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Three Component One-Pot Synthesis of 1-Aryl-4-benzo[f]quinoline Derivatives in Glycerol
Corresponding Author(s) : Xue-Mei Wang
Asian Journal of Chemistry,
Vol. 27 No. 3 (2015): Vol 27 Issue 3
Abstract
A series of 1-aryl-1,2-dihydrobenzo[f]quinolin-3(4H)one derivatives were synthesized by one-pot muticomponent reaction of Meldrum's acid with benzaldehyde, naphthalene-2-amine in glycerol. Glycerol, a new green organic solvent, it not only acts as a catalyst but also as a recyclable solvent by significantly enhancing the intramolecular cyclization. When compared with classical methods, this method has the advantages of milder reaction conditions, good yields, easy processing and environmental benignity. All compounds were characterized by elemental analysis, FT-IR and 1H NMR spectra.
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References
L.A. Blanchard, D. Hancu, E.J. Beckman and J.F. Brennecke, Nature, 399, 28 (1999); doi:10.1038/19887.
A. Wolfson, C. Dlugy and Y. Shotland, Environ. Chem. Lett., 5, 67 (2007); doi:10.1007/s10311-006-0080-z.
Y.L. Gu, J. Barrault and F. Jérome, Adv. Synth. Catal., 350, 2007 (2008); doi:10.1002/adsc.200800328.
B.D. Palmer, H.H. Lee, P. Johnson, B.C. Baguley, G. Wickham, L.P.G. Wakelin, W.D. McFadyen and W.A. Denny, J. Med. Chem., 33, 3008 (1990); doi:10.1021/jm00173a015.
G.J. Atwell, B.F. Cain, B.C. Baguley, G.J. Finlay and W.A. Denny, J. Med. Chem., 27, 1481 (1984); doi:10.1021/jm00377a017.
K.A. Ismail and E.A. Koreish, Alex. J. Pharm. Sci., 14, 161 (2000).
R. Simsek, C. Safak, K. Erol and B. Sirmagul, Pharmazie, 56, 665 (2001).
R. Simsek, C. Safak, K. Erol, S. Ataman, M. Ulgen and A. Linden, Arzneim. Forsch.–Drug Res., 53, 159 (2003); doi:10.1055/s-0031-1297089.
N.G. Kozlov, L.I. Basalayeva and L.Y. Tychinskaya, Russ. J. Org. Chem., 38, 1166 (2002); doi:10.1023/A:1020953510529.
X.S. Wang, M.M. Zhang, Z.S. Zeng, D.Q. Shi, S.J. Tu, X.Y. Wei and Z.M. Zong, Tetrahedron Lett., 46, 7169 (2005); doi:10.1016/j.tetlet.2005.08.091.
M.M. Zhang, X.S. Wang, Q. Li, C.S. Yao and S.J. Tu, Chinese J. Org. Chem., 28, 881 (2008)..
X.M. Wang, H.L. Ye, Z.J. Qaun and X.C. Wang, Res. Chem. Intermed., 39, 2357 (2013); doi:10.1007/s11164-012-0762-z.
D. Davidson and S.A. Bernhard, J. Am. Chem. Soc., 70, 3426 (1948); doi:10.1021/ja01190a060.