19455-88-0Relevant academic research and scientific papers
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
A general and efficient entry to asymmetric tetrazines for click chemistry applications
Wang, Danzhu,Chen, Weixuan,Zheng, Yueqin,Dai, Chaofeng,Wang, Lifang,Wang, Binghe
, p. 171 - 177 (2013/09/02)
The importance of click chemistry is widely recognized. Among all the known click reactions, those involving tetrazines represent the fastest click reactions reported and are generating a great deal of interest. However, there is no efficient entry to asymmetric tetrazines and those with strong electron withdrawing groups, which limits the development of this field. Herein, we report a general and efficient entry to asymmetric tetrazines with strongly electron withdrawing groups.
NOVEL TETRAZINES AND METHOD OF SYNTHESIZING THE SAME
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Paragraph 0276, (2013/10/22)
Provided herein, inter alia, are compositions and methods of synthesis and detection of tetrazines and diazonorcaradienes.
Metal-catalyzed one-pot synthesis of tetrazines directly from aliphatic nitriles and hydrazine
Yang, Jun,Karver, Mark R.,Li, Weilong,Sahu, Swagat,Devaraj, Neal K.
supporting information; experimental part, p. 5222 - 5225 (2012/07/14)
Paving the way: The lack of convenient synthetic methods is a significant roadblock to the broader use of 1,2,4,5-tetrazines in bioorthogonal chemistry and functional materials. Lewis acid metal catalysts-most notably divalent nickel and zinc salts-are described to catalyze the one-pot synthesis of 1,2,4,5-tetrazines directly from aliphatic nitriles (see scheme). Copyright
Small Rings, 90. - Peralkyl-Substituted Tetrahedranes
Maier, Guenther,Fleischer, Frank,Kalinowski, Hans-Otto
, p. 173 - 186 (2007/10/02)
Photolysis of the diazo compounds 4a, b generates adamantyltri-tert-butyltetrahedrane (9a) and tri-tert-butylisopropyltetrahedrane (9b), and the corresponding cyclobutadienes 10a, b.In contrast to tetrahedrane 9a, which results from an intramolecular addition in carbene 7a and also from photoisomerization of cyclobutadiene 10a, the only source for tetrahedrane 9b is the cheletropic cycloaddition of the carbenic center to the cyclopropene double bond in the photochemically produced carbene 7b.Tetrahedrane 9b is remarkable in its kinetic and thermal instability, which is caused by the reduced "corset effect" in this compoound.An additional access to this tetrahedrane is possible via the diazomethanes 34A and 34B.The pyridazines 17b and 41, which are formed by thermolysis of the diazo compounds 4b, 34A and 34B lead to the azetes 19 and 43.Last but not least 17b and 41 are interesting molecules themselves because of their inherent chirality. - Key Words: Tetrahedranes / Cyclobutadienes / Azetes / Cyclopropenyldiazomethanes / Pyridazines: chirality, ring inversion, valence isomers
A New Synthesis of 6-(Alkyl)amino-3-aryl(alkyl)-1,2,4,5-tetrazines
Counotte-Potman, Anda,Plas, Henk C. van der
, p. 123 - 127 (2007/10/02)
A new method for the preparation of 6-(alkyl)amino-3-aryl(alkyl)-1,2,4,5-tetrazines is described.Dissolving 3-aryl(alkyl)-1,2,4,5-tetrazines in liquid ammonia or a primary aliphatic amine at -35 deg C to -40 deg C, followed by addition of potassium permanganate gives the title compounds in reasonable to excellent yields.
