10130-23-1Relevant articles and documents
Saccharin as an organocatalyst for quinoxalines and pyrido[2,3-b[pyrazines Syntheses
Lassagne, Frederic,Chevallier, Floris,Mongin, Florence
, p. 141 - 149 (2014)
A room-temperature procedure using saccharin as catalyst has been described for the cyclocondensation of different 1,2-arylenediamines with various 1,2-dicarbonyl compounds, yielding either quinoxalines or pyrido[2,3-b] pyrazines. The reactions proceed in very short reaction times in methanol, and the target heterocycles are isolated in quantitative yields after addition of water, filtration, and drying. Substituted pyrido[2,3-b]pyrazines can also be reached regioselectively by reacting α-ketoaldehydes with 2,3-diaminopyridine. Taylor and Francis Group, LLC.
Efficient and inexpensive synthesis of benzimidazoles and quinoxalines
Raju, B. China,Theja, N. Dharma,Kumar, J. Ashok
, p. 175 - 188 (2009)
o-Phenylenediamines were reacted with carbonyl compounds, β-ketoesters, and 1,2-diketones in presence of ammonium salts to give benzimidazoles and quinoxalines in very good yields. Ammonium salts are commercial and environmentally benign catalysts. Copyright Taylor & Francis Group, LLC.
Efficient and green synthesis of 1,2-disubstituted benzimidazoles and quinoxalines using bronsted acid ionic liquid, [(CH2) 4SO3HMIM][HSO4], in water at room temperature
Beheshtiha, Yahya S.,Heravi, Majid M.,Saeedi, Mina,Karimi, Narges,Zakeri, Masumeh,Tavakoli-Hossieni, Niloofar
, p. 1216 - 1223 (2010)
1,2-Disubstituted benzimidazoles and quinoxalines have been synthesized in the presence of Brnsted acid ionic liquid, [(CH2)4SO 3HMIM][HSO4], in water at ambient temperature.
Zirconium tetrakis(dodecyl sulfate) [Zr(DS)4] as an efficient lewis acid-surfactant combined catalyst for the synthesis of quinoxaline derivatives in aqueous media
Hasaninejad, Alireza,Zare, Abdolkarim,Zolfigol, Mohammad Ali,Shekouhy, Mohsen
, p. 569 - 579 (2009)
Zirconium tetrakis(dodecyl sulfate) [Zr(DS)4] efficiently catalyzes the synthesis of quinoxaline derivatives via the condensation of 1,2-diamines with 1,2-diketones in H2O as a green media at room temperature. Using this method, the title compounds are produced in good to excellent yields and relatively short reaction times. Copyright Taylor & Francis Group, LLC.
Synthesis and application of polyvinylimidazole-based Br?nsted acidic ionic liquid grafted silica as an efficient heterogeneous catalyst in the preparation of quinoxaline derivatives
Tamami, Bahman,Sardarian, Alireza,Ataollahi, Elaheh
, p. 422 - 433 (2016)
Two types of polymer-grafted silica based on polyvinylimidazole Br?nsted acidic ionic liquids were prepared and used as new heterogeneous catalysts for the preparation of pharmaceutically important quinoxaline derivatives. These catalysts were characterized by thermogravimetric analysis, FT-IR spectroscopy, and titration. They could be recycled without considerable loss in their catalytic activity. High efficiency of the catalysts along with short reaction times, high yields, easy purification, recyclability, and simple procedure are among the advantages of these catalytic systems.
Ligand-Tuneable, Red-Emitting Iridium(III) Complexes for Efficient Triplet–Triplet Annihilation Upconversion Performance
Phillips, Kaitlin A.,Stonelake, Thomas M.,Chen, Kepeng,Hou, Yuqi,Zhao, Jianzhang,Coles, Simon J.,Horton, Peter N.,Keane, Shannon J.,Stokes, Emily C.,Fallis, Ian A.,Hallett, Andrew J.,O'Kell, Sean P.,Beames, Joseph M.,Pope, Simon J. A.
, p. 8577 - 8588 (2018)
A series of substituted 2-phenylquinoxaline ligands have been explored to finely tune the visible emission properties of a corresponding set of cationic, cyclometallated iridium(III) complexes. The electronic and redox properties of the complexes were investigated through experimental (including time-resolved luminescence and transient absorption spectroscopy) and theoretical methods. The complexes display absorption and phosphorescent emissions in the visible region that are attributed to metal to ligand charge-transfer transitions. The different substitution patterns of the ligands induce variations in these parameters. Time-dependent DFT studies support these assignments and show that there is likely to be a strong spin-forbidden contribution to the visible absorption bands at λ=500–600 nm. Calculations also reliably predict the magnitude and trends in triplet emitting wavelengths for the series of complexes. The complexes were assessed as potential sensitisers in triplet–triplet annihilation upconversion experiments by using 9,10-diphenylanthracene as the acceptor; the methylated variants performed especially well with impressive upconversion quantum yields of up to 39.3 %.
An effective microwave-induced iodine-catalyzed method for the synthesis of quinoxalines via condensation of 1,2-diamines with 1,2-dicarbonyl compounds
Bandyopadhyay, Debasish,Mukherjee, Sanghamitra,Rodriguez, Robert R.,Banik, Bimal K.
, p. 4207 - 4212 (2010)
A microwave-induced iodine-catalyzed simple, rapid and convenient synthesis of different types of quinoxalines via condensation of 1,2-diamines with 1,2-dicarbonyl compounds has been accomplished with an excellent yield.
Ketones as a new synthon for quinoxaline synthesis
Cho, Chan Sik,Ren, Wen Xiu,Shim, Sang Chul
, p. 4665 - 4667 (2007)
o-Phenylenediamines react with an array of ketones in PEG-400 at 60 °C under an atmosphere of air in the presence of KOH to afford the corresponding quinoxalines in good yields.
Radical chain reactions of α-azido ketones with tributyltin hydride: Reduction vs nitrogen insertion and 1,2-hydrogen shift in the intermediate N-stannylaminyl radicals
Benati, Luisa,Leardini, Rino,Minozzi, Matteo,Nanni, Daniele,Spagnolo, Piero,Strazzari, Samantha,Zanardi, Giuseppe,Calestani, Gianluca
, p. 3485 - 3492 (2002)
The radical chain reactions of a variety of acyclic and cyclic α-azido ketones with tributyltin hydride have been investigated. The derived N-(tributylstannyl)aminyl radicals normally undergo H-abstraction reaction yielding corresponding amines, and thence symmetrical pyrazines by subsequent self-condensation, in competition with 1,2-H-migration from the α-carbon to nitrogen leading to α-imino ketone decomposition products with loss of the chain-carrying tributyltin radical. The noteworthy occurrence of a quite uncommon radical 1,2-hydrogen-atom shift is considered to be largely due to consequent formation of a highly stable, captodative carbon-centred radical. In contrast with our previous N-stannylaminyl radicals produced from α-azido-β-keto esters, the present aminyl congeners give poor amounts (or even none) of nitrogen-inserted amides/lactams, which are envisaged to arise from intramolecular three-membered cyclisation onto the ketone moiety followed by β-scission of the resultant alkoxyl radical. It is inferred that adequate stabilisation of the eventual ring-opened carbon radical be a major factor for the successful outcome of the regiospecific nitrogen insertion process. Evidence is also presented that chemoselective attack of tris(trimethylsilyl)silyl radical to the ketone oxygen of an α-azido ketone gives rise to deazidation as a likely consequence of β-elimination of azidyl radical by the ensuing α-silyloxyalkyl radical. X-Ray crystal structure analyses of the bromo ketone 5a, the azido ketone 5b, the caprolactam 22, and the pyrazine 26 have been performed.
Oxidative Sulfonylation of Hydrazones Enabled by Synergistic Copper/Silver Catalysis
Xu, Jun,Shen, Chao,Qin, Xian,Wu, Jie,Zhang, Pengfei,Liu, Xiaogang
, p. 3706 - 3720 (2021/02/05)
A copper/silver-cocatalyzed protocol for oxidative sulfonylation of hydrazones is demonstrated. A wide range of β-ketosulfones and N-acylsulfonamides are directly synthesized in moderate to good yields. Our work provides a viable method for scalable preparation of β-ketosulfone derivatives that have found wide applications in the pharmaceutical industry.
Versatile Heteroleptic Cu(I) Complexes Based on Quino(xa)-line-Triazole Ligands: from Visible-Light Absorption and Cooperativity to Luminescence and Photoredox Catalysis
Bruschi, Cecilia,Gui, Xin,Salaeh-arae, Nasrin,Barchi, Tobia,Fuhr, Olaf,Lebedkin, Sergei,Klopper, Wim,Bizzarri, Claudia
, p. 4074 - 4084 (2021/08/27)
Four new heteroleptic Cu(I) complexes based on 1, 2, 3-triazolyl-quinoline or quinoxaline and a chelating diphosphine were prepared and fully characterised. The mononuclear derivatives absorb in the visible region, up to 600 nm, while the dinuclear complex has a long-tail absorption up to 800 nm, showing an additional electronic state corroborated by theoretical calculations. Although a methylene group between the triazole and the quino(xa)line moiety increases the bite angle and decreases the luminescence in solution, all complexes emit brightly in the solid-state. Their redox properties in the excited state were determined, proving their ability in serving as photoredox catalysts in atom transfer radical addition successfully.
Discovery of 3-arylquinoxaline derivatives as potential anti-dengue virus agents
Tseng, Chih-Hua,Han, Cheng-Ruei,Tang, Kai-Wei
, (2019/10/28)
We designed and synthesized a series of novel 3-arylquinoxaline derivatives and evaluated their biological activities as potential dengue virus (DENV) replication inhibitors. Among them, [3-(4-methoxyphenyl)quinoxalin-2-yl](phenyl)methanol (19a), [6,7-dic
