引用本文:
安悦, 韩杰, 张婷, 冯辉, 周晓霞. 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[J]. 应用化学,
2013, 30(8): 872-877.
doi:
10.3724/SP.J.1095.2013.20458
Citation: AN Yue, HAN Jie, ZHANG Ting, FENG Hui, ZHOU Xiaoxia. Synthesis and Biological Activities of 2-{[5'-Methyl(H) benzoimidazol-2'-yl]methylthio}-5-substituted-1,3,4-oxadiazole Derivatives[J]. Chinese Journal of Applied Chemistry, 2013, 30(8): 872-877. doi: 10.3724/SP.J.1095.2013.20458
Citation: AN Yue, HAN Jie, ZHANG Ting, FENG Hui, ZHOU Xiaoxia. Synthesis and Biological Activities of 2-{[5'-Methyl(H) benzoimidazol-2'-yl]methylthio}-5-substituted-1,3,4-oxadiazole Derivatives[J]. Chinese Journal of Applied Chemistry, 2013, 30(8): 872-877. doi: 10.3724/SP.J.1095.2013.20458
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
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。
English
Synthesis and Biological Activities of 2-{[5'-Methyl(H) benzoimidazol-2'-yl]methylthio}-5-substituted-1,3,4-oxadiazole Derivatives
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.
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Key words:
- benzoimidazole
- / oxadiazole
- / synthesis
- / biological activity
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