新型2-(芳氨基乙基氨基)苯甲醇的合成及其杀菌活性

doi:10.11944/j.issn.1000-0518.20176.03.160236

摘要/Abstract

摘要：

2-氨基苯甲醇及其衍生物是一类很重要的具有双官能团的化合物,在有机化学和药物合成中具有广泛的用途。本文主要提供了一种简单、有效合成2-(芳氨基乙基氨基)苯甲醇类化合物的方法,同时测定了目标化合物的杀菌活性。溴乙酰芳胺与2-氨基苯甲醇经N-烷基化反应生成2-[(2-羟甲基苯基)氨基]乙酰芳胺类化合物3,然后经LiAlH₄还原生成了一系列结构新颖的2-(芳氨基乙基氨基)苯甲醇类化合物5a~5i,产率为76%~95%。用IR、¹H NMR、¹³C NMR和元素分析等对产物结构进行了表征。目标化合物的杀菌活性结果表明,在测试浓度下,大部分显示中等至良好的活性,化合物5e对辣椒疫霉病菌的抑制活性达73.0%。

关键词: (芳氨基乙基氨基)苯甲醇, 烷基化, 合成, 杀菌活性

Abstract:

2-Aminobenzyl alcohol and its derivatives are a kind of important bifunctional compounds, and has found wide application in organic chemistry and drug synthesis. An efficient and simple method for synthesis of 2-(arylaminoethylamino)benzyl alcohols was described and the fungicidal activities of the target compounds were evaluated in this paper. N-alkylation of 2-aminobenzyl alcohol with bromoacetyl aryl amines produced 2-[(2-hydroxymethylphenyl)amino] acetyl aryl amines 3a~3i, which were reduced by LiAlH₄ giving a series of novel 2-(arylaminoethylamino)benzyl alcohols 5a~5i in 76%~95% yields. All the structures of the target compounds were characterized by the infrared spectroscopy(IR), proton nuclear magnetic resonance spectroscopy(¹H NMR), ¹³C NMR and elemental analysis. Most of compounds show moderate to good fungicidal activities under the testing concentration. Compound 5e shows 73% activity of against Phytophythora capsici.

Key words: (arylaminoethylamino)benzyl alcohol, alkylation, synthesis, fungicidal activity

唐子龙, 谭经照, 蔡兰琼, 李新兴, 刘万强. 新型2-(芳氨基乙基氨基)苯甲醇的合成及其杀菌活性[J]. 应用化学, 2017, 34(3): 345-353.

TANG Zilong, TAN Jingzhao, CAI Lanqiong, LI Xinxing, LIU Wanqiang. Synthesis and Fungicidal Activity of Novel 2-(Arylaminoethylamino)benzyl Alcohols[J]. Chinese Journal of Applied Chemistry, 2017, 34(3): 345-353.

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