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Synthesis 2011(17): 2754-2760  
DOI: 10.1055/s-0030-1260133
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Facile and Convenient Syntheses of Fluorine-Containing Pyrido[2,3-h]-quinazolines and 1,7-Phenanthrolines by Condensation Reactions of 6,8-Bis(trifluoroacetyl)quinolin-5-amine with Carbonyl Compounds

Mamoru Hinoshitaa, Dai Shibatab, Mizuki Hatakenakaa, Etsuji Okada*a
a 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;
b Graduate School of Science and Technology, Kobe University, Rokkodai-cho, Nada-ku, Kobe 657-8501, Japan
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Publikationsverlauf

Received 21 April 2011
Publikationsdatum:
21. Juli 2011 (online)

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Abstract

6,8-Bis(trifluoroacetyl)quinolin-5-amine reacted easily with various aldehydes in the presence of aqueous ammonia to afford trifluoromethylated pyrido[2,3-h]quinazoline derivatives and 1,7-phenanthroline derivatives in good to excellent yields. Under almost the same conditions, the use of ketones instead of aldehydes gave 1,7-phenanthroline derivatives selectively, except in the case of cyclohexanone.

Key words

pyrido[2,3-h]quinazolines - 1,7-phenanthrolines - fluorine - condensation reaction - quinolin-5-amines

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