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Short Paper | Regular issue | Vol 87, No. 12, 2013, pp.2641-2649
Published online, 30th October, 2013
DOI: 10.3987/COM-13-12849
A Versatile Method for the Synthesis of Fluorine-Containing Chloroquine Analogues Starting from 7-Chloro-4-(N,N-dimethylamino)quinoline Using Nucleophilic N-N, N-S, and N-O Exchange Reactions

Norio Ota, Mizuki Hatakenaka, Takuro Ashida, 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

A new synthetic method was developed to access fluorine-containing chloroquine analogues which have unique potentials contributing to the discovery of novel anti-microorganisms. (7-Chloro-3-trifluoroacetylquinolin-4-yl)amines (7), thiols (8), and ethers (9) were easily synthesized in high yields by the trifluoroacetylation of 7-chloro-4-(N,N-dimethylamino)quinoline (6) with 1-trifluoroacetyl-4-dimethylaminopyridinium trifluoroacetate followed by the nucleophilic N-N, N-S, and N-O exchange reactions.