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Green Synthesis of 2-Benzoyl-4-quinazolinones
Corresponding Author(s) : Qingle Zeng
Asian Journal of Chemistry,
Vol. 27 No. 3 (2015): Vol 27 Issue 3
Abstract
A catalyst-free synthesis of 2-benzoyl-4-quinazolinones is described here. Anthranilamides and a-haloacetophenones were used as the starting reagents. The effects of molar ratio of reactants, catalyst, solvent, base, temperature and time on the reaction were investigated and then the optimal reaction conditions were achieved. All of the substrates examined under the optimized conditions gave high yields. Compared to traditional synthesis method of 2-benzoyl-4-quinazolinones, this method has several advantages, such as no catalyst, cost saving and environmentally benign process.
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- M. Demeunynck and I. Baussanne, Curr. Med. Chem., 20, 794 (2013); doi:10.2174/0929867311320060006#sthash.pXF4SjPT.dpuf.
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- V.A. Rao, K. Agama, S. Holbeck and Y. Pommier, Cancer Res., 67, 9971 (2007); doi:10.1158/0008-5472.CAN-07-0804.
- M.F. Pereira, R. Chevrot, E. Rosenfeld, V. Thiery and T. Besson, Enzym. Inhib. Med. Chem., 22, 577 (2007); doi:10.1080/14756360701425345.
- B. Halova-Lajoie, V. Brumas, M.M.L. Fiallo and G. Berthon, J. Inorg. Biochem., 100, 362 (2006); doi:10.1016/j.jinorgbio.2005.12.002.
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- E.M. Berman and L.M. Werbel, J. Med. Chem., 34, 479 (1991); doi:10.1021/jm00106a001.
- S.L. Wang, J. Sheng and S.J. Tu, Chin. J. Org. Chem., 31, 1522 (2011).
- H.Y. Zhang, J. Sheng and X.S. Wang, J. Xuzhou Norm. Univ., 29, 70 (2011).
- B. Li, Z.L. Liu, J.D. Xu and D. Xiang, Modern Agrochem., 6, 14 (2004).
- M.W. Ding, S.J. Yang and Y.F. Chen, Chin. J. Org. Chem., 8, 923 (2004).
- M. Akazome, T. Kondo and Y. Watanabe, J. Org. Chem., 58, 310 (1993); doi:10.1021/jo00054a008.
- X.L. Xu, P. Lu and Y.M. Zhang, Synth. Commun., 31, 323 (2001); doi:10.1081/SCC-100000519.
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- X.W. Liu, H. Fu, Y.Y. Jiang and Y.F. Zhao, Angew. Chem. Int. Ed., 48, 348 (2009); doi:10.1002/anie.200804675.
- X. Zhang, D. Ye, H. Sun, D. Guo, J. Wang, H. Huang, X. Zhang, H.L. Jiang and H. Liu, Green Chem., 11, 1881 (2009); doi:10.1039/b916124b.
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- H. Wei, T. Li, Y. Zhou, L. Zhou and Q. Zeng, Synthesis, 45, 3349 (2013); doi:10.1055/s-0033-1340040.
References
M. Demeunynck and I. Baussanne, Curr. Med. Chem., 20, 794 (2013); doi:10.2174/0929867311320060006#sthash.pXF4SjPT.dpuf.
J. Bergman and A. Brynolf, Tetrahedron, 46, 1295 (1990); doi:10.1016/S0040-4020(01)86694-1.
T. Nomura, Z.-Z. Ma, Y. Hano and Y.-J. Chen, Heterocycles, 51, 1883 (1999); doi:10.3987/COM-99-8595.
V.A. Rao, K. Agama, S. Holbeck and Y. Pommier, Cancer Res., 67, 9971 (2007); doi:10.1158/0008-5472.CAN-07-0804.
M.F. Pereira, R. Chevrot, E. Rosenfeld, V. Thiery and T. Besson, Enzym. Inhib. Med. Chem., 22, 577 (2007); doi:10.1080/14756360701425345.
B. Halova-Lajoie, V. Brumas, M.M.L. Fiallo and G. Berthon, J. Inorg. Biochem., 100, 362 (2006); doi:10.1016/j.jinorgbio.2005.12.002.
V.J. Ram, Farhanullah, B.K. Tripathi and A.K. Srivastava, Bioorg. Med. Chem., 11, 2439 (2003); doi:10.1016/S0968-0896(03)00142-1.
E.M. Berman and L.M. Werbel, J. Med. Chem., 34, 479 (1991); doi:10.1021/jm00106a001.
S.L. Wang, J. Sheng and S.J. Tu, Chin. J. Org. Chem., 31, 1522 (2011).
H.Y. Zhang, J. Sheng and X.S. Wang, J. Xuzhou Norm. Univ., 29, 70 (2011).
B. Li, Z.L. Liu, J.D. Xu and D. Xiang, Modern Agrochem., 6, 14 (2004).
M.W. Ding, S.J. Yang and Y.F. Chen, Chin. J. Org. Chem., 8, 923 (2004).
M. Akazome, T. Kondo and Y. Watanabe, J. Org. Chem., 58, 310 (1993); doi:10.1021/jo00054a008.
X.L. Xu, P. Lu and Y.M. Zhang, Synth. Commun., 31, 323 (2001); doi:10.1081/SCC-100000519.
G.P. Cai, X.L. Xu, Z.F. Li, P. Lu and W.P. Weber, J. Heterocycl. Chem., 39, 1271 (2002); doi:10.1002/jhet.5570390623.
J.X. Chen, H.Y. Wu and W.K. Su, Chin. Chem. Lett., 18, 536 (2007); doi:10.1016/j.cclet.2007.03.037.
J.X. Chen, W.K. Su, H.Y. Wu, M. Liu and C. Jin, Green Chem., 9, 972 (2007); doi:10.1039/b700957g.
R.Z. Qiao, B.L. Xu and Y.H. Wang, Chin. Chem. Lett., 18, 656 (2007); doi:10.1016/j.cclet.2007.04.036.
M. Dabiri, P. Salehi, S. Otokesh, M. Baghbanzadeh, G. Kozehgary and A.A. Mohammadi, Tetrahedron Lett., 46, 6123 (2005); doi:10.1016/j.tetlet.2005.06.157.
M. Dabiri, P. Salehi, M. Baghbanzadeh, M.A. Zolfigol, M. Agheb and S. Heydari, Catal. Commun., 9, 785 (2008); doi:10.1016/j.catcom.2007.08.019.
J.X. Chen, D.Z. Wu, F. He, M. Liu, H. Wu, J. Ding and W. Su, Tetrahedron Lett., 49, 3814 (2008); doi:10.1016/j.tetlet.2008.03.127.
L. Zhou, L.B. Fu and K. Ding, Synthesis, 24, 3974 (2008); doi:10.1055/s-0028-1083245.
X.W. Liu, H. Fu, Y.Y. Jiang and Y.F. Zhao, Angew. Chem. Int. Ed., 48, 348 (2009); doi:10.1002/anie.200804675.
X. Zhang, D. Ye, H. Sun, D. Guo, J. Wang, H. Huang, X. Zhang, H.L. Jiang and H. Liu, Green Chem., 11, 1881 (2009); doi:10.1039/b916124b.
X. Tu, T. Li, L. Zhou, Y. Zhang and Q. Zeng, Fresenius Environ. Bull, 22, 3857 (2013).
D. Qiu, H. Wei, L. Zhou and Q. Zeng, Appl. Organomet. Chem., 28, 109 (2014); doi:10.1002/aoc.3089.
D. Zhan, T. Li, H. Wei, W. Weng, K. Ghandi and Q. Zeng, RSC Adv., 3, 9325 (2013); doi:10.1039/c3ra41370e.
H. Wei, T. Li, Y. Zhou, L. Zhou and Q. Zeng, Synthesis, 45, 3349 (2013); doi:10.1055/s-0033-1340040.