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Paper | Special issue | Vol 82, No. 1, 2010, pp.803-812
Published online, 29th July, 2010
DOI: 10.3987/COM-10-S(E)71
A Facile Synthesis of Fluorine-Containing 1,7-Phenanthrolines by the Cyclization of N-Propargyl-6,8-bis(trifluoroacetyl)quinolin-5-amine with Various Active Methylene Compounds

Dai Shibata, Ayaka Sakai, Mizuki Hatakenaka, Shohei Saikawa, Yasuhiro Kamitori, Maurice Médebielle, and Etsuji Okada*

*Department of Chemical Science and Engineering, Graduate School of Engineering, Kobe University, 1-1 Rokkodai-cho, Nada-ku, Kobe 657-8501, Japan

Abstract

The reaction of N-propargyl-6,8-bis(trifluoroacetyl)quinolin-5-amine (1) with various active methylene compounds gave the novel fluorine-containing 1,7-phenanthroline derivatives (3). Furthermore, changing the electron-withdrawing groups on active methylene compounds induced interesting alternation of the reaction site wherein the enolate anions attack first and led to construction of the different nitrogen-containing heterocyclic systems, 1,7-phenanthrolinone (4) and 1,4-dihydro-1,7-phenanthroline (5).