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Reactivity of b-Cetoesters Compounds, Synthesis of Nitrogenated Heterocycles (Derivatives of Tetrahydroacridin-9-ones and Pyrimidinone) and Biological Properties of Pyrimidinone Derivatives
Corresponding Author(s) : Y. Kouadri
Asian Journal of Chemistry,
Vol. 27 No. 10 (2015): Vol 27 Issue 10
Abstract
Ethyl 2-oxocyclohexanecarboxylate has undergone smooth condensation with arylamines under ethanol. The corresponding b-enaminoesters compounds were obtained in good yields. These compounds were then refluxed in biphenyl ether to attain the respective substituted tetrahydroacridin. The reaction of 2-amino-5,6-dimethylbenzimidazole with b-cetoesters gave access to an efficient synthesis of pyrimidinone derivatives in excellent yield. A series of novel heterocycles were prepared. Biological properties of compounds 11-14 have been distinctively evolved.
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References
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A. Frideling, R. Faure, J.-P. Galy, A. Kenz, I. Alkorta and J. Elguero, Eur. J. Med. Chem., 39, 37 (2004); doi:10.1016/j.ejmech.2003.10.003.
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A.M. Abdel‐Halim, A.M. Tawfik, S. S. Ibrahim, A.M.El‐Kazak, Indian J. Heterocycl. Chem., 3, 165 (1994).
Y.L. Chen, C.M. Lu, I.L. Chen, L.T. Tsao and J.P.J. Wang, Med. Chem., 45, 4689 (2002); doi:10.1021/jm020102v.
Y.-L. Chen, I.-L. Chen, C.-M. Lu, C.-C. Tzeng, L.-T. Tsao and J.-P. Wang, Bioorg. Med. Chem., 11, 3921 (2003); doi:10.1016/S0968-0896(03)00439-5.
J.S. Skotnicki and S.C. Gilman, Chem. Abstr., 112, 118 (1990).
M. Yamaguchi, K. Wakasugi, R. Saito, Y. Adachi, Y. Yoshikawa, H. Sakurai and A. Katoh, J. Inorg. Biochem., 100, 260 (2006); doi:10.1016/j.jinorgbio.2005.11.010.
Y.S. Sadanandam, M.M. Shetty and P.V. Diwan, Eur. J. Med. Chem., 27, 87 (1992); doi:10.1016/0223-5234(92)90066-A.
C.M. Wright, R.J. Chovatiya, N.E. Jameson, D.M. Turner, G. Zhu, S. Werner, D.M. Huryn, J.M. Pipas, B.W. Day, P. Wipf and J.L. Brodskya, Bioorg. Med. Chem., 16, 3291 (2008); doi:10.1016/j.bmc.2007.12.014.
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