34906-29-1Relevant academic research and scientific papers
ELECTROCHEMICAL REDUCTION OF HYDROGENATED 2-PYRIMIDONES ON A GRAPHITE E ECTRODE
Kadysh, V. P.,Stradyn', Ya. P.,Khanina, E. L.,Dubur, G. Ya.,Mutsenietse, D. Kh.
, p. 95 - 99 (1985)
A rotating disk-ring graphite electrode was used to show that the first step in the electrochemical oxidation of substituted 2-oxo-1,2,3,4-tetrahydropyrimidines in anhydrous acetonitrile corresponds to a two-electron process and leads to the formation of
Interrogation of 2,2′-Bipyrimidines as Low-Potential Two-Electron Electrolytes
Griffin, Jeremy D.,Pancoast, Adam R.,Sigman, Matthew S.
, p. 992 - 1004 (2021/01/25)
As utilization of renewable energy sources continues to expand, the need for new grid energy storage technologies such as redox flow batteries (RFBs) will be vital. Ultimately, the energy density of a RFB will be dependent on the redox potentials of the respective electrolytes, their solubility, and the number of electrons stored per molecule. With prior literature reports demonstrating the propensity of nitrogen-containing heterocycles to undergo multielectron reduction at low potentials, we focused on the development of a novel electrolyte scaffold based upon a 2,2′-bipyrimidine skeleton. This scaffold is capable of storing two electrons per molecule while also exhibiting a low (～-2.0 V vs Fc/Fc+) reduction potential. A library of 24 potential bipyrimidine anolytes were synthesized and systematically evaluated to unveil structure-function relationships through computational evaluation. Through analysis of these relationships, it was unveiled that steric interactions disrupting the planarity of the system in the reduced state could be responsible for higher levels of degradation in certain anolytes. The major decomposition pathway was ultimately determined to be protonation of the dianion by solvent, which could be reversed by electrochemical or chemical oxidation. To validate the hypothesis of strain-induced decomposition, two new electrolytes with minimal steric encumbrance were synthesized, evaluated, and found to indeed exhibit higher stability than their sterically hindered counterparts.
Iridium-Catalyzed Asymmetric Hydrogenation of 4,6-Disubstituted 2-Hydroxypyrimidines
Feng, Guang-Shou,Shi, Lei,Meng, Fan-Jie,Chen, Mu-Wang,Zhou, Yong-Gui
, p. 6415 - 6419 (2018/10/15)
An efficient iridium-catalyzed hydrogenation of 4,6-disubstituted 2-hydroxypyrimidines has been achieved, giving chiral cyclic ureas with excellent diastereoselectivities and up to 96% ee of enantioselectivities. In the presence of the in situ generated h
Synthesis of dihydropyrimidine α,μ3-diketobutanoic acid derivatives targeting HIV integrase
Sari, Ozkan,Roy, Vincent,Métifiot, Mathieu,Marchand, Christophe,Pommier, Yves,Bourg, Stéphane,Bonnet, Pascal,Schinazi, Raymond F.,Agrofoglio, Luigi A.
, p. 127 - 138 (2015/10/28)
The synthesis and antiviral evaluation of a series of dihydropyrimidinone and thiopyrimidine derivatives bearing aryl α,γ-diketobutanoic acid moiety are described using the Biginelli multicomponent reaction as key step. The most active among 20 synthesized novel compounds were 4c, 4d and 5b, which possess nanomolar HIV-1 integrase (IN) stand transfer (ST) inhibition activities. In order to understand their mode of interactions within the IN active site, we docked all the compounds into the previously reported X-ray crystal structure of IN. We observed that compounds 4c, 4d and 5b occupied an area close to the two catalytic Mg2+ ions surrounded by their chelating triad (E221, D128 and D185), DC16, Y212 and the β-diketo acid moiety of 4c, 4d and 5b chelating Mg2+. As those compounds lack anti-HIV activities in cell, their prodrugs were synthetized. The prodrug 4c′ exhibited an anti-HIV activity of 0.19 μM in primary human lymphocytes with some cytotoxicity. All together, these results indicate that the new analogs potentially interact within the catalytic site with highly conserved residues important for IN catalytic activity.
Synthesis of novel nucleosides and stereoselectivity of N-glycosidation
Michigami, Kyosuke,Uchida, Satoshi,Adachi, Miho,Hayashi, Masahiko
, p. 595 - 599 (2013/07/27)
An efficient synthetic route for novel nucleosides has been realized. We report the formation of a-isomers in spite of neighboring group participation by the benzoyl group at the 2-position in N-glycosidation as well as discuss the stereoselectivity obser
Efficient aerobic oxidative dehydrogenation of dihydropyrimidinones and dihydropyrimidines
Han, Bing,Han, Run-Feng,Ren, Yu-Wei,Duan, Xiao-Yong,Xu, Yi-Chuan,Zhang, Wei
, p. 5615 - 5620 (2011/08/09)
4-Substituted dihydropyrimidinones and dihydropyrimidines were first efficient aerobic oxidized to the corresponding pyrimidinones and pyrimidines, respectively, in high yields by molecular oxygen in the presence of catalytic amount of N-hydroxyphthalimid
Photochemical preparation of pyrimidin-2(1 H)-ones by rhenium(I) complexes with visible light
Liu, Qiang,Li, Ya-Nan,Zhang, Hui-Hui,Chen, Bin,Tung, Chen-Ho,Wu, Li-Zhu
experimental part, p. 1444 - 1447 (2011/04/27)
With visible light irradiation (λ > 400 nm) of rhenium(I) complexes (P1-P4), a photochemical conversion from 3,4-dihydropyrimidin-2(1H)- ones to pyrimidin-2(1H)-ones at room temperature has been achieved with good to excellent yields in CH3CN-H
REACTIONS OF 1-METHYL-DERIVATIVES OF 2-OXO-1,2,3,4-TETRAHYDROPYRIMIDINE WITH PHOSPHORUS PENTACHLORIDE AND PHOSPHORUS OXYCHLORIDE
Khanina, E. L.,Liepin'sh, E. E.,Mutsenietse, D. Kh.,Dubur, G. Ya.
, p. 554 - 557 (2007/10/02)
In the reaction of 4-phenyl- and 4,6-diphenyl-1-methyl-2-oxo-5-ethoxycarbonyl-1,2,3,4-tetrahydropyrimidines with phosphorus pentachloride, oxidation and dealkylation takes place in addition to chlorination and as result one obtained 4-phenyl- and 4,6-diph
