Chin. J. Org. Chem. ›› 2019, Vol. 39 ›› Issue (5): 1417-1423.DOI: 10.6023/cjoc201812006 Previous Articles     Next Articles

Articles

离子液体中钯催化O-甲氧基炔酮肟醚串联环化/溴化反应

李建晓, 林绍, 黄瑞康, 李灿, 杨少容   

  1. 华南理工大学化学与化工学院 广州 510640
  • 收稿日期:2018-12-04 修回日期:2019-01-01 出版日期:2019-05-25 发布日期:2019-01-18
  • 通讯作者: 李建晓, 杨少容 E-mail:cejxli@scut.edu.cn;lisryang@scut.edu.cn
  • 基金资助:

    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)和国家大学生创新创业训练计划(No.201810561075)资助项目.

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

Li Jianxiao, Lin Shao, Huang Ruikang, Li Can, Yang Shaorong   

  1. School of Chemistry and Chemical Engineering, South China University of Technology, Guangzhou 510640
  • Received:2018-12-04 Revised:2019-01-01 Online:2019-05-25 Published:2019-01-18
  • Contact: 10.6023/cjoc201812006 E-mail:cejxli@scut.edu.cn;lisryang@scut.edu.cn
  • Supported by:

    Project supported by the National Natural Science Foundation of China (Nos. 21502055, 21642005), the Fundamental Research Funds for the Central Universities (No. 2018ZD16) and the National Training Program of Innovation and Entrepreneurship for Undergraduates (No. 201810561075).

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.

Key words: ionic liquid, palladium catalysis, 2-alkynone O-methyloxime, 4-bromoisoxazole