Tuesday, 11 October 2011

1P26: x) Synthesis of vanillin ethers from 4-(bromomethyl) coumarins as anti-inflammatory agents


M. Ghate et al.64 treated 4-(Bromomethyl) coumarins (145) with vanillins, (146) give the corresponding ethers (147), which underwent Knovenagel condensation with ethyl cyanoacetate resulting in the formation of ethers (149) contain an active methylene group and the ortho carbonyl group. Ethers (149), when refluxed in alcoholic potassium carbonate underwent an intramolecular aldol reaction leading to the formation of 4-(7’-methoxy 2’-benzo[b]furanyl)coumarins (150) and the aryloxymethyl Coumarin (148) with p-formyl group were found to be most active as shown in scheme 26.




























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64. M. Ghate, D. Manohar, V. Kulkarni, R. Shobha, and S. Y. Kattimani, Eur. J. Med. Chem., 2003, 38, 297.
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