1,2,3-三唑修饰黄酮的合成  

Synthesis of 1,2,3-Triazoles Substituted Flavone

作　　者：牛雁宁 袁媛[1] 董翔 吴禄勇[3] NIU Yan-ning;YUAN Yuan;DONG Xiang;WU Lu-yong(Department of Teaching and Research, Nanjing Forestry University, Huaian 223003, China;Huaian High Tech Research Institute, Lanzhou University, Huaian 223003, China;Department of Chemistry, Hainan Normal University, Haikou 571158, China)

机构地区：[1]南京林业大学教学科研部,江苏淮安223003 [2]兰州大学淮安高新技术研究院,江苏淮安223003 [3]海南师范大学化学与化工学院,海南海口571158

出　　处：《化学试剂》2018年第7期695-698,共4页Chemical Reagents

基　　金：淮安市科技计划项目(HAGZ201614)

摘　　要：以苯胺为原料,通过重氮化反应后与乙酰乙酸乙酯发生环加成反应得到中间体5-甲基-1-苯基-1H-1,2,3-三唑-4-甲酸,进一步酰氯化后与邻羟基苯乙酮反应成酯,并在碱作用下发生Baker-Venkataraman重排反应,再经过酸催化发生闭环反应合成目标化合物。产物的结构经1HNMR、13CNMR、IR、元素分析进行确认。结果显示,Baker-Venkataraman重排反应最适宜的条件为以叔丁醇钾作碱,DMF作溶剂;在闭环反应中对甲基苯磺酸为最适宜的催化剂。该合成路线原料易得、成本较低、操作简单。In this work,aniline was used as raw materials,after the diazotization reaction,it was reacted with ethyl acetoacetate by cycloaddition reaction to form the intermediate 5-methyl-1-phenyl-1 H-1,2,3-triazole-4-carboxylic acid.After the intermediate was treated with SOCl_2,and further reacted with ortho-hydroxyacetophenone,the classical Baker-Venkataraman rearrangement was occured under the strong base. Finally,the target compound was synthesized by ring-closing reaction under the acid catalysis. The structure of the product was confirmed by ~1 HNMR,^（13）CNMR,IR,and elemental analysis.The results showed that the most suitable synthesis conditions for Baker-Venkataraman rearrangement reaction were using potassium tert-butanol as base and DMF as solvent,the most suitable catalyst for ring-closing reaction was using p-toluenesulfonic acid.The synthetic method has advantages on readily available materials,low cost,simple operation.

关 键 词：1 2 3-三氮唑 合成 黄酮 

分 类 号：TQ245.3[化学工程—有机化工]