1010-60-2Relevant articles and documents
A novel and convenient process for the selective oxidation of naphthalenes with hydrogen peroxide
Shi, Feng,Tse, Man Kin,Beller, Matthias
, p. 303 - 308 (2007)
A practical ruthenium phase-transfer catalyst (Ru-PTC) system for the oxidation of naphthalene derivatives has been developed. Substituted 1,4-quinones are obtained in good selectivity and yield in water without the addition of any organic solvent and acid. By applying the optimized conditions the feed additive menadione (vitamin K3) is obtained from 2-methylnaphthalene with 64 % yield and 73 % selectivity.
The preparation and characterization of a laccase nanogel and its application in naphthoquinone synthesis
Jia, Honghua,Zhong, Chao,Huang, Fan,Wang, Chunming,Jia, Lisha,Zhou, Hua,Wei, Ping
, p. 451 - 458 (2013)
Laccase from Trametes versicolor 51639 was encapsulated on the nanoscale. The laccase nanogel was prepared by polyacrylamide encapsulation as a result of N-acryloxysuccinimide modification and in situ polymerization. Size-exclusion chromatography, fluorescence resonance energy transfer, dynamic light scattering, and transmission electron microscopy were employed to characterize the laccase nanogel. Higher thermal, pH, and storage stability and organic-solvent tolerance of the laccase nanogel were indicated without activity loss. Moreover, the laccase nanogel was used to synthesize naphthoquinones from hydroquinones with a 10-15% greater overall yield than that of native laccase. Copyright
Selective halogenation of 1,4-benzoquinones and 1,4-naphthoquinones with copper(II) halide adsorbed on alumina
Singh,Khanna
, p. 2083 - 2089 (1993)
1,4-Benzoquinone or 1,4-naphthoquinone and their derivatives have been halogenated selectively at quinonoid positions with copper(II) halide adsorbed on neutral alumina followed by refluxing in halobenzene to give mono-, di-, tri- and tetra-haloquinones.
Ruthenium-catalyzed C-H oxygenation of quinones by weak O-coordination for potent trypanocidal agents
Dias, Gleiston G.,Rogge, Torben,Kuniyil, Rositha,Jacob, Claus,Menna-Barreto, Rubem F. S.,Da Silva Júnior, Eufranio N.,Ackermann, Lutz
, p. 12840 - 12843 (2018)
Ruthenium-catalysis enabled the C-5 selective C-H oxygenation of naphthoquinones, and also sets the stage for the site-selective introduction of a hydroxyl group into anthraquinones. A-ring modified naphthoquinoidal compounds represent an important class of bioactive quinones for which the present study encompasses the first C-H oxygenation strategy by weak O-coordination.
REGIOSPECIFIC ADDITIONS OF SOME SIMPLE DIENES TO HALOQUINONES
Boisvert, Louise,Brassard, Paul
, p. 2453 - 2456 (1983)
Some simple dienes have been shown to react regiospecifically with haloquinones; the adducts can be oxidized without loss of the oxygenated function or aromatized to a variety of natural products and useful intermediates.
Electrochemical chlorination and bromination of electron-deficient C[sbnd]H bonds in quinones, coumarins, quinoxalines and 1,3-diketones
Yu, Dan,Ji, Ruixue,Sun, Zhihui,Li, Wenjie,Liu, Zhong-Quan
supporting information, (2021/11/16)
The electrochemistry-promoted chlorination and bromination of electron-deficient C[sbnd]H bonds was developed, using quinones, coumarins, quinoxalines and 1,3-diketones. This protocol features readily available and safe halogen sources (hydrochloric acid and KBr), high site-selectivity and mild reaction conditions. It could provide an efficient access to a series of chlorinated and brominated quinones, coumarins, quinoxalines and 1,3-diketones.
Ligand-based design, synthesis and biochemical evaluation of potent and selective inhibitors of Schistosoma mansoni dihydroorotate dehydrogenase
Calil, Felipe A.,David, Juliana S.,Chiappetta, Estela R.C.,Fumagalli, Fernando,Mello, Rodrigo B.,Leite, Franco H.A.,Castilho, Marcelo S.,Emery, Flavio S.,Nonato, M.Cristina
, p. 357 - 366 (2019/02/19)
Schistosomiasis ranks second only to malaria as the most common parasitic disease worldwide. 700 million people are at risk and 240 million are already infected. Praziquantel is the anthelmintic of choice but decreasing efficacy has already been documented. In this work, we exploited the inhibition of Schistosoma mansoni dihydroorotate dehydrogenase (SmDHODH) as a strategy to develop new therapeutics to fight schistosomiasis. A series of quinones (atovaquone derivatives and precursors) was evaluated regarding potency and selectivity against both SmDHODH and human DHODH. The best compound identified is 17 (2-hydroxy-3-isopentylnaphthalene-1,4-dione) with IC50 = 23 ± 4 nM and selectivity index of 30.83. Some of the new compounds are useful pharmacological tools and represent new lead structures for further optimization.