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Synthesis of 1,2,3,4-Tetrazine Derivatives via [4+2] Cycloaddition of α-Halo-N-acylhydrazones with Diazodicarboxylates
Received date: 2015-11-01
Revised date: 2015-11-24
Online 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).
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.
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]. Chinese Journal of Organic Chemistry, 2016 , 36(3) : 540 -546 . DOI: 10.6023/cjoc201511001
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