苯炔参与喹啉衍生物去芳构化反应及抑菌活性研究

Benzyne-Participated Dearomatization of Quinoline Derivatives and Antibacterial Activity of Dearomatized Quinoline Derivatives

以不同取代的Kobayashi苯炔前体和2-乙酰亚甲基喹啉为原料,合成了去芳构化喹啉衍生物,通过^(1)HNMR、^(13) CNMR、HRMS对其结构进行了表征,并对其抑菌活性进行了评价。结果表明,在溶剂为乙腈、氟离子源为CsF、室温反应的最佳条件下,不同取代的Kobayashi苯炔前体与2-乙酰亚甲基喹啉反应均能得到预期目标化合物Ⅲa~Ⅲf,产率为34%~75%;除目标化合物Ⅲe外,其它5种目标化合物均对金黄色葡萄球菌具有较好的抑菌活性。

Taking Kobayashi benzyne precursor with different substitutions and 2-acetylmethylene quinoline as raw materials,we synthesized dearomatized quinoline derivatives,and characterized their structures by ^(1)HNMR,^(13) CNMR,and HRMS.Moreover,we evaluated their antibacterial activity.The results show that the expected target compoundsⅢa-Ⅲf with the yield of 34%-75%can be obtained by the reaction of Kobayashi benzyne precursor with different substitutions and 2-acetylmethylene quinoline under the optimal reaction conditions as follows:acetonitrile is adopted as the solvent,CsF is adopted as the fluoride ion source,and reaction at room temperature.Except for the target compoundⅢe,the other five target compounds show good antibacterial activity against Staphylococcus aureus.