Abstract
3(2-pyridinylmethylene)-5-aryl-2(3H)-furanones and 3(3-pyridinylmethylene)-5-aryl-2(3H)-furanones were prepared as a mixture of (E) and (Z) stereoisomers by condensing pyridine-2-carboxaldehyde and pyridine-3-carboxaldehyde with 3-aroylpropionic acids. The reaction of the furanones 6 and 7 with anhydrous aluminium chloride in benzene led to the formation of 4,4-diaryl-1-(2-pyridinyl)but-1,3-diene (8) and 4,4-diaryl-1-(3-pyridinyl)but-1,3-diene (9) as mixtures of geometrical (E,E- and E,Z-) stereoisomers via an intermolecular alkylation mode. When the reaction was carried out in tetrachloroethane as a solvent, the reaction of 6 gave 5-arylquinoline-7-carboxylic acid via intramolecular alkylation mode. This may be considered as a novel method for the synthesis of quinoline derivatives. J. Heterocyclic Chem., (2011).
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