First synthesis of 2-(benzofuran-2-yl)-6,7-methylene dioxyquinoline-3-carboxylic acid derivatives

A facile and inexpensive synthesis of a series of novel methylenedioxy-bearing 2-(benzofuran-2-yl)-quinoline-3-carboxylic acid derivatives 3a–h via the one-pot reaction of ethyl 2-chloromethyl-6,7-methylenedioxyquinoline-3-carboxylate (5) with various substituted salicylaldehydes 6a–g as well as 2-hydroxy-1-naphthaldehyde (6h) is described. Substrate 5 was synthesized by the Friedländer condensation reaction of 2-amino-4,5-methylenedioxybenzaldehyde (4) with ethyl 4-chloro-3-oxobutanoate using KHSO(4) as catalyst under ultrasound irradiation conditions. The targeted compounds 3a–h were obtained in good yields of 52–82% and their structures were established based on spectral data and elemental analyses.