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
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。本文通过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 manuscript, though the [4+2] cycloaddition of alpha-halo-N-acylhydrazones to diazodicarboxylates, various 1,2,3,4-tetrazine derivatives could be afforded in good to excellent yields. Meanwhile, this reaction exhibits 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 proceeds well. Besides, this reaction could be performed on the gram scale and has good substrate scope.
谢明胜、渠桂荣、张一铭、郭海明、郭真、索永波、陈阳光
制药化学工业燃料化学工业爆炸物工业
有机化学1234-四嗪4+2]环加成偶氮酯α-卤代酰腙
Organic Chemistry1234-Tetrazine[4+2] Cycloadditiondiazodicarboxylatesα-halo-N-acylhydrazones
谢明胜,渠桂荣,张一铭,郭海明,郭真,索永波,陈阳光.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[EB/OL].(2015-11-06)[2025-08-05].http://www.paper.edu.cn/releasepaper/content/201511-95.点此复制
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