通过α-卤代酰腙与偶氮酯的[4+2]环加成反应合成1,2,3,4-四嗪类化合物  

Synthesis of 1,2,3,4-Tetrazine Derivatives via [4+2] Cycloaddition of α-Halo-N-acylhydrazones with Diazodicarboxylates

作　　者：索永波 谢明胜 陈阳光[1] 张一铭[1] 郭真[1] 李建平[1] 渠桂荣[1] 郭海明[1] 

机构地区：[1]河南师范大学化学化工学院,新乡453007

出　　处：《有机化学》2016年第3期540-546,共7页Chinese Journal of Organic Chemistry

基　　金：国家自然科学基金(Nos.21372064;21402041);高等学校博士学科点专项科研基金(No.20124104110006);国家大学生创新性实验计划(Nos.201310476035;201410476027)资助项目~~

摘　　要：1,2,3,4-四嗪类化合物作为一种高氮化合物,具有较高的能量密度,在新型含能材料领域具有潜在的应用.通过α-卤代酰腙与偶氮酯的[4+2]环加成反应,高效地构建了四氢-1,2,3,4-四嗪类化合物.反应条件温和,通过原位生成1,2-二氮杂-1,3-二烯与偶氮酯反应,无需催化剂,反应能放大到克级规模,并具有较好的底物普适性.1,2,3,4-Tetrazine derivative is a kind of nitrogen-rich compounds, which exhibits higher energetic density and potential application on the field of energy materials. In this paper, through the [4＋2] cycloaddition of α-halo-N-acylhydrazones to diazodicarboxylates, various 1,2,3,4-tetrazine derivatives could be afforded in good to excellent yields in mild reaction conditions. The 1,2-diaza-1,3-dienes were generated in situ with the help of base, subsequently, in the absence of catalyst, the [4＋2] cycloaddition proceeded well. Besides, this reaction can be performed on the gram scale and has good substrate scope.

关 键 词：1 2 3 4-四嗪 [4+2]环加成 偶氮酯 α-卤代酰腙 

分 类 号：O626[理学—有机化学]