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Synthesis 2000; 2000(2): 237-242
DOI: 10.1055/s-2000-6243
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Aromatic Nucleophilic N-N, N-S and N-O Exchange Reactions: Efficient Synthesis of 5,7-Bis(trifluoroacetyl)-8-quinolylamines, Sulfides and Ethers

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) 8 03 62 06; E-mail: okada@appchem.chme.kobe-u.ac.jp
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Publication Date:
31 December 2000 (online)

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Various 5,7-bis(trifluoroacetyl)-8-quinolylamines, sulfides and ethers were synthesized in excellent yields by aromatic nucleophilic N-N, N-S and N-O exchange reactions of N,N-dimethyl-5,7-bis(trifluoroacetyl)-8-quinolylamine with amines, thiols and alcohols. Base-catalyzed cyclization of the resulting benzyl 8-quinolyl sulfide and subsequent dehydration gave fluorine-containing thieno[3,2-h]quinolines in high yields.

nucleophilic aromatic substitutions - fluorine compounds - quinolylamines - quinolyl sulfides - quinolyl ethers