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Chin. J. Org. Chem. ›› 2005, Vol. 25 ›› Issue (10): 1254-1258. Previous Articles     Next Articles

Reports

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

王龙根1,2，王凤云3，刁亚梅3，倪珏萍*,3，韦萍1   

  1. (1南京工业大学制药与生命科学学院 南京 210009)
    (2中化化工科学技术研究总院 北京 100011)
    (3国家南方农药创制中心江苏基地 南京 210036)
  • 收稿日期:2004-06-25 修回日期:2005-06-08 发布日期:2005-10-08
  • 通讯作者: 倪珏萍

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

WANG Long-Gen1,2,WANG Feng-Yun3,DIAO Ya-Mei3,NI Jue-Ping*,3 WEI Ping1   

  1. (1 College of Life Science and Pharmacy, Nanjing University of Technology, Nanjing 210009)
    (2 Central Research Institute of China Chemical Science and Technology, Beijing 100011)
    (3 Jiangsu Branch of National Pesticide Research and Development South Center, Nanjing 210036)
  • Received:2004-06-25 Revised:2005-06-08 Published:2005-10-08
  • Contact: NI Jue-Ping

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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 phosphoroxychloride in the presence of triethylamine to afford a mixture of ethyl E- and Z-3-chloro-2-cyano-3-(2-methylphenyl)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.

Key words: ethyl 2-cyano-3-substituted amino-3-(2-methylphenyl)propenoate, synthesis, cyanopropenoate, fungicidal activity