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Short Paper | Regular issue | Vol 92, No. 5, 2016, pp.936-943
Published online, 4th March, 2016
DOI: 10.3987/COM-16-13420
Facile Syntheses of Fluorine-Containing 4-Methoxypyrazolo[4,3-c]quinolines and 6-Methoxy-1,4-diazepino[6,5-c]quinolines

Mizuki Hatakenaka, Satoru Adachi, and Etsuji Okada*

*Department of Chemical Science and Engineering, Graduate School of Engineering, Kobe University, 1-1 Rokkodai-cho, Nada-ku, Kobe 657-8501, Japan


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