Toward the Synthesis of Tetrazino‐tetrazine 1,3,6,8‐Tetraoxide (TTTO): An Approach to Non‐annulated 1,2,3,4‐Tetrazine 1,3‐Dioxides
Toward the Synthesis of Tetrazino‐tetrazine 1,3,6,8‐Tetraoxide (TTTO): An Approach to Non‐annulated 1,2,3,4‐Tetrazine 1,3‐Dioxides
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DOI：
10.1002/ejoc.201500923
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发表时间：
2015-10
影响因子：
2.8
通讯作者：
M. S. Klenov;O. V. Anikin;A. M. Churakov;Y. Strelenko;I. Fedyanin;I. Ananyev;V. Tartakovsky
中科院分区：
文献类型：
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作者：
M. S. Klenov;O. V. Anikin;A. M. Churakov;Y. Strelenko;I. Fedyanin;I. Ananyev;V. Tartakovsky
提出了一种合成6-（叔丁基-NNO-偶氮氧基）-5-甲硫基-1，2，3，4-四嗪-1，3-二氧化物（1）的新方法。该化合物可能是四嗪并四嗪1，3，6，8-四氧化物的前体。合成路线包括4步：双（叔丁基-NNO-偶氮氧基）甲烷的合成，后者与二甲基硝基二硫代亚氨基碳酸酯偶联得到N-硝基亚胺3，后者经O-烷基化得到O-烷基化的硝基烯胺，再与BF 3·Et 2 O反应得到1，3-二氧化四嗪1。完成了1的X射线衍射研究。
A novel approach for the synthesis of 6-(tert-butyl-NNO-azoxy)-5-methylthio-1,2,3,4-tetrazine 1,3-dioxide (1) was developed. This compound is likely to be a precursor of tetrazino-tetrazine 1,3,6,8-tetraoxide. The synthetic strategy consists of four steps: a synthesis of bis(tert-butyl-NNO-azoxy)methane, coupling of the latter with dimethyl nitrodithioimidocarbonate to give N-nitroimine 3, O-alkylation of the latter to O-alkylated nitroenamine and its reaction with BF3·Et2O to afford tetrazine 1,3-dioxide 1. An X-ray diffraction study of 1 was accomplished.