Conversion of indones to quinoline and isoquinoline derivatives—IV : Schmidt reaction with 2-( o-carboxyphenyl)3-phenylindone and with 2-( o-carbomethoxyphenyl)-3-phenylindone

Abstract

The Schmidt reaction with 2-( o-carboxyphenyl)3-phenylindone (VI) in a mixture of sulphuric and acetic acid affords 12-phenyl-5 H-[2]benzopyrano[3.4- b]quinoline-5-one (VII) as the main product. The methyl ester of V, which is almost unreactive towards hydrazoic acid in acetic-sulphuric acid solution, is converted mainly into 2-phenyl-3-( o-carbomethoxyphenyl)4--hydroxyquinoline (XVI) when the reaction is carried out in concentrated sulphuric acid solution.