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

作者：Ota Norio^*; Hatakenaka Mizuki; Ashida Takuro; Okada Etsuji

来源：Heterocycles, 2013, 87(12): 2641-2649.

DOI：10.3987/COM-13-12849

• Chloroquine Analogue
• 7-Chloro-4-dimethylaminoquinoline
• Antimalarial Activity
• Nucleophilic Substitution
• Tnfluoroacetylation

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.

• 出版日期2013-12-1