| 1-取代-1H-1,2,3-三唑-4-甲酰胺类化合物的设计合成与生物活性 |
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| 引用本文： | 王振军,刘斌,李永红,赵卫光.1-取代-1H-1,2,3-三唑-4-甲酰胺类化合物的设计合成与生物活性[J].有机化学,2011,31(3). |
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| 作者姓名： | 王振军 刘斌 李永红 赵卫光 |
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| 作者单位： | 南开大学元素有机化学国家重点实验室,农药国家工程中心,天津,300071 |
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| 基金项目： | 国家自然科学基金，"973" |
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| 摘 要： | 以吡唑酰胺类杀菌剂为模板,应用"生物等排原理"设计了1,2,3-三唑甲酰胺类具有等排结构的化合物,从丙炔酸出发合成内炔酰胺后,利用Cu(I)催化的1,3-偶极环加成反应,使其与叠氮化合物反应,快速合成了17个结构新颖的1-取代-1H-1,2,3-三唑-4-甲酰胺类化合物.当使用Cu/C催化时,中间体N-(3,4-二甲氧基苯基乙基)丙炔酰胺(4a)与2,2,2-三氟乙基叠氮(14)在三乙胺作添加剂的条件下,可以获得中等收率的偶联的1,2,3-三唑化合物17.所有目标化合物都通过核磁共振氢谱,元素分析或高分辨质谱的确认,并测试了其生物活性.结果表明,该类化合物虽无明显的杀菌活性,但在100μg/mL测试浓度下,化合物6a,6e,6k和61均表现出较好的除草活性.
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| 关 键 词： | 1 2 3-三唑 酰胺 点击化学 偶联 除草活性 |
Synthesis and Bioactivity of Novel 1-Substituted-1H-1,2,3-triazole-4-carboxamide |
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| Wang Zhenjun,Liu Bin,Li Yonghong,Zhao Weiguang.Synthesis and Bioactivity of Novel 1-Substituted-1H-1,2,3-triazole-4-carboxamide[J].Chinese Journal of Organic Chemistry,2011,31(3). |
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| Authors: | Wang Zhenjun Liu Bin Li Yonghong Zhao Weiguang |
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| Institution: | Wang,Zhenjun Liu,Bin Li,Yonghong Zhao,Weiguang(State Key Laboratory of Elemento-Organic Chemistry,National Pesticide Engineering Research Center,Nankai University,Tianjin 300071) |
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| Abstract: | 1,2,3-Triazole amide derivatives containing triazole as a bioisoster of pyrazole were designed according to bioisoteric replacement from pyrazole amide fungicide.Seventeen novel 1-substituted-1H-1,2,3-triazole-4-carboxamide derivatives were quickly synthesized through the copper(I)-catalyzed Huisgen 1,3-dipolar cycloadditions of organic azide compounds and propiolamide,which was synthesized from propiolic acid.With Cu/C as the catalyst and triethylamine as the additive,the coupling product substituted bis-1... |
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| Keywords: | 1 2 3-triazole amide click chemistry coupling herbicidal activity |
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