有机化学 ›› 2017, Vol. 37 ›› Issue (9): 2399-2408.DOI: 10.6023/cjoc201702026 上一篇    下一篇

研究论文

3,4-二芳基-5-芳氧甲基异噁唑的合成

蒋海芳a, 张敏a, 张丽a, 陈雅丽a, 朱宁a, 宋力平a,b, 邓红梅c   

  1. a 上海大学理学院化学系 上海 200444;
    b 中国科学院有机氟化学重点实验室 上海 200032;
    c 上海大学微结构重点实验室 上海 200444
  • 收稿日期:2017-02-20 修回日期:2017-04-07 出版日期:2017-09-25 发布日期:2017-05-25
  • 通讯作者: 张敏, 宋力平 E-mail:mzhang@shu.edu.cn;lpsong@shu.edu.cn
  • 基金资助:

    国家自然科学基金(No.21272153)资助项目.

Synthesis of 3,4-Diaryl-5-aryloxymethyl Isoxazole Derivatives

Jiang Haifanga, Zhang Mina, Zhang Lia, Chen Yalia, Zhu Ninga, Song Lipinga,b, Deng Hongmeic   

  1. a Department of Chemistry, School of Science, Shanghai University, Shanghai 200444;
    b Key Laboratory of Organofluorine Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032;
    c Laboratory for Microstructures, Shanghai University, Shanghai 200444
  • Received:2017-02-20 Revised:2017-04-07 Online:2017-09-25 Published:2017-05-25
  • Contact: 10.6023/cjoc201702026 E-mail:mzhang@shu.edu.cn;lpsong@shu.edu.cn
  • Supported by:

    Project supported by the National Natural Science Foundation of China (No. 21272153).

由于异噁唑衍生物具有广泛的除草、杀虫和药物活性,其合成方法近年来一直引起关注.以3-芳基-5-溴甲基异噁唑为原料,经溴代、醚化、Suzuki偶联反应合成了一系列3,4-二取代芳基-5-芳氧甲基异噁唑化合物,初步的生物活性测试结果显示,部分化合物对粘虫显示出一定的杀虫活性.

关键词: 异噁唑衍生物, 溴代, 醚化, Suzuki偶联反应

Due to isoxazole derivatives possess a wide range of herbicidal, insecticidal and pharmacological activitives, the synthetic methodologies for preparation of isoxazole derivatives have drawn much attention in recent years. Herein, 3,4-diaryl-5-aryloxymethyl isoxazole derivatives were effectively synthesized from 3-aryl-5-(bromomethyl)isoxazole via consecutive bromination, etherification, followed by Suzuki coupling reaction catalyzed by Pd(PPh3)2Cl2. Preliminary bioassay data showed that some of the title compounds exhibited certain insecticidal activities against Oriental armyworm.

Key words: isoxazole derivatives, bromination, etherification, suzuki coupling reaction