58884-40-5Relevant academic research and scientific papers
Ortho-Functionalized Aryltetrazines by Direct Palladium-Catalyzed C-H Halogenation: Application to Fast Electrophilic Fluorination Reactions
Testa, Christelle,Gigot, élodie,Genc, Semra,Decréau, Richard,Roger, Julien,Hierso, Jean-Cyrille
, p. 5555 - 5559 (2016)
A general catalyzed direct C-H functionalization of s-tetrazines is reported. Under mild reaction conditions, N-directed ortho-C-H activation of tetrazines allows the introduction of various functional groups, thus forming carbon-heteroatom bonds: C-X (X=I, Br, Cl) and C-O. Based on this methodology, we developed electrophilic mono- and poly-ortho-fluorination of tetrazines. Microwave irradiation was optimized to afford fluorinated s-aryltetrazines, with satisfactory selectivity, within only ten minutes. This work provides an efficient and practical entry for further accessing highly substituted tetrazine derivatives (iodo, bromo, chloro, fluoro, and acetate precursors). It gives access to ortho-functionalized aryltetrazines which are difficult to obtain by classical Pinner-like syntheses.
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.
PROCESS FOR PREPARING FUNCTIONALIZED 1,2,4,5-TETRAZINE COMPOUNDS
-
Page/Page column 37, (2017/06/29)
The present invention relates to a process for the synthesis of 3,6 functionalized 1,2,4,5-tetrazine compounds of formula (I); wherein A and B being the same; and wherein at least one of R1, R1', R2 and R2' and at least one of R10 and R10' is a halogen atom or acetate group; said process comprising reacting the corresponding 1,2,4,5-tetrazine compounds wherein at least one of R1, R1', R2 and R2' and at least one of R10 and R10' is a hydrogen atom with an oxidative reagent in presence of a catalyst.
