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有机化学
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有机化学 ›› 2011, Vol. 31 ›› Issue (03): 374-378. 上一篇    下一篇

研究简报

过渡金属催化下N-取代苯基-苯并噻(噁)唑酮-3-甲酰胺的合成及其生物活性

翁建全*,1，刘幸海1，张国富1，谭成侠1，丁成荣1，欧晓明2   

  1. (1浙江工业大学化学工程与材料学院 杭州 310032)
    (2国家南方农药创制中心湖南基地 长沙 410007)
  • 收稿日期:2010-04-02 修回日期:2010-09-10 发布日期:2010-10-20
  • 通讯作者: 翁建全 E-mail:jqweng@zjut.edu.cn
  • 基金资助:

    国家自然科学基金;浙江省自然科学基金

Transition-Metal-Catalyzed Synthesis and Biological Activities of N-Arylaminocarbonyl-2-benzothiazolinone/benzoxazolone

Weng Jianquan*,1 Liu Xinghai1 Zhang Guofu1 Tan Chengxia1 Ding Chen-grong1 Ou Xiaoming2   

  1. (1 College of Chemical Engineering and Materials Science, Zhejiang University of Technology, Hangzhou 310032)
    (2 Hunan Branch of National Southern Pesticide Research Centre, Changsha 410007)
  • Received:2010-04-02 Revised:2010-09-10 Published:2010-10-20
  • Contact: Jian-Quan Weng E-mail:jqweng@zjut.edu.cn

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被引次数

8 | 3

为了寻找新的含苯并噻(噁)唑稠杂环农药先导化合物, 利用(6-氯)-苯并噻(噁)唑酮与取代苯基异氰酸酯发生偶合反应, 合成了15个N-取代苯基-苯并噻(噁)唑酮-3-甲酰胺化合物3, 并利用1H NMR, IR, MS及元素分析对其结构进行了表征. 初步生物活性试验结果表明, 在试验浓度下部分目标化合物具有一定的杀菌和杀虫活性. 考察了部分过渡金属催化剂对该偶合反应的催化效果, 结果表明在钯催化、温和条件下即可较高产率得到产物.

关键词: 过渡金属催化, 苯并噻(噁)唑酮, 取代苯基异氰酸酯, 合成, 生物活性

In order to find new benzothiazole/benzoxazole lead compounds, 15 N-arylaminocarbonyl-2- benzothiazolinone/benzoxazolone derivatives were synthesized from a coupling reaction of 2-benzothiazolinone/benzoxazolone and aryl isocyanates catalyzed by transition-metal. Their structures were confirmed by 1H NMR, IR, MS techniques and elemental analysis. The preliminary bioassay showed that some of them exhibited certain fungicidal and insecticidal activities. The influence of some transition-metal catalyst on the coupling reaction was studied. The results showed that the corresponding prducts were obtained in high yields in the presence of palladium catalyst under mild reaction conditions.

Key words: transition-metal-catalyzed, 2-benzothiazolinone/benzoxazolone, substituted phenyl isocy-anate, synthesis, biological activity