研究论文

具有5-芳氧甲基(芳胺甲基)链接的3-芳基异噁唑衍生物的合成及其生物活性初探

  • 徐姗姗 ,
  • 张敏 ,
  • 张丽 ,
  • 蒋海芳 ,
  • 朱宁 ,
  • 宋力平 ,
  • 邓红梅
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  • a 上海大学理学院化学系 上海 200444;
    b 中国科学院上海有机化学研究所 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: 2015-05-28

  修回日期: 2015-06-22

  网络出版日期: 2015-08-25

基金资助

国家自然科学基金(Nos. 21272153, 21072128)资助项目.

Synthesis of Novel 3-Aryl-isoxazoles Bearing 5-Aryloxymethyl or 5-Arylaminomethyl Linkage System as Potential Pesticides

  • Xu Shanshan ,
  • Zhang Min ,
  • Zhang Li ,
  • Jiang Haifang ,
  • Zhu Ning ,
  • Song Liping ,
  • Deng Hongmei
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  • 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 date: 2015-05-28

  Revised date: 2015-06-22

  Online published: 2015-08-25

Supported by

Project supported by the National Natural Science Foundation of China (Nos. 21272153, 21072128).

摘要

以3-芳基-5-溴甲基异噁唑(1)为原料, 与相应的酚或胺类发生亲核取代反应, 合成了一系列未见报道的3-芳基-5-芳氧甲基异噁唑衍生物和3-芳基-5-芳胺甲基(或苄胺甲基)异噁唑衍生物. 化合物结构均经过1H NMR, IR, MS, HRMS和元素分析鉴定. 通过合成的3-芳基-5-芳氧甲基异噁唑(3)对Aphis crassivora的致死率来评价了该系列化合物的生物活性, 其中3-(2-氰基苯基)-5-(2-氯苯氧甲基)异噁唑(3p)表现出了较好的生物活性.

本文引用格式

徐姗姗 , 张敏 , 张丽 , 蒋海芳 , 朱宁 , 宋力平 , 邓红梅 . 具有5-芳氧甲基(芳胺甲基)链接的3-芳基异噁唑衍生物的合成及其生物活性初探[J]. 有机化学, 2015 , 35(12) : 2595 -2603 . DOI: 10.6023/cjoc201505047

Abstract

A new class of 3-aryl-5-aryloxymethylisoxazole derivatives and 3-aryl-5-arylaminomethyl (or 5-benzylamino- methyl) isoxazole derivatives were designed and efficiently synthesized by nucleophilic substitution reaction of 3-aryl-5-bro- momethylisoxazole (1) with the corresponding phenols or anilines (or benzyl amines), respectively. All of the target compounds were characterized by 1H NMR, IR, MS and elemental analysis. Besides, a biological activity study was performed to evaluate the mortality of 3-aryl-5-aryloxy-methylisoxazoles (3) towards Aphis crassivora. Particularly, 3-(2-cyanophenyl)-5- (2-chrolophenoxymethyl)isoxazole (3p) demonstrated a moderate biological activity.

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