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Microwave-assisted Synthesis of 2-Methyl-4-Quinolinones via Combes Synthesis Catalyzed by Acidic Resin under Solvent-Free Condition
Corresponding Author(s) : Shizhen Yuan
Asian Journal of Chemistry,
Vol. 25 No. 10 (2013): Vol 25 Issue 10
Abstract
A simple and efficient method for the synthesis of 2-methylquinolin-4(1H)-one derivatives using NKC-9-resin as reusable eco-friendly catalyst via Combes cyclization under solvent-free and microwave irradiation conditions is described. The quinolines were obtained in high yields and in short reaction times.
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References
T.R. Verhoeven, P.J. Reider, M. Labelle, J.Y. Gauthier, Y.B. Xiang and R.J. Zamboni, J. Org. Chem., 61, 3398 (1996).
A. Sparatore, N. Basilico, S. Parapini, S. Romeo, F. Novelli and F. Sparatorec, J. Biol. Med. Chem., 13, 5338 (2005).
D. Dubé, M. Blouin, C. Brideau, C.-C. Chan, S. Desmarais, D. Ethier, J.-P. Falgueyret, R.W. Friesen, M. Girard, Y. Girard, J. Guay, D. Riendeau, P. Tagari and R.N. Young, Bioorg. Med. Chem. Lett., 8, 1255 (1998).
T.R. Govindachari, K.R. Ravindranath and N. Viswanathan, J. Chem. Soc., Perkin Trans. I, 1215 (1974).
S.A. Jenekhe, L. Lu and M.M. Alam, Macromolecules, 34, 7315 (2001).
Z.H. Skraup, Chem. Ber., 13, 2086 (1880).
R. Hauser and G.A. Reynolds, J. Am. Chem. Soc., 70, 2402 (1948).
M. Conrad and L. Limpach, Chem. Ber., 20, 944 (1887).
O. Döebner and W.V. Miller, Chem. Ber., 16, 246 (1883).
A. Combes, Bull. Soc. Chim. Fr., 49, 89 (1888).
P. Friedlander, Chem. Ber., 15, 2572 (1882).
K. Mogilaiah, K. Vidya and T.K. Swamy, Indian J. Chem., 48B, 599 (2009).
B. Sapkal, K.F. Shelke, B.B. Shingate and M.S. Shingare, J. Korean Chem. Soc., 54, 723 (2010).