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Structurally diversified synthesis of 2,3-dihydroquinazolin-4-(1H)-ones from 2-aminobenzamides and 1,2-dicarbonyl compounds in ionic liquids catalyzed by iodine

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Abstract

A green procedure for the rapid diversification of quinazolin-4-(1H)-one scaffolds is described in this paper. Various types of 1,2-dicarbonyl compounds are treated with 2-aminobenzamides in ionic liquids catalyzed by iodine and unexpectedly afford structurally diversified single-quinazoline derivatives. The recyclability of the ionic liquids makes this protocol to be an environmentally benign procedure.

Graphical Abstract

A total of 39 quinazolin-4-(1H)-one scaffolds were synthesized via a green procedure of 1,2-dicarbonyl compounds and 2-aminobenzamides in ionic liquids catalyzed by iodine.

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References

  1. E.A. Henderson, V. Bavetsias, D.S. Theti, S.C. Wilson, R. Clauss, A.L. Jackman, Bioorg. Med. Chem. 14, 5020 (2006)

    Article  CAS  Google Scholar 

  2. T.C. Chien, C.S. Chen, F.H. Yu, J.W. Chern, Chem. Pharm. Bull. 52, 1422 (2004)

    Article  CAS  Google Scholar 

  3. Y.S. Lee, H.K. Park, J.Y. Lee, B.S. Yang, S.H. Suh, Preparation of 4-phenylamino-[1,4]dioxano[2,3-g]quinazolines as tyrosine kinase inhibitors. Jpn. Kokai Tokkyo Koho 2003, JP 2003026682 A 20030129

  4. G.F. Xu, B.A. Song, P.S. Bhadury, S. Yang, P.Q. Zhang, L.H. Jin, W. Xue, D.Y. Hu, P. Lu, Bioorg. Med. Chem. 15, 37682 (2007)

    Google Scholar 

  5. P.R. Marsham, L.R. Hughes, A.L. Jackman, A.J. Hayter, J. Oldfield, J.M. Wardleworth, J.A.M. Bishop, B.M. O’Connor, A.H. Calvert, J. Med. Chem. 34, 1594 (1991)

    Article  CAS  Google Scholar 

  6. K. Waisser, J.V. Gregor, H. Dostal, J. Kunes, L. Kubicova, V. Klimesova, J. Kaustova, Farmaco 56, 803 (2001)

    Article  CAS  Google Scholar 

  7. I. Khan, A. Ibrar, N. Abbas, A. Saeed, Eur. J. Med. Chem. 76, 193 (2014)

    Article  CAS  Google Scholar 

  8. I. Khan, A. Ibrar, W. Ahmed, A. Saeed, Eur. J. Med. Chem. 90, 124 (2015)

    Article  CAS  Google Scholar 

  9. I. Khan, S. Zaib, S. Batool, N. Abbas, Z. Ashraf, J. Iqbal, A. Saeed, Bioorg. Med. Chem. 24, 2361 (2016)

    Article  CAS  Google Scholar 

  10. T.M. Maiden, J.P. Harrity, Org. Biomol. Chem. 14, 8014 (2016)

    Article  CAS  Google Scholar 

  11. B. Moy, P. Kirkpatrick, S. Kar, P. Goss, Nat. Rev. Drug Discov. 6, 431 (2007)

    Article  CAS  Google Scholar 

  12. J.B. Koepfli, J.F. Mead, J.A. Brockman, J. Am. Chem. Soc. 69, 1837 (1947)

    Article  CAS  Google Scholar 

  13. J.B. Koepfli, J.F. Mead, J.A. Brockman, J. Am. Chem. Soc. 69, 1848 (1947)

    Article  Google Scholar 

  14. S. Yoshida, T. Aoyagi, S. Harada, N. Matsuda, T. Ikeda, H. Naganawa, M. Hamada, T. Takeuchi, J. Antibiot. 441, 111 (1991)

    Article  Google Scholar 

  15. Z.Z. Ma, Y. Hano, T. Nomura, Y.J. Chen, Heterocycles 46, 541 (1997)

    Article  CAS  Google Scholar 

  16. Y.H. Deng, R. Xu, Y. Yang, J. Chin. Pharm. Sci. 9, 116 (2000)

    CAS  Google Scholar 

  17. C. Wattanapiromsakul, P.I. Forster, P.G. Waterman, Phytochemistry 64, 609 (2003)

    Article  CAS  Google Scholar 

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

    Article  CAS  Google Scholar 

  19. F. Liu, X. Chen, A. Allali-Hassani, A.M. Quinn, T.J. Wigle, G.A. Wasney, A. Dong, G. Senisterra, I. Chau, A. Siarheyeva, J. Med. Chem. 53, 5844 (2010)

    Article  CAS  Google Scholar 

  20. J.W. Lockman, B.R. Murphy, D.F. Zigar, W.R. Judd, P.M. Slattum, Z.H. Gao, K. Ostanin, J. Green, R. McKinnon, R.T. Terry-Lorenzo, J. Med. Chem. 53, 8734 (2010)

    Article  CAS  Google Scholar 

  21. I. Beria, D. Ballinari, J.A. Bertrand, D. Borghi, T. Bossi Roberto, M.G. Brasca, P. Cappella, M. Caruso, W. Ceccarelli, A. Ciavolella, J. Med. Chem. 53, 3532 (2010)

    Article  CAS  Google Scholar 

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

    Article  CAS  Google Scholar 

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

    Article  CAS  Google Scholar 

  24. D. Rambabu, S.K. Kumar, B.Y. Sreenivas, S. Sandra, A. Kandale, P. Misra, M.V.B. Rao, M. Pal, Tetrahedron Lett. 54, 495 (2013)

    Article  CAS  Google Scholar 

  25. G.-C. Arash, T. Tahereh, Lett. Org. Chem. 8, 470 (2011)

    Article  Google Scholar 

  26. P.V. Murthy, D. Rambabu, G.R. Krishna, C.M. Reddy, K.R.S. Prasad, M.V.B. Rao, M. Pal, Tetrahedron Lett. 53, 863 (2012)

    Article  CAS  Google Scholar 

  27. 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 

  28. P.P. Naidu, A. Raghunadh, K.R. Rao, R. Mekala, J.M. Babu, B.R. Rao, V. Siddaiah, M. Pal, Synth. Commun. 44, 1475 (2014)

    Article  CAS  Google Scholar 

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

    Article  CAS  Google Scholar 

  30. K.R. Rao, R. Mekala, A. Raghunadh, S.B. Meruva, S.P. Kumar, D. Kalita, E. Laxminarayana, B. Prasad, M. Pal, RSC Adv. 5, 61575 (2015)

    Article  CAS  Google Scholar 

  31. K.R. Rao, A. Raghunadh, R. Mekala, S.B. Meruva, T.V. Pratap, T. Krishna, D. Kalita, E. Laxminarayana, B. Prasad, M. Pal, Tetrahedron Lett. 55, 6004 (2014)

    Article  CAS  Google Scholar 

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

    Article  CAS  Google Scholar 

  33. X.S. Wang, K. Yang, J. Zhou, S.J. Tu, J. Comb. Chem. 12, 417 (2010)

    Article  CAS  Google Scholar 

  34. X.S. Wang, J. Sheng, L. Lu, K. Yang, Y.L. Li, Acs Comb. Sci. 13, 196 (2011)

    Article  Google Scholar 

  35. L. Lu, M.M. Zhang, H. Jiang, X.S. Wang, Tetrahedron Lett. 54, 757 (2013)

    Article  CAS  Google Scholar 

  36. M.M. Zhang, L. Lu, X.S. Wang, J. Heterocycl. Chem. 51, 1363 (2014)

    Article  CAS  Google Scholar 

  37. L.H. Wang, P. Wang, Guangxi Qinggongye 10, 33 (2009)

    Google Scholar 

  38. M. Bakavoli, O. Sabzevari, M. Rahimizadeh, Chin. Chem. Lett. 18, 533 (2007)

    Article  CAS  Google Scholar 

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Acknowledgements

We are grateful to the National Natural Science foundation of China (20802061), the Major Natural Science Foundation of Jiangsu Province (14KJA150004), and a project funded by the Priority Academic Program Development of Jiangsu Higher Education Institutions for financial support.

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Authors and Affiliations

  1. School of Chemistry and Chemical Engineering, Jiangsu Key Laboratory of Green Synthetic Chemistry for Functional Materials, Jiangsu Normal University, Xuzhou, 221116, Jiangsu, People’s Republic of China

    Jie Wang, Mei-Mei Zhang & Xiang-Shan Wang

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  1. Jie Wang
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  2. Mei-Mei Zhang
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  3. Xiang-Shan Wang
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Correspondence to Xiang-Shan Wang.

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Wang, J., Zhang, MM. & Wang, XS. Structurally diversified synthesis of 2,3-dihydroquinazolin-4-(1H)-ones from 2-aminobenzamides and 1,2-dicarbonyl compounds in ionic liquids catalyzed by iodine. Res Chem Intermed 43, 2985–3005 (2017). https://doi.org/10.1007/s11164-016-2807-1

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