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2-氰基-3-取代氨基-3-(2-甲基苯基)丙烯酸乙酯的合成和杀菌活性

Synthesis and Fungicidal Activity of Ethyl 2-Cyano-3-substituted Amino-3-(2-methylphenyl)propenoate

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【作者】 王龙根王凤云刁亚梅倪珏萍韦萍

【Author】 WANG, Long-Gena,b WANG, Feng-Yunc DIAO, Ya-Meic NI, Jue-Ping*,c WEI, Pinga (a College of Life Science and Pharmacy, Nanjing University of Technology, Nanjing 210009) (b Central Research Institute of China Chemical Science and Technology, Beijing 100011) (c Jiangsu Branch of National Pesticide Research and Development South Center, Nanjing 210036)

【机构】 南京工业大学制药与生命科学学院国家南方农药创制中心江苏基地南京工业大学制药与生命科学学院 南京210009中化化工科学技术研究总院北京100011南京210036南京210009

【摘要】 2-甲基苯甲酰氯与氰乙酸乙酯反应得到2-氰基-3-羟基-3-(2-甲基苯基)丙烯酸乙酯,经氯化得到2-氰基-3-氯-3-(2-甲基苯基)丙烯酸乙酯,再用三乙胺处理合成了11个2-氰基-3-取代氨基-3-(2-甲基苯基)丙烯酸乙酯类目标化合物.生物活性研究表明这类新化合物具有良好的杀菌活性.

【Abstract】 11 novel Z-ethyl 2-cyano-3-substituted amino-3-(2-methylphenyl)propenoate were synthesized through three steps: the first one involved reaction of ethyl cyanoacetate with 2-methylbenzoylchloride to yield ethyl E-2-cyano-3-hydroxy-3-(2-methylphenyl)propenoate, which then reacted with phosphoroxychlo-ride in the presence of triethylamine to afford a mixture of ethyl E- and Z-3-chloro-2-cyano-3-(2-methyl-phenyl)propenoate, and finally treatment of this mixture with ammomia or primary amines gave the title compounds. Their structures were confirmed by MS and 1H NMR spectra. Biological activity evaluation showed that some of them exhibited fungicidal activities.

【基金】 国家“十五”科技攻关(No.2004BA308A24-1)资助项目.
  • 【文献出处】 有机化学 ,Chinese Journal of Organic Chemistry , 编辑部邮箱 ,2005年10期
  • 【分类号】R914;
  • 【被引频次】23
  • 【下载频次】307
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