离子液体中钯催化O-甲氧基炔酮肟醚串联环化/溴化反应  

Palladium-Catalyzed Cascade Cyclization/Bromination of 2-Alkynone O-Methyl Oximes in Ionic Liquid

作　　者：李建晓 林绍 黄瑞康 李灿 杨少容[1] Li Jianxiao;Lin Shao;Huang Ruikang;Li Can;Yang Shaorong(School of Chemistry and Chemical Engineering, South China University of Technology, Guangzhou 510640)

机构地区：[1]华南理工大学化学与化工学院

出　　处：《有机化学》2019年第5期1417-1423,共7页Chinese Journal of Organic Chemistry

基　　金：国家自然科学基金(Nos.21502055,21642005);华南理工大学中央高校基本科研业务费重点项目(No.2018ZD16);国家大学生创新创业训练计划(No.201810561075)资助项目~~

摘　　要：在离子液体[Cpmim]Cl中,利用O-甲氧基炔酮肟醚为反应底物,以5mol% Pd(TFA)2为催化剂,2equiv.CuBr2为溴源,以中等至优良产率(68%~90%)合成了系列4-溴代异噁唑衍生物,其结构均经1H NMR,13C NMR及HRMS确证.该反应具有产率高、底物适用范围广、原子经济性高等优点.此外,生成的产物通过进一步的修饰与转化可以衍生为结构复杂的、具有潜在生物活性的异噁唑活性分子.An efficient palladium-catalyzed protocol for the synthesis of 4-bromoisoxazoles derivatives in moderate to good yields from readily available O-methyl oximes in basic ionic liquid has been developed. Their structures were confirmed by 1H NMR, 13C NMR and HRMS. This cascade cyclization/bromination process provides a novel route for directly accessing 4-bromoisoxazole in good to excellent yields and good functional group tolerance with high atom efficiency. Notably, the current methodology could also be conveniently applied to the synthesis of isoxazoles naturally occurring biologically active frameworks.

关 键 词：离子液体 钯催化 O-甲氧基炔酮肟醚 4-溴代异噁唑 

分 类 号：O621.251[理学—有机化学]