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Paper | Special issue | Vol 90, No. 2, 2015, pp.1072-1081
Published online, 5th August, 2014
DOI: 10.3987/COM-14-S(K)76
Facile and Convenient Syntheses for Fluorine-Containing Pyrazolo[4,3-c]quinolines, Isoxazoloquinolines, and 1,4-Diazepino[6,5-c]quinolines

Etsuji Okada,* Mizuki Hatakenaka, and Takushi Sakaemura

*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-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.