Novel 3,6-unsymmetrically disubstituted-1,2,4,5-tetrazines: S-induced one-pot synthesis, properties and theoretical study

Li Chen; Ge Haixia; Yin Bing; She Mengyao; Liu Ping; Li Xiangdong; Li Jianli

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Novel 3,6-unsymmetrically disubstituted-1,2,4,5-tetrazines: S-induced one-pot synthesis, properties and theoretical study

机译：新型3,6-不对称双取代-1,2,4,5-四嗪：S诱导的一锅合成，性质和理论研究

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18 unprecedented tetrazines unsymmetrically substituted at C3 and C6 by an aromatic heterocycle have been successfully prepared by the S-induced reaction of aromatic nitriles with hydrazine hydrate under thermal conditions. The spectral property investigation suggests that compounds 4d, 4e, 4f, 4p, 4q, 4r, and 4v can display intense fluorescence in the visible region, and their fluorescent properties are affected by the substituents both in tetrazine and in phenyl rings. Moreover, the electrochemical behaviors of these synthesized tetrazines are demonstrated to be fully reversible. Furthermore, density functional theory (DFT) calculations for these compounds were performed to investigate their optimized structures, Fukui function and reactivity or selectivity in the inverse electron demand Diels-Alder reaction.

机译：在热条件下，通过S诱导芳族腈与水合肼的反应，成功制备了18种前所未有的在芳香族杂环上不对称取代在C3和C6处的四嗪。光谱性质研究表明，化合物4d，4e，4f，4p，4q，4r和4v可以在可见光区域显示强烈的荧光，并且它们的荧光性质受到四嗪和苯环中取代基的影响。此外，这些合成的四嗪的电化学行为被证明是完全可逆的。此外，对这些化合物进行了密度泛函理论（DFT）计算，以研究它们在逆电子需求Diels-Alder反应中的优化结构，Fukui函数以及反应性或选择性。

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《RSC Advances》 |2015年第16期|共10页
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Li Chen; Ge Haixia; Yin Bing; She Mengyao; Liu Ping; Li Xiangdong; Li Jianli;
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1. Novel 3,6-unsymmetrically disubstituted-1,2,4,5-tetrazines: S-induced one-pot synthesis, properties and theoretical study [J] . Li Chen, Ge Haixia, Yin Bing, RSC Advances . 2015,第16期

机译：新型3,6-不对称双取代-1,2,4,5-四嗪：S诱导的一锅合成，性质和理论研究
2. Synthesis, Structures of some Unsymmetrical 3,6-Disubstituted-1,2,4,5-Tetrazines [J] . Hu WX, Xu F Journal of Heterocyclic Chemistry: The International Journal of Heterocyclic Chemistry . 2008,第6期

机译：某些不对称3,6-二取代-1,2,4,5-四嗪的合成，结构
3. Synthesis of 1,2,4,5-Tetrazines,Symmetrically and Unsymmetrically 3,6-Disubstituted by N-Nucleophiles [J] . G.L.Rusinov, N.I.Latosh, I.I.Ganebnykh, Russian Journal of Organic Chemistry . 2006,第5期

机译：N-亲核试剂对称和不对称地合成3,6-二取代的1,2,4,5-四嗪
4. A STRUCTURAL ISOMER OF CL-20: SYNTHESIS, CHARACTERIZATION AND ENERGETIC PROPERTIES OF N~3,N~6-BIS(2,2,2-TRINITROTETHYL)-1,2,4,5-TETRAZINE-3,6-DIAMINE [C] . Michael Goebell, Thomas M. Klapoetke Seminar on new trends in research of energetic materials;NTREM '09 . 2009

机译：CL-20的结构异构体：N〜3，N〜6-BIS（2,2,2-三亚丁基）-1,2,4,5-四嗪-3,6-二胺的合成，表征和能量性质
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机译：1-（三乙氧基甲硅烷基）buta-13-二烯—不对称（EE）-14-二取代的13-二烯立体选择性合成的新结构单元
7. Divergent Synthesis of Monosubstituted and Unsymmetrical 3,6- Disubstituted Tetrazines from Carboxylic Ester Precursors [O] . Yixin Xie, Yinzhi Fang, Zhen Huang, 2020

机译：来自羧酸酯前体的单药物和非对称3,6-二取代四嗪的分歧合成
8. Improved Synthesis and Properties of 3,6-Diamino-1,2,4,5-Tetrazine and 3,6-Dihydrazino-1,2,4,5-Tetrazine. [R] . Coburn, M. D., Ott, D. G., Stine, J. R., 1989

机译：改进了3,6-二氨基-1,2,4,5-四嗪和3,6-二肼基-1,2,4,5-四嗪的合成和性质。

Novel 3,6-unsymmetrically disubstituted-1,2,4,5-tetrazines: S-induced one-pot synthesis, properties and theoretical study

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