Category: 23088-24-6

Wang, Qing-Qing; Xu, Kun; Jiang, Yang-Ye; Liu, Yong-Guo; Sun, Bao-Guo; Zeng, Cheng-Chu published the artcile< Electrocatalytic Minisci Acylation Reaction of N-Heteroarenes Mediated by NH4I>, HPLC of Formula: 23088-24-6, the main research area is acylpyrazine acylquinoxaline heteroaryl ketone preparation; chemoselective green Minisci acylation pyrazine quinoxaline ketoacid ammonium iodide; ammonium iodide mediator electrochem Minisci acylation pyrazine quinoxaline ketoacid; mechanism electrochem Minisci acylation pyrazine quinoxaline ketoacid.

Electron-deficient aromatic nitrogen heterocycles, particularly pyrazines and quinoxalines, underwent chemoselective and green electrochem. Minisci acylations with α-ketoacids such as pyruvic acid mediated by NH4I, LiClO4, and hexafluoroisopropanol in MeCN to give heteroaryl ketones such as 2-acetylquinoxaline in 18-65% yields. Cyclic voltammetry and control experiments were used to delineate the mechanism of the Minisci acylation; I2 formed in situ likely reacts with carboxylate anions to yield acyl hypoiodites which then undergo decarboxylation to acyl radicals.

Organic Letters published new progress about Acylation, regioselective (Minisci, chemoselective, electrochem.). 23088-24-6 belongs to class quinoxaline, and the molecular formula is C9H5N3, HPLC of Formula: 23088-24-6.

Referemce:
Quinoxaline – Wikipedia,
Quinoxaline | C8H6N2 | ChemSpider

Rao, Koppaka V.; Jackman, Dennis published the artcile< Reaction of sodium borohydride with heteroaromatic nitro compounds>, Related Products of 23088-24-6, the main research area is quinoxaline nitro reduction; quinoline nitro reduction; tetrahydronitroquinoxaline; dihydronitroquinoline.

Quinoxalines (I, R = 5-, 6-NO2, 6-CN, 6-CO2Et, 6-CF3) and 5-, 6-, 7-, 8-nitroquinoline (II) were reduced selectively by NaBH4 in HOAc at 5° to give 1,2,3,4-tetrahydro-derivatives of I and 1,2-dihydro-derivatives of II resp. 5-Nitroisoquinoline was reduced to the 1,2,3,4-tetrahydro derivative in HOAc at 5° but yielded the 1,2-dihydro derivative in aqueous MeOH.

Journal of Heterocyclic Chemistry published new progress about Reduction. 23088-24-6 belongs to class quinoxaline, and the molecular formula is C9H5N3, Related Products of 23088-24-6.

Referemce:
Quinoxaline – Wikipedia,
Quinoxaline | C8H6N2 | ChemSpider

Landquist, Justus K. published the artcile< Quinoxaline N-oxides. I. The oxidation of quinoxaline and its Bz-substituted derivatives>, Recommanded Product: 6-Quinoxalinecarbonitrile, the main research area is .

Quinoxaline (I) and its Bz-substituted-alkyl, alkoxy, halo, and acylamino derivatives are oxidized to 1- and 1,4-dioxides by organic peroxy acids. Resistance to N-oxidation is encountered in 5- and 8-substituted I. Reduction of 2,3-(O2N)2C6H3OEt with H and Raney Ni gave 3,1,2-EtOC6H3(NH2)2, oil (picrate, m. 210-12°). 2,4-Br(O2N)C6H3Me nitrated with HNO3 and H2SO4 at 40-5° gave 2,4,5-Br(O2N)2C6H2Me, m. 94-5°, which, treated with NH3 in alc. 5 h. at 120° and then reduced with Zn dust and NaOH in EtOH, yielded the 4,5-(H2N)2 analog, m. 140-1°. The following general procedure for preparation of I derivatives was used: (CHO.NaHSO3)2, an ο-phenylenediamine, and H2O were stirred 3 h. at 60°, then made alk. with KOH, and the I derivative was filtered off. The following derivatives were prepared (substituent, m.p., m.p. of 1-oxide, m.p. of 1,4-dioxide): 5-Me, 20-1°, b15, 120°, 131-2°, 192-4°; 5-EtO, 63-4°, b18 165-6°, 114-16°, -; 5-Cl (II), 60-2°, 177-9°, -; 6-iodo, 114-15°, -, -; 6-NC (III), 176-8°, -, -; 6,7-Me2, 100-1°, -, 220°; 6,7-benzo, 125-6°, -, -; 6,7-ClMe (IV), 120-2°, 166-8°, 227°; 6,7-BrMe (V), 127-8°, 167-8°, 222-4°; 6,7-Cl2 (VI), 210°, -, 206-8°; 5,8-Cl2 (VII), 205-7°, -, -; 6-Br (VIII)(prepared by the Sandmeyer reaction from the 6-NH2 compound), 48-9°, b18 146-9°, -, 223-5°; 6-AcNH (prepared from the 6-NH2 compound with Ac2O), 196.5°, -, 245-7°; 5-AcNH, -, 175-8°, 230-2° (insufficient for anal.). The following N-oxides were also prepared (substituent, m.p. 1-oxide, m.p. 1,4-dioxide): 6-Me (IX), -, 218-19°; 5,6-benzo, 158-9°, 215-16°; 5,6:7,8-dibenzo, 243-4°, -; 5-MeO, -, 222°; 6-MeO, -, 227-8°; 6-EtO, -, 192-4°; 5,6-(MeO)2, 138-40°, 220-2°; 6,7-(MeO)2, -, 264-5°; 2-Cl, 150-2°, -; 6-Cl (X), 151-2°, 211-12°. I is oxidized with equimolar AcO2H to quinoxaline 1-oxide, m. 122-3° (XI) while excess peroxy acid yields quinoxaline 1,4-dioxide, m. 241-3° (XII). Simultaneous with N-oxide formation there were obtained 2,3-dihydroxyquinoxalines which are listed below: (substituent, % yield, m.p.): IX, 1, 112°; II, 30, 142-3°; X, 15-30, 144°; VIII, 28, 132°; VII, 65, 160-1°; VI, 43, 170-70.5°; IV, 10, 172-3°; V, 12-6, 160-1°; III, 50, -; 6-O2N, 60, 150°. XI and MeI in MeCN set aside in the dark 36 h., precipitated 1-methylquinoxalinium iodide 4-oxide, m. 188-9°. XI was added cautiously to POCl3, and the mixture boiled 15 min. after the reaction subsided, poured on ice, made alk. with KOH, extracted with Et2O, and concentrated to yield 2-chloroquinoxaline, m. 46-8°. Under similar conditions XII yielded 2,3-dichloroquinoxaline; 5-methylquinoxaline 1-oxide gave 2-chloro-5-methylquinoxaline, m. 95°; and 5,6-benzoquinoxaline 1-oxide yielded 2-chloro-5,6-benzoquinoxaline, m. 120.5°. 2-C10H7NHCH2CO2Et dissolved treated in EtOH with PhN2Cl yielded 1,2-Ph2NC10H6NHCH2CO2Et, m. 135-6°, hydrogenated with Raney Ni at 60° and 50 atm. to 1,2,3,4-tetrahydro-2-oxo-7,8-benzoquinoxaline (XIII), m. 197-8°. XIII with alk. H2O2 gave 2-hydroxy-7,8-benzoquinoxaline, isolated as the hydrate, m. 275-5.5°, which was converted with POCl3 into 2-chloro-7,8-benzoquinoxaline, m. 128-9°. N-(6-nitro-o-tolyl)glycine in EtOH hydrogenated over Raney Ni at 60° and 60 atm. yielded 1,2,3,4-tetrahydro-5-methyl-2-oxoquinoxaline, m. 177-80°, readily oxidized to 2-hydroxy-5-methylquinoxaline, m. 282-3°. 2-Chloro-7,8-benzoquinoxaline and piperidine refluxed 1.5 h. gave 2-piperidino-7,8-benzoquinoxaline, m. 101.5-2.5°. 2-Piperidino-5,6-benzoquinoxaline, m. 124-5°, was similarly prepared Cl slowly passed 1 h. into 5,6-benzoquinoxaline in glacial HOAc, and the solution filtered and diluted with H2O yielded, on purification, dichloro-5,6-benzoquinoxaline, m. 187-8°. Methylation of 2,3-dihydroxy-6-nitroquinoxaline with Me2SO4 gave 3-hydroxy-1-methyl-6(or 7)-nitro-2(1H)-quinoxalinone, m. 344°. 6(or 7)-Cyano-3-hydroxy-1-methyl-2(1H)-quinoxalinone, m. 353-4°, is similarly prepared

Journal of the Chemical Society published new progress about Oxidation. 23088-24-6 belongs to class quinoxaline, and the molecular formula is C9H5N3, Recommanded Product: 6-Quinoxalinecarbonitrile.

Referemce:
Quinoxaline – Wikipedia,
Quinoxaline | C8H6N2 | ChemSpider

Climent, M. J.; Corma, A.; Hernandez, J. C.; Hungria, A. B.; Iborra, S.; Martinez-Silvestre, S. published the artcile< Biomass into chemicals: One-pot two- and three-step synthesis of quinoxalines from biomass-derived glycols and 1,2-dinitrobenzene derivatives using supported gold nanoparticles as catalysts>, Recommanded Product: 6-Quinoxalinecarbonitrile, the main research area is vicinal diol phenylenediamine gold nanoparticle oxidation cyclocondensation catalyst; dinitrobenzene vicinal diol gold nanoparticle reduction oxidation cyclocondensation catalyst; quinoxaline preparation.

An efficient and selective one-pot two-step method, for the synthesis of quinoxalines by oxidative coupling of vicinal diols with 1,2-phenylenediamine derivatives, has been developed by using gold nanoparticles supported on nanoparticulated ceria (Au/CeO2) or hydrotalcite (Au/HT) as catalysts and air as oxidant, in the absence of any homogeneous base. Reaction kinetics shows that the reaction controlling step is the oxidation of the diol to α-hydroxycarbonyl compound Furthermore, a one-pot three-step synthesis of 2-methylquinoxaline starting from 1,2-dinitrobenzene and 1,2-propanediol has been successfully carried out with 98% conversion and 83% global yield to the final product.

Journal of Catalysis published new progress about Aromatic diamines Role: RCT (Reactant), RACT (Reactant or Reagent). 23088-24-6 belongs to class quinoxaline, and the molecular formula is C9H5N3, Recommanded Product: 6-Quinoxalinecarbonitrile.

Referemce:
Quinoxaline – Wikipedia,
Quinoxaline | C8H6N2 | ChemSpider

Takai, Hitoshi; Odani, Akira; Sasaki, Yoshio published the artcile< Studies on heterocyclic carbon-13 magnetic resonance spectroscopy. XI. Nitrogen heterocycles. (1). 6-Substituted quinoline and quinoxaline derivatives>, COA of Formula: C9H5N3, the main research area is carbon NMR quinoline quinoxaline; LFER NMR heterocycle.

The assignment of 13C NMR chem. shifts of 6-substituted quinoline and quinoxaline derivatives were confirmed, and the additivity rules of 13C chem. shifts of 2-substituted naphthalene derivatives were approved for both 6-substituted quinoline and quinoxaline derivatives The correlation coefficient of meta-like positions is promoted by the linear combinations of chem. shifts at the corresponding meta position of 2-substituted naphthalene derivatives and substituent constants σπ.

Chemical & Pharmaceutical Bulletin published new progress about Linear free energy relationship. 23088-24-6 belongs to class quinoxaline, and the molecular formula is C9H5N3, COA of Formula: C9H5N3.

Referemce:
Quinoxaline – Wikipedia,
Quinoxaline | C8H6N2 | ChemSpider

Zhang, Xingjie; Xia, Aiyou; Chen, Haoyi; Liu, Yuanhong published the artcile< General and Mild Nickel-Catalyzed Cyanation of Aryl/Heteroaryl Chlorides with Zn(CN)2: Key Roles of DMAP>, Related Products of 23088-24-6, the main research area is aryl halide zinc cyanide nickel DMAP; cyanoarene preparation; heteroaryl halide zinc cyanide nickel DMAP; cyanoheteroarene preparation; nickel cyanation catalyst; DMAP cyanation mediator.

A new and general nickel-catalyzed cyanation of hetero(aryl) chlorides using less toxic Zn(CN)2 as the cyanide source has been developed. The reaction relies on the use of inexpensive NiCl2·6H2O/dppf/Zn as the catalytic system and DMAP as the additive, allowing the cyanation to occur under mild reaction conditions (50-80 °C) with wide functional group tolerance. DMAP was found to be crucial for successful transformation, and the reaction likely proceeds via a Ni(0)/Ni(II) catalysis based on mechanistic studies. The method was also successfully extended to aryl bromides and aryl iodides.

Organic Letters published new progress about Aromatic nitriles Role: SPN (Synthetic Preparation), PREP (Preparation). 23088-24-6 belongs to class quinoxaline, and the molecular formula is C9H5N3, Related Products of 23088-24-6.

Referemce:
Quinoxaline – Wikipedia,
Quinoxaline | C8H6N2 | ChemSpider

Lewis, Susan J.; Mirrlees, Margaret S.; Taylor, Peter J. published the artcile< Rationalizations among heterocyclic partition coefficients. Part 2: The azines>, Safety of 6-Quinoxalinecarbonitrile, the main research area is azine structure partition coefficient; LFER azine.

π-Values (partition substituent constants) of 246 azines are given and discussed in terms of Δπ, the difference in π-value from that expected for C6H6. It is shown that Δπ is close to zero for alkyl and most halogen groups, but for polar substituents capable of H bonding it may be as high as φ1.6. Except for peri-positions, these Δπ-values may be correlated by a set of equations specific for different types of substituent position and containing terms which sep. parameterize proton-donor and -acceptor ability. The rationale behind this treatment is justified in terms of the nature of the octanol-H2O partitioning process and the manner in which electronic effects are expected to operate, in this context and that of the individual mol. Other topics discussed include: reasons for deviations among “”irregular”” substituents; the special problems of peri-positions; multisubstitution; and some consequences of this anal. for other types of compound

Quantitative Structure-Activity Relationships published new progress about Molecular structure-property relationship, partition. 23088-24-6 belongs to class quinoxaline, and the molecular formula is C9H5N3, Safety of 6-Quinoxalinecarbonitrile.

Referemce:
Quinoxaline – Wikipedia,
Quinoxaline | C8H6N2 | ChemSpider

Lee, Hong Geun; Milner, Phillip J.; Placzek, Michael S.; Buchwald, Stephen L.; Hooker, Jacob M. published the artcile< Virtually Instantaneous, Room-Temperature [11C]-Cyanation Using Biaryl Phosphine Pd(0) Complexes>, Electric Literature of 23088-24-6, the main research area is cyanation carbon 11 aryl compound biaryl phosphine palladium catalyst; aryl nitrile carbon 11 labeled preparation.

A new radiosynthetic protocol for the preparation of [11C]aryl nitriles has been developed. This process is based on the direct reaction of in situ prepared L·Pd(Ar)X complexes (L = biaryl phosphine) with [11C]HCN. The strategy is operationally simple, exhibits a remarkably wide substrate scope with short reaction times, and demonstrates superior reactivity compared to previously reported systems. With this procedure, a variety of [11C]nitrile-containing pharmaceuticals, e.g., [11C]citalopram, were prepared with high radiochem. efficiency.

Journal of the American Chemical Society published new progress about Aromatic nitriles Role: SPN (Synthetic Preparation), PREP (Preparation) ([11C]-labeled). 23088-24-6 belongs to class quinoxaline, and the molecular formula is C9H5N3, Electric Literature of 23088-24-6.

Referemce:
Quinoxaline – Wikipedia,
Quinoxaline | C8H6N2 | ChemSpider

Xu, Xinyu; Chen, Kezhi published the artcile< Palladium-catalyzed C-H activation of anisole with electron-deficient auxiliary ligands: a mechanistic investigation>, Category: quinoxaline, the main research area is anisole iodobenzene arylation mechanism PES Hammett constant.

Palladium-catalyzed selective C-H activation-functionalization has shown its significance in organic transformations. Recently, Yu et al. reported a palladium-norbornene co-catalyzed meta-selective arylation of electron-rich arenes. Although the exptl. observed site-selectivity has been successfully explained by the computational work of Dongju Zhang and co-workers, some important exptl. factors, such as the ligand choice and narrow substrate scope, remain unrationalized. In contrast to what has been suggested by Dongju Zhang, we proposed the palladium-silver dinuclear species as reactive intermediates in this work. The substituent effect was estimated to unravel the e-CMD nature of the rate-determining C-H activation step. Based on this realization, the exptl. observed substrate scope and ligand choice have also been rationalized.

Organic & Biomolecular Chemistry published new progress about Arylation catalysts. 23088-24-6 belongs to class quinoxaline, and the molecular formula is C9H5N3, Category: quinoxaline.

Referemce:
Quinoxaline – Wikipedia,
Quinoxaline | C8H6N2 | ChemSpider

Makaravage, Katarina J.; Shao, Xia; Brooks, Allen F.; Yang, Lingyun; Sanford, Melanie S.; Scott, Peter J. H. published the artcile< Copper(II)-Mediated [11C]Cyanation of Arylboronic Acids and Arylstannanes>, Formula: C9H5N3, the main research area is arylboronic acid cyanation copper; arylnitrile preparation; copper radiocyanation cyanation catalyst.

A copper-mediated method for the transformation of diverse arylboron compounds and arylstannanes to aryl-[11C]-nitriles is reported. This method is operationally simple, uses com. available reagents, and is compatible with a wide variety of substituted aryl- and heteroaryl substrates. This method is applied to the automated synthesis of high specific activity [11C]perampanel in 10% nondecay-corrected radiochem. yield (RCY).

Organic Letters published new progress about Arylboronic acids Role: RCT (Reactant), RACT (Reactant or Reagent). 23088-24-6 belongs to class quinoxaline, and the molecular formula is C9H5N3, Formula: C9H5N3.

Referemce:
Quinoxaline – Wikipedia,
Quinoxaline | C8H6N2 | ChemSpider