64500-06-7Relevant articles and documents
Organocatalytic and Scalable Syntheses of Unsymmetrical 1,2,4,5-Tetrazines by Thiol-Containing Promotors
Mao, Wuyu,Shi, Wei,Li, Jie,Su, Dunyan,Wang, Xiaomeng,Zhang, Lyuye,Pan, Lili,Wu, Xiaoai,Wu, Haoxing
, p. 1106 - 1109 (2019)
Despite the growing application of tetrazine bioorthogonal chemistry, it is still challenging to access tetrazines conveniently from easily available materials. Described here is the de novo formation of tetrazine from nitriles and hydrazine hydrate using a broad array of thiol-containing catalysts, including peptides. Using this facile methodology, the syntheses of 14 unsymmetric tetrazines, containing a range of reactive functional groups, on the gram scale were achieved with satisfactory yields. Using tetrazine methylphosphonate as a building block, a highly efficient Horner–Wadsworth–Emmons reaction was developed for further derivatization under mild reaction conditions. Tetrazine probes with diverse functions can be scalably produced in yields of 87–93 %. This methodology may facilitate the widespread application of tetrazine bioorthogonal chemistry.
Method for preparing tetrazine compound and application thereof
-
Paragraph 0070-0075, (2020/12/14)
The invention discloses a novel method for preparing a tetrazine compound. The method uses nitrile and hydrazine hydrate to carry out various substitutions in the presence of a mercaptan catalyst to obtain tetrazine compounds with various functions, and is convenient for further modification and transformation of the tetrazine compounds, thereby obtaining more tetrazine derivatives with special functions. In addition, the method for preparing the tetrazine compound has the advantages that reaction conditions are mild, reagents are easy to obtain, the method is environmentally friendly, the product yield is high, and gram-scale production can be carried out. The problems in the prior art that when hydrazine hydrate is adopted for preparing tetrazine compounds, substitution is single, the types of the obtained tetrazine compounds are limited, the preparation conditions are harsh, and large-scale production cannot be achieved are solved.
