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Paper | Regular issue | Vol 89, No. 10, 2014, pp.2303-2317
Published online, 29th August, 2014
DOI: 10.3987/COM-14-13070
Efficient Syntheses of Fluorine-Containing Pyrimido[5,4-c]quinolines and Benzo[h][1,6]naphthyridines by Condensation Reactions of 3-Trifluoro-acetylquinolin-4-amine with Aldehydes and Ketones

Etsuji Okada,* Mizuki Hatakenaka, Shiro Nakano, Takushi Sakaemura, Takashi Mori, and Terukazu Terauchi

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


3-Trifluoroacetylquinolin-4-amine reacted easily with various aldehydes in the presence of aqueous ammonia to afford mainly trifluoromethylated pyrimido[5,4-c]quinoline derivatives in moderate to high yields. In contrast, the use of ketones instead of aldehydes under almost the same conditions, mostly gave benzo[h][1,6]naphthyridine derivatives in excellent combined yields.