Facile Syntheses of Fluorine-Containing Pyrazol[4,3-h]quinolines and 1H-1,4-Diazepino[6,5-h]quinolines

Etsuji Okada; Norikado Tsukushi; Naofumi Shimomura

doi:10.1055/s-2000-8234

Synthesis 2000; 2000(13): 1822-1824
DOI: 10.1055/s-2000-8234

short paper

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Facile Syntheses of Fluorine-Containing Pyrazol[4,3-h]quinolines and 1H-1,4-Diazepino[6,5-h]quinolines

Etsuji Okada^* , Norikado Tsukushi, Naofumi Shimomura

^*Department of Chemical Science and Engineering, Faculty of Engineering, Kobe University, Rokkodai-cho, Nada-ku, Kobe 657-8501, Japan; Fax +81(78)803-6206; E-mail: okada@cx.kobe-u.ac.jp

Abstract

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N,N-Dimethyl-5,7-bis(trifluoroacetyl)-8-quinolylamine underwent an aromatic nucleophilic N - N exchange reaction with hydrazines followed by cyclocondensation to afford the corresponding fluorine-containing 1H- and 2H-pyrazolo[4,3-h]quinolines in excellent yields. This reaction could be extended to the synthesis of 1H-1,4-diazepino[6,5-h]quinolines using 1,2-ethylenediamine and 1,2-phenyldiamines.

nucleophilic aromatic substitutions - fluorine compounds - quinolylamines - pyrazoloquinolines - diazepinoquinolines

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