This paper firstly describes the synthesis of a series of (Z)-4-((3-chloro-4-fluorophenyl)amino)-1,1,1-trifluorobut-3-en-2-ones (3a–f) as well as 1-(1-((3-chloro-4-fluorophenyl)amino)-3,4-dihydronaphthalen-2-yl)-2,2,2-trifluoroethanone (3g), from the O,N-exchange reaction of some 4-methoxy-4-alkyl(aryl)-1,1,1-trifluoroalk-3-en-2-ones (1) with 3-chloro-4-fluoroaniline (2), at 70–90% yields. Subsequently, in concentrated sulfuric acid, the enaminoketones 3 underwent a successful and regioselective intramolecular cyclocondensation reaction, which furnished a novel series of 2-alkyl(aryl)-7-chloro-6-fluoro-4-(trifluoromethyl)-quinolines (4) at 70–85% yields. To demonstrate synthetic applicability through the Sonogashira coupling reaction for obtaining quinolines with potential antimicrobial activity, the synthesis of a novel series of 2-alkyl(aryl)-6-fluoro-7-(phenylethynyl)-4-(trifluoromethyl)-quinolines (5) was performed, using quinolines 4 and phenylacetylene, via a regioselective Sonogashira coupling reaction (25–50% yield). Unfortunately, the new series of heterocycles 4 and 5 did not produce significant results against bacteria and fungi at the concentrations of 80–0.31 μg/mL.

本文首先描述了一系列（Z）-4-（（3-氯-4-氟苯基）氨基）-1,1,1-三氟丁-3-烯-2-酮（3a–f）的合成以及O，N交换反应中的1-（1-（（3-氯-4-氟苯基）氨基）-3,4-二氢萘-2-基）-2,2,2-三氟乙酮（3g）用70-90％的产率将一些4-甲氧基-4-烷基（芳基）-1,1,1-三氟烷基-3-烯-2-酮（1）与3-氯-4-氟苯胺（2）结合使用。随后，在浓硫酸中，烯氨基酮3进行了成功的区域选择性分子内环缩合反应，从而提供了一系列新颖的2-烷基（芳基）-7-氯-6-氟-4-（三氟甲基）-喹啉（4）以70-85％的收益率。为了通过Sonogashira偶联反应证明具有潜在抗菌活性的喹啉的合成适用性，合成了一系列新型的2-烷基（芳基）-6-氟-7-（苯基乙炔基）-4-（三氟甲基）-喹啉（5）是通过喹啉4和苯乙炔通过区域选择性Sonogashira偶联反应（25-50％的收率）进行的。不幸的是，在浓度为80–0.31μg/ mL的情况下，新系列的杂环4和5并未对细菌和真菌产生显着结果。