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有机化学
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有机化学 ›› 2008, Vol. 28 ›› Issue (10): 1785-1791. 上一篇    下一篇

研究简报

4(3H)-喹唑啉酮类Schiff碱的合成与抗烟草花叶病毒活性

高兴文; 蔡学建; 严 凯; 高丽丽;
王和英 ; 陈 卓; 宋宝安*
  

  1. (贵州大学精细化工研究开发中心 教育部绿色农药与农业生物工程重点实验室 贵阳 550025)
  • 收稿日期:2007-10-25 修回日期:2008-02-14 发布日期:2008-10-20
  • 通讯作者: 宋宝安

Synthesis and Anti-tobacco Mosaic Virus Activity of 4(3H)-Quinazolinone Schiff Base

GAO, Xing-Wen; CAI, Xue-Jian; YAN, Kai; GAO, Li-Li ;WANG, He-Ying ; CHEN, Zhuo ; SONG, Bao-An*
  

  1. (Key Laboratory of Green Pesticide and Agricultural Bioengineering, Ministry of Education, Research and
    Development Center of Fine Chemicals, Guizhou University, Guiyang 550025)
  • Received:2007-10-25 Revised:2008-02-14 Published:2008-10-20
  • Contact: SONG, Bao-An

PDF

1478

被引次数

93

采用邻氨基苯甲酸经醋酐酰化闭环得2-甲基苯并噁嗪-4-酮, 水合肼回流合成2-甲基-3-氨基-4(3H)-喹唑啉酮, 在无水乙醇中与芳醛反应得4(3H)-喹唑啉酮类Schiff碱. 经元素分析, IR, 1H NMR, 13C NMR对所合成的化合物进行了结构确认和表征. 初步生物活性测试表明, 化合物3t具有较高的抗烟草花叶病毒活性.

关键词: 4(3H)-喹唑啉酮, Schiff碱, 抗烟草花叶病毒活性, 合成

Starting from anthranilic acid, 4(3H)-quinazolinone Schiff base derivatives 3 were synthesized by a three-step process. Cyclization reaction of anthranilic acid with acetic anhydride afforded 2-methyl-3,1- benzoxazin-4-one 1, in which was then converted into the intermediate 2 by hydrazination reaction. Con-densation reaction of substituted benzaldehyde with 3-amino-2-methyl-4(3H)-quinazolinone 2 in a refluxing ethanol gave the 4(3H)-quinazolinone Schiff base. Their structures of 3 were established by elemental analysis, IR, 1H NMR and 13C NMR spectra. The bioassay of title compound 3t showed that it had good anti-tobacco mosaic virus activity.

Key words: Schiff base moiety, 4(3H)-quinazolinone, synthesis, anti-TMV activity