30. 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 

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

    Article  CAS  Google Scholar 

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

    Article  CAS  Google Scholar 

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

    Article  CAS  Google Scholar 

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

    Article  CAS  Google Scholar 

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

    Article  CAS  Google Scholar 

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

    Article  CAS  Google Scholar 

  37. I. Yavari, S. Beheshti, J. Iran. Chem. Soc. 8, 1030 (2011)

    Article  CAS  Google Scholar 

  38. R.B.V. Subba, A. Venkateswarlu, C. Madan, A. Venu, Tetrahedron Lett. 52, 1891 (2011)

    Article  Google Scholar 

  39. A.K. Ghosh, G. Curthoys, J. Chem. Soc. Faraday Trans. 1(79), 805 (1983)

    Article  Google Scholar 

  40. T. Xiu, Q. Liu, J. Wang, Mater. Chem. Phys. 105, 10 (2007)

    Article  CAS  Google Scholar 

  41. V. Sundaramurthy, I. Eswaramoorthi, N. Lingappan, Can. J. Chem. 82, 631 (2004)

    Article  CAS  Google Scholar 

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Acknowledgments

A.L. and P.S. gratefully acknowledge the CSIR, New Delhi, India, for providing financial assistance in the form of major research project (No. 02(0025)/11/EMR-II) and P.V. thanks UGC, Hyderabad, India, for financial support rendering by minor research project (F. No: MRP/SERO/3817/11).

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Correspondence to Appaswami Lalitha.

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Sivaguru, P., Parameswaran, K., Kiruthiga, M. et al. Synthesis of 2-aryl-2,3-dihydroquinazolin-4(1H)-ones using boric acid-functionalized MCM-41 as a novel heterogeneous catalyst under solvent-free condition. J IRAN CHEM SOC 12, 95–100 (2015). https://doi.org/10.1007/s13738-014-0459-x

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