A FACILE AND CONVENIENT SYNTHETIC METHOD FOR FLUORINE-CONTAINING DIBENZO[b,h][1,6]NAPHTHYRIDINES, THIOCHROMENO[3,2-c]QUINOLINES, AND CHROMENO[3,2-c]QUINOLINES

Novel fluorine-containing dibenzo[b,h][1,6]naphthyridines (3), thiochromeno[3,2-c]quinolines (5), and chromeno[3,2-c]quinolines (7) were synthesized in moderate to high yields by the trifluoromethanesulfonic acid catalyzed cyclization of N-aryl-3-trifluoroacetyl-4-quinolylamines (2) and aryl 3-trifluoroacetyl-4-quinolyl sulfides (4) and ethers (6), easily prepared by aromatic nucleophilic substitution reactions of N,N-dimethyl-3-trifluoroacetyl-4-quinolylamine (1) with p-substituted anilines, thiophenols, and phenols, respectively.