58884-36-9Relevant academic research and scientific papers
REAGENTS AND METHODS FOR TETRAZINE SYNTHESIS
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Paragraph 0137; 0139-0143; 0158; 0159, (2022/04/09)
Disclosed herein are mono- and di-substituted tetrazines and methods of their preparation and converting an oxetanyl ester to a thio-substituted tetrazine, which is then converted to a mono-substituted tetrazine, a di-substituted tetrazine, or a vinylether disubstituted tetrazine.
Cross-Coupling Reactions of Monosubstituted Tetrazines
Hoff, Lukas V.,Schnell, Simon D.,Tomio, Andrea,Linden, Anthony,Gademann, Karl
supporting information, p. 5689 - 5692 (2021/08/16)
A Ag-mediated Pd-catalyzed cross-coupling method for 3-bromo-1,2,4,5-tetrazine with boronic acids is presented. Electronic modification of the 1,1′-bis(diphenylphosphine)ferrocene (dppf) ligand was found to be crucial for good turnover. Using this fast method, a variety of alkyl-, heteroatom-, and halide-substituted aryl- and heteroaryl-tetrazines were prepared (29 examples, up to 87% yield).
NOVEL TETRAZINE COMPOUNDS FOR IN VIVO IMAGING
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Page/Page column 25; 32, (2020/06/19)
The present invention relates to novel tetrazine compounds of formula I, wherein one of R1-R5 is 18F, for use in pretargeted in vivo imaging. The compounds are suitable for use in click chemistry, i.e. reactions that join
Iridium-catalyzed C-H amidation of: S -tetrazines
Xiong, Huan,Gu, Yuang,Zhang, Shuning,Lu, Fengping,Ji, Qun,Liu, Lili,Ma, Peixiang,Yang, Guang,Hou, Wei,Xu, Hongtao
, p. 4692 - 4695 (2020/05/22)
An efficient, selective and scalable C-H amidation of s-tetrazines under iridium(III) catalysis is reported. This reaction features a broad substrate scope, high functional group tolerance, and air and water tolerance. This reaction also shows great potential for the rapid preparation of tri- and tetra-functional building blocks, which can be applied either in bioconjugation or synthesis of DNA-encoded library.
Installation of Minimal Tetrazines through Silver-Mediated Liebeskind-Srogl Coupling with Arylboronic Acids
Lambert, William D.,Fang, Yinzhi,Mahapatra, Subham,Huang, Zhen,Am Ende, Christopher W.,Fox, Joseph M.
supporting information, p. 17068 - 17074 (2019/11/16)
Described is a general method for the installation of a minimal 6-methyltetrazin-3-yl group via the first example of a Ag-mediated Liebeskind-Srogl cross-coupling. The attachment of bioorthogonal tetrazines on complex molecules typically relies on linkers that can negatively impact the physiochemical properties of conjugates. Cross-coupling with arylboronic acids and a new reagent, 3-((p-biphenyl-4-ylmethyl)thio)-6-methyltetrazine (b-Tz), proceeds under mild, PdCl2(dppf)-catalyzed conditions to introduce minimal, linker-free tetrazine functionality. Safety considerations guided our design of b-Tz which can be prepared on decagram scale without handling hydrazine and without forming volatile, high-nitrogen tetrazine byproducts. Replacing conventional Cu(I) salts used in Liebeskind-Srogl cross-coupling with a Ag2O mediator resulted in higher yields across a broad library of aryl and heteroaryl boronic acids and provides improved access to a fluorogenic tetrazine-BODIPY conjugate. A covalent probe for MAGL incorporating 6-methyltetrazinyl functionality was synthesized in high yield and labeled endogenous MAGL in live cells. This new Ag-mediated cross-coupling method using b-Tz is anticipated to find additional applications for directly introducing the tetrazine subunit to complex substrates.
Synthesis, structures of some unsymmetrical 3,6-disubstituted-1,2,4,5- tetrazines
Hu, Wei-Xiao,Xu, Feng
experimental part, p. 1745 - 1750 (2009/05/31)
(Chemical Equation Presented) A series of new unsymmetrical 3-phenyl-6-benzyl-1,2,4,5-tetrazine derivatives 10a-i were synthesized and characterized by IR, NMR, MS, and element analysis. The structures of 4a, 10c, 10d and 10h were analyzed by X-ray crystallography, which had intermolecular C-H...N, C-H...Cl, C-H...Π and Π...Π H interactions.
