FACILE AND CONVENIENT SYNTHESES FOR FLUORINE-CONTAINING PYRAZOLO[4,3-c]QUINOLINES, ISOXAZOLOQUINOLINES, AND 1,4-DIAZEPINO[6,5-c]QUINOLINES

N,N-Dimethyl-3-trifluoroacetyl-4-quinolylamine underwent an aromatic nucleophilic N-N exchange reaction with hydrazines followed by cyclocondensation to afford the corresponding novel fluorine-containing 1H- and 2H-pyrazolo[4,3-c]quinolines in good to high yields. This reaction could be extended to the synthesis of novel CF3-containing isoxazoloquinolines using hydroxylamine. Furthermore, the use of 1,2-ethylenediamine and 1,2-phenylenediamines gave the corresponding fluorine-containing 1,4-diazepino[6,5-c]quinoline derivatives in high yields.