微波辅助下高效合成功能性6-芳基水杨酸类衍生物（英文）  

An Efficient Synthesis of Functionalized 6-Arylsubstituted Salicylates via Microwave Irradiation

作　　者：曲仁渝 陈念[1] 刘玉超[1] 陈琼[1] 杨光富 

机构地区：[1]华中师范大学化学学院农药与化学生物学教育部重点实验室,武汉430079

出　　处：《有机化学》2017年第5期1266-1272,共7页Chinese Journal of Organic Chemistry

基　　金：supported by the Special Fund for Agroscientific Research in the Public Interest(No.201203022);the National Key Technologies R&D Program(No.2014BAD23B01);the National Natural Science Foundation of China(No.21372093)~~

摘　　要：功能化的6-芳基水杨酸片段广泛地存在于各种天然产物以及活性分子中.在基于杂草抗性的分子设计中,6-芳基取代的水杨酸衍生物作为反抗性乙酰羟酸合成酶抑制剂的关键药效团发挥着至关重要的作用.在前期工作中,探索了两种策略可以合成6-芳基取代水杨酸片段,但不能有效地实现在6-芳基水杨酸片段母核结构中的底物多样化.因此,通过微波辅助的Suzuki偶联反应,成功合成了多取代的6-芳基水杨酸片段.这一方法具有反应时间短、反应收率高等优点,并且实现了底物多样化,为后期合成具有反抗性乙酰羟酸合成酶抑制剂奠定了基础.Functionalized 6-arylsalicylate substructures occur in a variety of pharmacologically relevant natural products and bioactive compounds. Especially 6-arylsubstituted salicylates, as a key pharmacophore of anti-resistant acetohydroxyacid syn- thase （AHAS） inhibitors have played a lead role in combatting the weed-resistance issues. Previously, we have explored two new methods to synthesize position-6 aryl substituted salicylic acid fragment. However, these two methods failed to introduce various substituents into salicylic acid. Here an efficient method for the synthesis of 6-substituted salicylates is described via a microwave-promoted Suzuki cross-coupling. Due to the obvious advantages of this method, such as a wide range of substrates, smooth and rapid reaction and moderate to excellent yields, this protocol could be utilized to synthesize more anti-resistant AHAS inhibitors.

关 键 词：功能化6-芳基水杨酸 Suzuki交叉偶联反应 微波辐射 电子效应 

分 类 号：TQ460.1[化学工程—制药化工]