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Short Paper | Regular issue | Vol 94, No. 1, 2017, pp.102-116
Published online, 9th December, 2016
DOI: 10.3987/COM-16-13595
Facile and Convenient Syntheses of Fluorine-Containing Pyrimido[5,4-c]quinolines and Benzo[h][1,6]naphthyridines by Condensation Reaction of 2-Methoxy-3-trifluoroacetyl-4-quinolylamine with Aldehydes and Ketones

Mizuki Hatakenaka 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

2-Methoxy-3-trifluoroacetyl-4-quinolylamine 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 in the presence of pyrrolidine, exclusively gave benzo[h][1,6]naphthyridine derivatives in good to excellent yields.