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

doi:10.6023/cjoc201511001

有机化学 ›› 2016, Vol. 36 ›› Issue (3): 540-546.DOI: 10.6023/cjoc201511001 上一篇下一篇

研究论文

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

索永波, 谢明胜, 陈阳光, 张一铭, 郭真, 李建平, 渠桂荣, 郭海明

河南师范大学化学化工学院新乡 453007

收稿日期:2015-11-01 修回日期:2015-11-24 发布日期:2015-12-04
通讯作者: 郭海明 E-mail:guohm518@hotmail.com
基金资助:
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)和国家大学生创新性实验计划(Nos. 201310476035, 201410476027)资助项目.

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

Suo Yongbo, Xie Mingsheng, Chen Yangguang, Zhang Yiming, Guo Zhen, Li Jianping, Qu Guirong, Guo Haiming

School of Chemistry and Chemical Engineering, Henan Normal University, Xinxiang 453007

Received:2015-11-01 Revised:2015-11-24 Published:2015-12-04
Supported by:
Project supported by the National Natural Science Foundation of China (Nos. 21372064, 21402041), the Research Fund for the Doctoral Program of Higher Education (No. 20124104110006), and the Creative Experimental Project of National Undergraduate Students (Nos. 201310476035, 201410476027).

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摘要/Abstract

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.

关键词: 1,2,3,4-四嗪, [4+2]环加成, 偶氮酯, α-卤代酰腙

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.

Key words: 1,2,3,4-tetrazine, [4+2] cycloaddition, diazodicarboxylates, α-halo-N-acylhydrazones

引用此文

索永波, 谢明胜, 陈阳光, 张一铭, 郭真, 李建平, 渠桂荣, 郭海明. 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[J]. 有机化学, 2016, 36(3): 540-546.

Suo Yongbo, Xie Mingsheng, Chen Yangguang, Zhang Yiming, Guo Zhen, Li Jianping, Qu Guirong, Guo Haiming. Synthesis of 1,2,3,4-Tetrazine Derivatives via [4+2] Cycloaddition of α-Halo-N-acylhydrazones with Diazodicarboxylates[J]. Chin. J. Org. Chem., 2016, 36(3): 540-546.

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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

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