E. Okada et al., Facile syntheses of fluorine-containing pyrazolo[4,3-h]quinolines and 1H-1,4-diazepino[6,5-h]quinolines, SYNTHESIS-S, (13), 2000, pp. 1822-1824
N,N-Dimethyl-5,7-bis(trifluoroacetyl)-8-quinolylamine underwent an aromatic
nucleophilic N-N exchange reaction with hydrazines followed by cycloconden
sation to afford the corresponding fluorine-containing 1H- and 2H-pyrazolo[
4,3-h]quinolines in excellent yields. This reaction could be extended to th
e synthesis of 1H-1,4-diazepino[6,5-h]quinolines using 1,2-ethylenediamine
and 1,2-phenylenediamines.