Microwave Assisted Synthesis of N-Substituted-7-hydroxy-4-methyl-2-oxoquinolines as Anticonvulsant Agents
The reaction of resorcinol with ethylacetoacetate yielded the 7-hydroxy-4-methyl coumarin (1), which on treatment with benzidine gives 1-(4ʹ-amino-biphenyl-4-yl)-7-hydroxy-4-methyl-1H-quinolin-2-one (2). 1-{4ʹ-[(Substituted benzylidene)-amino]-biphenyl-4-yl}-7-hydroxy-4-methyl-1H-quinolin-2-one (3a-j) were obtained by reacting 1-(4ʹ-amino-biphenyl-4-yl)-7-hydroxy-4-methyl-1H-quinolin-2-one (2) with different substituted aromatic aldehydes in presence of glacial acetic acid by microwave irradiation. The compound 1-{4ɴ-[(substituted benzylidene)-amino]-biphenyl-4-yl}-7-hydroxy-4-methyl-1H-quinolin-2-one (3a-j) on cyclization with chloro acetyl chloride in presence of triethylamine as catalyst under microwave irradiation furnished 1-{4ʹ-[3-chloro-2-(substituted phenyl)-4-oxo-azetidin-1-yl]-biphenyl-4-yl}-7-hydroxy-4-methyl-1H-quinolin-2-one (4a-j). Purity of synthesized compounds was checked by TLC and the structures were elucidated by their IR,1H NMR, Mass and elemental analysis data. The synthesized compounds were screened for anticonvulsant activity.