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Synthesis 2009(18): 3039-3046  
DOI: 10.1055/s-0029-1216893
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

A Facile Synthetic Method for Fluorine-Containing 1,7-Phenanthrolines: Pyridine-Ring Formation Reaction of N-Propargyl-6,8-bis(trifluoroacetyl)quinolin-5-amine with Various Nucleophiles

Dai Shibataa, Etsuji Okada*b, Mamoru Hinoshitab, Maurice Médebiellec
a Graduate School of Science and Technology, Kobe University, Rokkodai-cho, Nada-ku, Kobe 657-8501, Japan
b Department of Chemical Science and Engineering, Graduate School of Engineering, Kobe University, Rokkodai-cho, Nada-ku, Kobe 657-8501, Japan
Fax: +81(78)8036194; e-Mail: okaetsu@kobe-u.ac.jp;
c Université de Lyon, Institut de Chimie et Biochimie Moléculaires et Supramoléculaires (ICBMS), Université Claude Bernard Lyon 1 (UCBL), Laboratoire de Synthèse de Biomolécules (LSB), UMR 5246 CNRS-UCBL-INSA Lyon-CPE Lyon, 43 Bd du 11 Novembre 1918, 69622 Villeurbanne, France
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Publication History

Received 25 March 2009
Publication Date:
10 July 2009 (online)

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Abstract

Novel fluorine-containing 1,7-phenanthrolines with a variety of substituents at the 3-position were easily synthesized in moderate to high yields by the pyridine-ring formation reaction of N-propargyl-6,8-bis(trifluoroacetyl)quinolin-5-amine with various amines, thiols, alcohols, and phenols.

Key words

1,7-phenanthrolines - fluorine - pyridine-ring formation - propargylamines - 5-quinolines

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