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Paper | Special issue | Vol 95, No. 1, 2017, pp.322-341
Published online, 10th November, 2016
DOI: 10.3987/COM-16-S(S)23
Efficient Synthesis of Fluorine-Containing Dibenzo[b,h][1,6]naphthyridines and Thiochromeno[3,2-c]quinolines Using Highly Chemoselective Nucleophilic Substitution Reaction of 4-Dimethylamino-2-methoxy-3-trifluoroacetylquinoline

Etsuji Okada,* Mizuki Hatakenaka, Yoshinori Takezawa, and Keisuke Iwakuni

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

Abstract

Aromatic nucleophilic substitution reaction of N,N-dimethyl-2-methoxy-3-trifluoroacetyl-4-quinolylamine with various nucleophiles (NuH) such as amines, thiols, and alcohols proceeded chemoselectively at the 4-position to give the corresponding Me2N-Nu exchanged products. Novel fluorine-containing 6-methoxydibenzo[b,h][1,6]naphthyridines (11) and 6-methoxythiochromeno[3,2-c]quinolines (12) were synthesized in moderate to high yields by the trifluoromethanesulfonic acid catalyzed cyclization of thus obtained N-aryl-2-methoxy-3-trifluoroacetyl-4-quinolylamines (8) and aryl 2-methoxy-3-trifluoroacetyl-4-quinolyl sulfides (9), respectively.