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2-[5'-CH3(H)-苯并咪唑-2'-亚甲硫基]-5-取代-1,3,4-噁二唑的合成及生长素活性

安悦1*,韩杰1,张婷1,冯辉2,周晓霞1   

  1. (辽宁师范大学1.化学化工学院;2.分析测试中心 大连 116029)
  • 收稿日期:2012-10-12 修回日期:2013-01-04 出版日期:2013-08-10 发布日期:2013-08-10
  • 通讯作者: 安悦，教授; Tel/Fax:0411-84258991; E-mail:anyue_11@163.com; 研究方向：有机合成
  • 基金资助:
    辽宁省教育厅资助项目（2008349）

Synthesis and Biological Activities of 2-{[(5'-Methyl(H)-benzoimidazol-2'-yl]methylthio}-5-substituted-1,3,4-oxadiazole Derivatives

AN Yue1*, HAN Jie1, ZHANG Ting1, FENG Hui2, ZHOU Xiaoxia1   

  1. (1.College of Chemistry and Chemical Engineering;2.Analysis and Inspection Center,
    Liaoning Normal University,Dalian 116029,China)
  • Received:2012-10-12 Revised:2013-01-04 Published:2013-08-10 Online:2013-08-10
  • Contact: Anyue

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1131

被引次数

2

摘要： 以邻苯二胺(或4-甲基邻苯二胺)及一氯乙酸为原料，在酸性条件下，合成2-氯甲基苯并咪唑及2-氯甲基-5-甲基苯并咪唑；以取代羧酸为原料经酯化、肼解、再与CS2在氢氧化钾溶液中反应，合成10种2-巯基-5-取代-1,3,4-噁二唑；将2种2-氯甲基-5-取代苯并咪唑与10种2-巯基-5-取代-1,3,4-噁二唑在氢氧化钠溶液中反应，合成14种2-[5′-CH3（H）-苯并咪唑-2′-亚甲硫基]-5-取代-1,3,4-噁二唑衍生物。 借助红外光谱、核磁共振氢谱和元素分析对化合物结构进行表征。 初步生长素活性测试结果表明，所合成的化合物对小麦芽鞘和绿豆发芽有着不同程度的生长调节作用。

关键词: 苯并咪唑, 噁二唑, 合成, 生长素活性

Abstract: Two kinds of 2-chloromethyl-benzimidazole were synthesized by substituted-o-diaminobenzene and monochloroacetic acid in hydrochloric acid solution. With substituted carboxylic acid as the starting materials, ten kinds of 1,3,4-oxadiazoles were prepared via esterification, hydrazinolysis, followed by reaction with carbon disulfide in potassium hydroxide solution. At last, fourteen new target compounds were synthesized by reacting 5-substituted-1,3,4-oxadiazole-3-thiol with 2-chloromethyl-5-substituted-bezoimidazole in sodium hydroxide solution. The structures of all the compounds were characterized by IR, 1H NMR and elemental analysis. Preliminary biological activity experiments showed that the synthesized compounds had certain effects on the wheat gemma and germination of mung bean.

Key words: benzoimidazole, oxadiazole, synthesis, biological activity

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