14141-66-3Relevant academic research and scientific papers
Redox potential tuning of s-tetrazine by substitution of electron-withdrawing/donating groups for organic electrode materials
Kwon, Ji Eon,Lee, Kyunam,Min, Dong Joo,Park, Hyunji,Park, Soo Young
, (2021/06/12)
Herein, we tune the redox potential of 3,6-diphenyl-1,2,4,5-tetrazine (DPT) by introducing various electron-donating/withdrawing groups (methoxy, t-butyl, H, F, and trifluoromethyl) into its two peripheral benzene rings for use as electrode material in a
Catalyst-free photooxidation reaction from 1,4-dihydropyridazine to pyridazine under air
Fujii, Hideaki,Itoh, Kennosuke,Karaki, Fumika,Kiguchi, Takuto,Konishi, Kazuhide,Sato, Noriko
supporting information, (2021/09/16)
In the inverse electron-demand Diels–Alder (iEDDA) reactions between tetrazines and strained alkenes, a mixture of 1,4-dihydropyridazine isomers are formed first, and they are then oxidized to pyridazines. Although the products of these related oxidation processes converge as pyridazines, the oxidation rate is quite low with some substrates. In this study, we revealed that 1,4-dihydropyridazines formed in the iEDDA reactions were oxidized to pyridazines by simply irradiating with an ultraviolet light under an air atmosphere. Our experimental results implied that singlet oxygen was formed in the course of the reactions to oxidize the 1,4-dihydropyridazine molecules.
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
, p. 12277 - 12286 (2015/02/19)
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 investiga
3,6-Substituted-1,2,4,5-tetrazines: Tuning reaction rates for staged labeling applications
Wang, Danzhu,Chen, Weixuan,Zheng, Yueqin,Dai, Chaofeng,Wang, Ke,Ke, Bowen,Wang, Binghe
, p. 3950 - 3955 (2014/06/09)
Cycloaddition reactions involving tetrazines have proven to be powerful bioorthogonal tools for various applications. Conceivably, sequential and selective labeling using tetrazine-based reactions can be achieved by tuning the reaction rate. By varying th
Novel synthesis of 3,6-disubstituted-1,2,4,5-tetrazine derivatives from hydrazones by using [hydroxyl(tosyloxy)iodo]benzene
Liu, Haixuan,Wei, Yunyang
, p. 4645 - 4648 (2013/08/23)
A mild and efficient protocol for the construction of 1,4-dihydro-3,6- disubstituted-1,4-bis(p-toluenesulfonyl)-1,2,4,5-tetrazines from p-toluenesulfonyl hydrazones mediated by [hydroxyl(tosyloxy)iodo]benzene in the presence of pyridine has been developed. This protocol affords the products in good to excellent yields. The corresponding 3,6-disubstituted-1,2,4,5-tetrazines can be easily obtained through one-step N-deprotection of p-toluensulfonyl groups and aromatization by tetrabutyl ammonium fluoride in THF. A mechanism has been proposed.
Cycloadditions of aryl-substituted 1,2,4-triazines with 2-cyclopropylidene-1,3-dimethylimidazolidine - Zwitterions as discrete intermediates
Ernd, Michael,Heuschmann, Manfred,Zipse, Hendrik
, p. 1491 - 1518 (2007/10/03)
Cycloadditions of 2-cyclopropylidene-1,3-dimethylimidazolidine (1), a strong, electron-rich C-nucleophile, with a variety of aryl-substituted 1,2,4-triazines occur at temperatures between -100 and +100°, depending on the substitution pattern. At low tempe
Tetrazoles: XLIV. Synthesis and chemical properties of 5-substituted 2-triphenylmethyltetrazoles
Myznikov,Artamonova,Bel'skii,Stash,Skvortsov,Koldobskii
, p. 1360 - 1369 (2007/10/03)
Tritylation of tetrazole and its 5-substituted derivatives with triphenylmethyl chloride under conditions of phase-transfer catalysis regioselectively yields the corresponding 5-substituted 2-trityltetrazoles which can be used to protect N-H bonds in nitrogen-containing heterocycles and O-H bonds in primary alcohols. Thermolysis of 2-trityltetrazoles in benzonitrile leads to 3,6-disubstituted 1,2,4,5-tetrazines. Thermal transformation of the same compounds in dodecane follows a radically different mechanism, resulting in formation of difficultly accessible 8,8-diphenylheptafulvenes. The structure of the latter was proved by X-ray analysis.
