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有机化学
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有机化学 ›› 2011, Vol. 31 ›› Issue (08): 1208-1212. 上一篇    下一篇

研究论文

2-氨基(芳氧基)-3-对甲基苯基噻吩并[3,2:5,6]吡啶并[4,3-d]嘧啶-4(3H)- 酮的合成和生物活性

刘建超，贺红武*，陈荷莲   

  1. (华中师范大学化学学院 农药与化学生物学教育部重点实验室 武汉 430079)
  • 收稿日期:2010-12-08 修回日期:2011-01-29 发布日期:2011-03-17
  • 通讯作者: 刘建超 E-mail:liujc@mail.ccnu.edu.cn

Synthesis and Fungicidal Activities of 2-(Amino/acetoxy)-3- (4-methylphenyl)-thieno[3,2:5,6]pyrido[4,3-d]- pyrimidin-4(3H)-one Derivatives

LIU Jian-Chao, HE Hong-Wu, CHEN He-Lian   

  1. (Key Laboratory of Pesticide and Chemical Biology of Ministry of Education, College of Chemistry, Central China Normal University, Wuhan 430079)
  • Received:2010-12-08 Revised:2011-01-29 Published:2011-03-17
  • Contact: JianChao Liu E-mail:liujc@mail.ccnu.edu.cn

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用邻氨基噻吩腈与乙酰乙酸甲酯为原料, 利用串联Aza-Wittig法合成了9个未见文献报道的噻吩并吡啶并嘧啶类化合物, 通过IR, 1H NMR, EI-MS, 元素分析等方法对所合成的化合物进行了结构表征, 并初步测定了所合成化合物的杀菌活性. 生测结果表明: 此类化合物对棉花枯萎(Fusarium oxysporium)、水稻纹枯(Rhizoctonia solani)、小麦赤霉(Gibberella zeae)、苹果轮纹菌(Dothiorella gregaria)、棉花炭疽菌(Colletotrichum gossypii)等5种菌均有一定的抑制活性.其中对苹果轮纹菌抑制活性最好, 在浓度为5.0×10－5 g/mL时抑制率为31.80%～82.84%.

关键词: 乙酰乙酸甲酯, Aza-Wittig法, 噻吩并吡啶, 吡啶并嘧啶, 杀菌活性

A novel facile synthetic method for thienopyridine derivatives was proposed via the reaction of 2-amino-thiophenes with acetoacetic ester and tin tetrachloride under heating. A series of new 2-(amino/ acetoxy)-3-(4-methylphenyl)-thieno[3,2:5,6]pyrido[4,3-d]pyrimidin-4(3H)-one derivatives had been designed and synthesized via an aza-Wittig reaction and structually confirmed by IR, 1H NMR, EI-MS techniques, and elemental analysis. Their biological activities were also re-searched and many of them showed fungicidal activities against Fusarium oxysporium, Rhizoctonia solani, Gibberella zeae, Dothiorella gregaria and Colletotrichum gossypii to some extent. They exhibited 31.80%～82.84% inhibition against Dothiorella gregaria at 5.0×10－5 g/mL.

Key words: acetoacetic ester, aza-Wittig reaction, thienopyridine, pyrido[4,3-d]pyrimidine, fungicidal activity