78751-23-2Relevant academic research and scientific papers
Electrochemical Cross-Coupling of C(sp2)?H with Aryldiazonium Salts via a Paired Electrolysis: an Alternative to Visible Light Photoredox-Based Approach
Jiang, Yang-ye,Dou, Gui-yuan,Zhang, Luo-sha,Xu, Kun,Little, R. Daniel,Zeng, Cheng-chu
, p. 5170 - 5175 (2019/11/13)
Photoredox-based C?H bond functionalization constitutes one of the most powerful and atom-economical approaches to organic syntheses. During this type of reaction, single electron transfer takes place between the photocatalyst (PC) and redox- active substrates. Electrosynthesis also involves electron transfer between substrates and electrodes. In this paper, we focus upon electrochemical cross-coupling of C(sp2)?H with aryldiazonium salts and have developed an efficient electrochemical approach to the Minisci-type arylation reaction. The constant current paired electrosynthesis proceeds in a simple undivided cell without external supporting electrolyte, features a wide range of substrates and is easy to scale-up. These results demonstrate that photoredox-based cross-coupling of C(sp2)?H with aryldiazonium salts can also proceed successfully under paired electrolysis conditions, thereby contributing to understanding of the parallels between photosynthesis and electrosynthesis. (Figure presented.).
A niobium-catalyzed coupling reaction of α-keto acids with: Ortho -phenylenediamines: Synthesis of 3-arylquinoxalin-2(1 H)-ones
Ebersol, Camila,Rocha, Nicole,Penteado, Filipe,Silva, Márcio S.,Hartwig, Daniela,Lenard?o, Eder J.,Jacob, Raquel G.
supporting information, p. 6154 - 6160 (2019/11/20)
A general methodology to access valuable 3-arylquinoxalin-2(1H)-ones was developed, by the reaction of α-keto acids with ortho-phenylenediamines in the presence of ammonium niobium oxalate (ANO) as a catalyst. The reactions were conducted in only 10 min under ultrasonic irradiation as an alternative energy source, affording water as the only co-product. A total of twenty-three different 3-arylquinoxalin-2(1H)-ones were selectively obtained in good to excellent yields by this atom-efficient protocol. Additionally, 1H-15N HMBC experiments were used to reveal the regioisomerism of the obtained products.
Chemoselective synthesis of 3,6,7-trisubstituted 2-(2,3:5,6-di-O-isopropylidene-β-D-mannofuranosyloxy]- and 2-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyloxy)quinoxaline derivatives
Fathalla, Walid
, p. 67 - 72 (2015/03/14)
[Figure not available: see fulltext.] A series of quinoxaline O-nucleosides, 3,6,7-trisubstituted 2-(2,3:5,6-di-O-isopropylidene-β-D-mannofuranosyl-1-yl)quinoxalines and 2-(2-acetamido-2-deoxy-3,4,6-tri-O-acetyl-β-D-glucopyranosyl)quinoxalines, was prepared by the reaction of 3,6,7-trisubstituted quinoxalin-2(1H)-ones with the corresponding protected α-chlorosugars in the presence of NaH. The reaction proceeded chemoselectively to give products of O-substitution with β-configuration at anomeric carbon, as proved by NMR data. The deprotection of the 1-(2-acetamido-2-deoxy-3,4,6-tri-O-acetyl-β-D-glucopyranosyl)quinoxalines was achieved by stirring in ammonia-methanol mixture to afford free O-quinoxaline nucleoside analogs.
Facile One-Pot Synthesis of Benzimidazole and Quinoxalin-2(1 H)-one Scaffolds via Two-Component Coupling Reaction, Deprotection, and Intermolecular Cyclization
Chen, Zhong-Zhu,Tang, Ying,Zuo, Lei,Tang, Dian-Yong,Zhang, Jin,Xu, Zhi-Gang
supporting information, p. 2518 - 2520 (2015/07/27)
Two scaffolds, namely benzimidazole and quinoxalin-2(1H)-one, were synthesized by treating 2-(N-Boc-amino)phenylisocyanide (Boc: tert-butoxycarbonyl) with carboxylic acids and glyoxylic acids, respectively. The target compounds were generated directly aft
An efficient synthetic protocol for quinoxalinones, Benzoxazinones, and benzothiazinones from 2-oxo-2-aryl-acetyl bromide precursors
Nagaraj, Muthupandi,Sathiyamoorthy, Sithuraj,Boominathan, Muthusamy,Muthusubramanian, Shanmugam,Bhuvanesh, Nattamai
, p. 1146 - 1151 (2013/10/21)
α-Bromoketones undergo selenium dioxide oxidation to yield reactive 2-oxo-2-arylacetyl bromides that are trapped by aryl-1,2-diamines, 1,2-aminophenol or 1,2-aminothiophenol to give quinoxalinones, benzoxazinones, and benzothiazinones, respectively, in go
Revisiting the Hinsberg reaction: Facile and expeditious synthesis of 3-substituted quinoxalin-2(1H)-ones under catalyst-free conditions in water
Murthy, Sabbavarapu Narayana,Madhav, Bandaru,Nageswar, Yadavalli Venkata Durga
experimental part, p. 1216 - 1220 (2010/08/21)
Substituted benzene-1,2-diamine reacted with various α-keto esters at 50° under mild conditions for 15 min using H2O as reaction medium, providing a variety of 3-substituted quinoxalinone derivatives in excellent yields. The reaction was instantaneous, and products were isolated by simple filtration.
Synthesis and study of new 2-aryl-1-(4-nitrophenyl)-1,1a-dihydroazireno[1, 2-a]quinoxaline derivatives
Zbruyev,Yaremenko,Chebanov,Desenko,Shishkin,Lukinova,Knyazeva
, p. 362 - 368 (2007/10/03)
New derivatives of photochromic 2-aryl-1-(4-nitrophenyl)-1,1a- dihydroazireno[1,2-a]quinoxalines were synthesized by condensation of 4-methyl-and 4,5-dimethyl-1,2-phenylenediamine with 1,3-diaryl-2,3- dibromopropan-1-ones. The reactions of 4-methyl-1,2-ph
Quinoxalin-2-one derivatives, compositions which protect useful plants and comprise these derivatives, and processes for their preparation and their use
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Page/Page column 34, (2008/06/13)
Compounds of the formula (I) and salts thereof in which X is O or S; (Y)n=n substituents Y, n is 0, 1, 2, 3 or 4, R1 is H, OH, NH2, (C1-C4)-alkylamino, di-[(C1-C4)-alkyl]amino or optionally substituted (C1-C10)-alkyl, (C3-C10)-alkenyl, (C3-C10)-alkynyl or (C1-C10)-alkoxy, (C3-C10)-cycloalkyl, (C4-C10)-cycloalkenyl, aryl or heterocyclyl, R2 is H or optionally substituted (C1-C10)-alkyl, (C3-C10)-alkenyl, (C3-C10)-alkynyl, (C3-C10)-cycloalkyl, (C4-C10)-cycloalkenyl, aryl or heterocyclyl, where the radicals Y are as defined in claim 1 are suitable for use as safeners for crop plants or useful plants against the phytotoxic actions of agrochemicals such as pesticides in these plants.
Tyrphostins. 5. Potent inhibitors of platelet-derived growth factor receptor tyrosine kinase: Structure-activity relationships in quinoxalines, quinolines, and indole tyrphostins
Gazit, Aviv,App, Harald,McMahon, Gerald,Chen, Jefferey,Levitzki, Alexander,Bohmer, Frank D.
, p. 2170 - 2177 (2007/10/03)
A series of 3-indoleacrylonitrile tyrphostins, 2-chloro-3- phenylquinolines, and 3-arylquinoxalines were prepared and tested for inhibition of platelet-derived growth factor receptor tyrosine kinase (PDGF- RTK) activity. The potency of the inhibitors was found to be quinoxalines > quinolines > indoles. Lipophilic groups (methyl, methoxy) in the 6 and 7 positions and phenyl at the 3 position of quinoxalines and quinolines were essential for potency, in contrast to the hydrophilic catechol group in tyrphostins active against EGFR kinase inhibition at different sites. The inhibitors showed selectivity for PDGF and were not active against EGF receptor and HER-2/c-ErbB-2 receptor.
Reactions of Mesoionic Five-Membered Heterocycles with o-Quinonoid Compounds, IV. Mono- and Tricyclic 1,3-Thiazolium-4-olates, 1,3-Dithiolylium-4-olates
Friedrichsen, Willy,Schroeer, Wolf-D.,Schwarz, Ingo,Boettcher, Andreas
, p. 609 - 621 (2007/10/02)
Monocyclic 1,3-thiazolium-4-olates (10) react with o-quinonoid compounds to give cycloadducts (12,13); tricyclic 1,3-thiazolium-4-olates (14,15) yield compounds (17,18,19,20) which can formally be derived from a ketene tautomer (C). 1,3-Dithiolylium-4-olates are borderline cases; both (32) and adducts (34) were obtained. - Keywords: o-Quinones, Heterocycles
