1,2,4,5-Tetrazine Derivatives from Arylsulfonylhydrazones

Hui-Jing Li and Yan-Chao Wu report on the synthesis of 1,2,4,5-tetrazine derivatives.

Chlorination of Arylaldehyde-Derived Arylsulfonylhydrazones with N-Chlorosuccinimide Leading to 1,2,4,5-Tetrazine Derivatives: Y.-Z. Ji, H.-J. Li, Y. Liu, Y.-C. Wu
Synthesis 2019, DOI: 10.1055/s-0039-1690712

1,2,4,5-Tetrazine derivatives are important heterocycles which – further to the classical applications in organic electronics, energetic materials and pharmaceuticals – have recently gained enormous attention in biomedical sciences for their use as ‘click reagents’ for labelling biomolecules and -polymers, such as antibodies and DNA, or even cells. Recently, the group of Professors Hui-Jing Li and Yan-Chao Wu from the Harbin Institute of Technology and Weihai Institute of Marine Biomedical Industrial Technology, Weihai (P. R. of China) reported an interesting approach to 1,2,4,5-tetrazine derivatives.


Professor Wu said: “A simple and effective protocol for the synthesis of 1,2,4,5-tetrazines, proceeding via NCS-mediated chlorination of arylaldehyde-derived N-tosylhydrazones, can be performed under metal-free conditions. The method can tolerate a wide range of hydrazone substrates to afford the corresponding 1,2,4,5-tetrazines in good to excellent yields.” 

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