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Communication | Special issue | Vol 93, No. 2, 2016, pp.474-481
Published online, 3rd December, 2015
DOI: 10.3987/COM-15-S(T)54
Unexpected Highly Chemoselective Nucleophilic Substitution Reaction of 4-Dimethylamino-2-methoxy-3-trifluoroacetylquinoline with Various Nucleophiles

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 4-dimethyl-amino-2-methoxy-3-trifluoroacetylquinoline with various nucleophiles (NuH) such as amines, thiols, and alcohols proceeded chemoselectively to give the corresponding Me2N-Nu exchanged products, 2-methoxy-3-trifluoroacetyl-4-quinolylamines, sulfides, and ethers without any formation of MeO-Nu exchanged products in spite of the common knowledge that alkoxy group is the better leaving group than amino group.