51973-26-3Relevant academic research and scientific papers
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.
Novel synthesis of 3,6-disubstituted-1,2,4,5-tetrazine derivatives from hydrazones by using [hydroxyl(tosyloxy)iodo]benzene
Liu, Haixuan,Wei, Yunyang
, p. 4645 - 4648 (2013/08/23)
A mild and efficient protocol for the construction of 1,4-dihydro-3,6- disubstituted-1,4-bis(p-toluenesulfonyl)-1,2,4,5-tetrazines from p-toluenesulfonyl hydrazones mediated by [hydroxyl(tosyloxy)iodo]benzene in the presence of pyridine has been developed. This protocol affords the products in good to excellent yields. The corresponding 3,6-disubstituted-1,2,4,5-tetrazines can be easily obtained through one-step N-deprotection of p-toluensulfonyl groups and aromatization by tetrabutyl ammonium fluoride in THF. A mechanism has been proposed.
Diazocinones: Synthesis and conformational analysis
Robins, Lori I.,Carpenter, Richard D.,Fettinger, James C.,Haddadin, Makhluf J.,Tinti, Dino S.,Kurth, Mark J.
, p. 2480 - 2485 (2007/10/03)
1,2,4,5-Tetrazines (prepared from aryl nitriles) condense with isoxazolylcyclobutanones (prepared from 3-benzenesulfonyl-3-vinylcyclobutanol) in methanolic KOH to give conformationally restricted 6-isoxazol-5-yl-6,7- dihydro-5H-[1,2]diazocin-4-ones. The s
Synthesis and antitumor activity of s-tetrazine derivatives
Hu, Wei-Xiao,Rao, Guo-Wu,Sun, Ya-Quan
, p. 1177 - 1181 (2007/10/03)
Fifty-five compounds of s-tetrazine derivative including hexahydro-, 1,6-dihydro, 1,4-dihydro-, 1,2-dihydro- and aromatic s-tetrazine were prepared. Their antitumor activities were evaluated in vitro by MTT method for P-388 cell and SRB method for A-549 cell. The results show that there are 9 compounds which in 10-6 μM have more than 50% inhibition rate to A-549 cancer cell growth, and 7 compounds in 10-6 μM have more than 50% inhibition rate to P-388 cancer cell growth. The IC50 of compound 3q for P-388, Bel-7402, MCF-7 and A-549 are 0.6 μM, 0.6 μM, 0.5 μM and 0. 7 μM, respectively. So s-tetrazine derivative is a kind of compound which possesses potential antitumor activities and is worth to research further.
