One-Pot Friedlander Quinoline Synthesis: Scope and Limitations

A highly effective one-pot Friedlander quinoline synthesis from o-nitroarylcarbaldehydes and ketones or aldehydes was developed and the scope and limitations of the method were examined. The o-nitroarylcarbaldehydes were reduced to o-aminoarylcarbaldehydes with iron in the presence of a catalytic amount of aqueous hydrochloric acid; the amino compounds were then condensed in situ with ketones or aldehydes to form mono-or disubstituted quinolines, respectively, in good-to-excellent yields (58-100%).