Tag: 100-200

Electrocatalytic Minisci Acylation Reaction of N-Heteroarenes Mediated by NH₄I was written by Wang, Qing-Qing;Xu, Kun;Jiang, Yang-Ye;Liu, Yong-Guo;Sun, Bao-Guo;Zeng, Cheng-Chu. And the article was included in Organic Letters in 2017.Name: 6-Chloroquinoxaline This article mentions the following:

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. In the experiment, the researchers used many compounds, for example, 6-Chloroquinoxaline (cas: 5448-43-1Name: 6-Chloroquinoxaline).

6-Chloroquinoxaline (cas: 5448-43-1) belongs to quinoxaline derivatives. Quinoxaline is isomeric with other naphthyridines including quinazoline, phthalazine and cinnoline. Modifying quinoxaline structure it is possible to obtain a wide variety of biomedical applications, namely antimicrobial activities and chronic and metabolic diseases treatment.Name: 6-Chloroquinoxaline

Referemce:
Quinoxaline – Wikipedia,
Quinoxaline | C8H6N2 | ChemSpider

Proton resonance spectra of heterocycles. VIII. Substituent effects on coupling constants in bicyclic heteroaromatic compounds and the prediction of chemical shifts from coupling constants was written by Katritzky, A. R.;Takeuchi, Y.. And the article was included in Journal of the Chemical Society, Perkin Transactions 2: Physical Organic Chemistry (1972-1999) in 1972.Product Details of 5448-43-1 This article mentions the following:

Substituents affect coupling constants in bicyclic heteroaromatic compounds e.g., substituted 2,1,3-selenadiazole, benzofuroxan, quinazoline, quinoline; they increase 3Jαβ and 4Jαε, slightly decrease 4Jαγ and 5Jαδ, and have little effect on 3Jβγ. The regularities discussed allowed prediction of J in substituted systems. Ortho-substituent effects on chem. shifts relate to the corresponding 3J values in the unsubstituted compound, reflecting the dependence of both on partial bond fixation. In the experiment, the researchers used many compounds, for example, 6-Chloroquinoxaline (cas: 5448-43-1Product Details of 5448-43-1).

6-Chloroquinoxaline (cas: 5448-43-1) belongs to quinoxaline derivatives. Quinoxaline derivatives are important constituents of pharmacologically active compounds, including as well as for RNA synthesis inhibition, reactive dyes and pigments, azo dyes, flurox Cylin Dyes, Corrosion Inhibitors and Photovoltaic Polymers. The antitumoral properties of quinoxaline compounds have been of interest. Recently, quinoxaline and its analogs have been investigated as the catalyst’s ligands.Product Details of 5448-43-1

Referemce:
Quinoxaline – Wikipedia,
Quinoxaline | C8H6N2 | ChemSpider

Quinoxaline N-oxides. I. The oxidation of quinoxaline and its Bz-substituted derivatives was written by Landquist, Justus K.. And the article was included in Journal of the Chemical Society in 1953.Formula: C8H5ClN2 This article mentions the following:

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 In the experiment, the researchers used many compounds, for example, 6-Chloroquinoxaline (cas: 5448-43-1Formula: C8H5ClN2).

6-Chloroquinoxaline (cas: 5448-43-1) belongs to quinoxaline derivatives. Condensed heterocycles of quinoxalines have become attractive targets in synthetic and medicinal chemistry due to their significant biological activities. Quinoxaline and its analogues may also be formed by reduction of amino acids substituted 1,5-difluoro-2,4-dinitrobenzene (DFDNB),One study used 2-iodoxybenzoic acid (IBX) as a catalyst in the reaction of benzil with 1,2-diaminobenzene.Formula: C8H5ClN2

Referemce:
Quinoxaline – Wikipedia,
Quinoxaline | C8H6N2 | ChemSpider

Proton resonance spectra of heterocycles. VIII. Substituent effects on coupling constants in bicyclic heteroaromatic compounds and the prediction of chemical shifts from coupling constants was written by Katritzky, A. R.;Takeuchi, Y.. And the article was included in Journal of the Chemical Society, Perkin Transactions 2: Physical Organic Chemistry (1972-1999) in 1972.Synthetic Route of C9H8N2O This article mentions the following:

Substituents affect coupling constants in bicyclic heteroaromatic compounds e.g., substituted 2,1,3-selenadiazole, benzofuroxan, quinazoline, quinoline; they increase 3Jαβ and 4Jαε, slightly decrease 4Jαγ and 5Jαδ, and have little effect on 3Jβγ. The regularities discussed allowed prediction of J in substituted systems. Ortho-substituent effects on chem. shifts relate to the corresponding 3J values in the unsubstituted compound, reflecting the dependence of both on partial bond fixation. In the experiment, the researchers used many compounds, for example, 6-Methoxyquinoxaline (cas: 6639-82-3Synthetic Route of C9H8N2O).

6-Methoxyquinoxaline (cas: 6639-82-3) belongs to quinoxaline derivatives. Quinoxaline derivatives are important constituents of pharmacologically active compounds, including as well as for RNA synthesis inhibition, reactive dyes and pigments, azo dyes, flurox Cylin Dyes, Corrosion Inhibitors and Photovoltaic Polymers. Quinoxalines are used in the treatment of bacterial, cancer, and HIV infections. Moreover, varenicline, a clinical drug is used for treating nicotine addiction, also contains quinoxaline moiety.Synthetic Route of C9H8N2O

Referemce:
Quinoxaline – Wikipedia,
Quinoxaline | C8H6N2 | ChemSpider

Topical mosquito repellents. IX: quinolines, isoquinolines, and quinoxalines was written by Skinner, W. A.;Crawford, H. T.;Tong, H.;Skidmore, D.;Maibach, H. I.. And the article was included in Journal of Pharmaceutical Sciences in 1976.Product Details of 6639-82-3 This article mentions the following:

Various quinoxalines I, quinolines II, and isoquinolines III were evaluated for their effectiveness as topical mosquito repellents. Several tetrahydroquinolines and isoquinolines also were included. None of the compounds tested was superior to diethyltoluamide. In the experiment, the researchers used many compounds, for example, 6-Methoxyquinoxaline (cas: 6639-82-3Product Details of 6639-82-3).

6-Methoxyquinoxaline (cas: 6639-82-3) belongs to quinoxaline derivatives. Condensed heterocycles of quinoxalines have become attractive targets in synthetic and medicinal chemistry due to their significant biological activities. The antitumoral properties of quinoxaline compounds have been of interest. Recently, quinoxaline and its analogs have been investigated as the catalyst’s ligands.Product Details of 6639-82-3

Referemce:
Quinoxaline – Wikipedia,
Quinoxaline | C8H6N2 | ChemSpider

Quinoxaline N-oxides. I. The oxidation of quinoxaline and its Bz-substituted derivatives was written by Landquist, Justus K.. And the article was included in Journal of the Chemical Society in 1953.Application of 6639-82-3 This article mentions the following:

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 In the experiment, the researchers used many compounds, for example, 6-Methoxyquinoxaline (cas: 6639-82-3Application of 6639-82-3).

6-Methoxyquinoxaline (cas: 6639-82-3) belongs to quinoxaline derivatives. Quinoxaline derivatives are important constituents of pharmacologically active compounds, including antibacterial, antibiotic and antineoplastic, antifungal, anti-inflammatory and analgesic drugs. They are well-known for application in organic light emitting devices, polymers and pharmaceutical agents. The quinoxaline-containing polymers are applicable in optical devices due to their thermal stability and low band gap.Application of 6639-82-3

Referemce:
Quinoxaline – Wikipedia,
Quinoxaline | C8H6N2 | ChemSpider

1,2-Ethylenediols of quinoxaline and 1-phenyl-pyrazolo[o,4-b]quinoxaline was written by Binte, Hans J.;Henseke, Guenter;Bauer, Werner;Koehnke, Kurt. And the article was included in Zeitschrift fuer Chemie in 1968.Application of 5448-43-1 This article mentions the following:

Quinoxaloin (I) was acylated with Ac2O in pyridine to the diacetate, m. 232°, and with BzCl to the dibenzoate, m. 240°. Quinoxaloin diacetate was also obtained directly from quinoxaline-2-carboxaldehyde with Ac2O in pyridine at room temperature I was dehydrated by treatment with air in HCONMe2 to give quinoxalil, m. 248°. Oxidation of I with concentrated HNO3 gave quinoxaline-2-carboxylic acid, m. 212°. Quinoxalil condensed with o-H2NC6H4NH2 in CHCl3 to give 2,3-di(2-quinoxalyl)quinoxaline, m. 231°. R-substituted-quinoxaline-2-carboxaldehydes (II) reacted with KCN in 60% EtOH to give the following R-substituted quinoxaloins (R and m.p. given): 6- or 7-NO2, 297°; 6- or 7-Cl, 290-2°; 6-Cl, 295°; 7-Cl, 292°. II were prepared by HIO4 cleavage of the corresponding R-substituted 2-(D-arabino-tetrahydroxybutyl)quinoxaline. II (R = 6-Cl) formed a yellow phenylhydrazone, m. 197°, while II (R = 6- or 7-NO2) formed a red phenylhydrazone, m. 220-2°. 6(7)-Chloroquinoxaloin gave 6(7), 6′(7)-dichloroquinoxalyl, m. 321-3°, on oxidation with air and 6(7)-chloroquinoxaline-2-carboxylic acid, m. 241°, with HNO3. 7,7′-Dichloro-1,1′-diphenylflavazoin (III), m. 275°, was also prepared; diacetate m. 335-40°; dibenzoate m. 355-60°. It is also dehydrated with air to give isomeric flavazils, m. 300 and 334°. 1,1′-Diphenylflavazoin formed a bis(phenylhydrazone), m. 160°, while the flavazil (m. 300°) formed a monophenylhydrazone, m. 195-8°. The flavazil (m. 300°) reacted with o-H2NC6H4NH2 to give 2,3-bis(1-phenylpyrazolo[3,4-b]quinoxal-3-yl)quinoxaline, m. 283°. Tollens reagent is slowly reduced by I, II, and 1,1′-diphenylflavazoin, while Tillman reagent is reduced almost instantly in acid medium, but not in alk. medium. In the experiment, the researchers used many compounds, for example, 6-Chloroquinoxaline (cas: 5448-43-1Application of 5448-43-1).

6-Chloroquinoxaline (cas: 5448-43-1) belongs to quinoxaline derivatives. Quinoxaline is isomeric with other naphthyridines including quinazoline, phthalazine and cinnoline. Modifying quinoxaline structure it is possible to obtain a wide variety of biomedical applications, namely antimicrobial activities and chronic and metabolic diseases treatment.Application of 5448-43-1

Referemce:
Quinoxaline – Wikipedia,
Quinoxaline | C8H6N2 | ChemSpider

Thiazolo[5,4-f]quinoxalines, Oxazolo[5,4-f]quinoxalines and Pyrazino[b,e]isatins: Synthesis from 6-Aminoquinoxalines and Properties was written by Lassagne, Frederic;Sims, Joshua M.;Erb, William;Mongin, Olivier;Richy, Nicolas;El Osmani, Nour;Fajloun, Ziad;Picot, Laurent;Thiery, Valerie;Robert, Thomas;Bach, Stephane;Dorcet, Vincent;Roisnel, Thierry;Mongin, Florence. And the article was included in European Journal of Organic Chemistry in 2021.Name: 3-Chloroquinoxalin-6-amine This article mentions the following:

The regioselective iodination of different 2-mono-, 3-mono- and 2,3-disubstituted 6-aminoquinoxalines, which took place at their 5-position, was rationalized on the basis of Hueckel theory calculations Oxazolo- and thiazolo[5,4-f]quinoxaline analogs of reported disease-related protein kinases inhibitors were synthesized from the obtained 6-amino-5-iodoquinoxalines by using as key step copper-catalyzed azole ring formation. Pyrazino[b,e]isatins were obtained, for the first time, from the same substrates by recourse to Sonogashira coupling, alkyne hydration, and oxidative cyclization. The absorption and emission properties of the most promising compounds were recorded. In addition, most of the synthesized polycycles were evaluated as protein kinase inhibitors and for their antiproliferative activity towards cancer cells. In the experiment, the researchers used many compounds, for example, 3-Chloroquinoxalin-6-amine (cas: 166402-16-0Name: 3-Chloroquinoxalin-6-amine).

3-Chloroquinoxalin-6-amine (cas: 166402-16-0) belongs to quinoxaline derivatives. Quinoxaline is isomeric with other naphthyridines including quinazoline, phthalazine and cinnoline. The antitumoral properties of quinoxaline compounds have been of interest. Recently, quinoxaline and its analogs have been investigated as the catalyst’s ligands.Name: 3-Chloroquinoxalin-6-amine

Referemce:
Quinoxaline – Wikipedia,
Quinoxaline | C8H6N2 | ChemSpider

Nickel-Catalyzed C-N Cross-Coupling of Ammonia, (Hetero)anilines, and Indoles with Activated (Hetero)aryl Chlorides Enabled by Ligand Design was written by McGuire, Ryan T.;Paffile, Julia F. J.;Zhou, Yuqiao;Stradiotto, Mark. And the article was included in ACS Catalysis in 2019.Formula: C8H5ClN2 This article mentions the following:

The Ni(II) precatalyst (C1) featuring the phosphonite ancillary ligand Phen-DalPhos (L1) was employed in the cross-coupling of (hetero)anilines with (hetero)aryl chlorides and in the diarylation of ammonia with (hetero)aryl chlorides to afford heteroatom-dense di(hetero)arylamines. The PAd2-DalPhos precatalyst C4 provided complementary reactivity in cross-couplings of indoles with (hetero)aryl chlorides. Taken together, the demonstration of room-temperature reactivity within each of the reaction classes examined and the observation of useful chemoselectivity at low loading (≤0.5 mol % Ni) and on gram-scale distinguishes C1 and C4 from other metal catalysts (i.e., copper, palladium, nickel, or other) within the field of C-N cross-coupling chem. In the experiment, the researchers used many compounds, for example, 6-Chloroquinoxaline (cas: 5448-43-1Formula: C8H5ClN2).

6-Chloroquinoxaline (cas: 5448-43-1) belongs to quinoxaline derivatives. Condensed heterocycles of quinoxalines have become attractive targets in synthetic and medicinal chemistry due to their significant biological activities. Quinoxaline-1,4-di-N-oxide derivatives have shown to improve the biological results and are endowed with anti-viral, anti-cancer, anti-bacterial, and anti-protozoal activities with application in many other therapeutic areas.Formula: C8H5ClN2

Referemce:
Quinoxaline – Wikipedia,
Quinoxaline | C8H6N2 | ChemSpider

Rhodium-catalyzed transfer hydrogenation of quinoxalines with water as a hydrogen source was written by Zhang, Xia;Chen, Jingchao;Khan, Ruhima;Shen, Guoli;He, Zhenxiu;Zhou, Yongyun;Fan, Baomin. And the article was included in Organic & Biomolecular Chemistry.SDS of cas: 5448-43-1 This article mentions the following:

Rhodium-catalyzed transfer hydrogenation of quinoxalines with water as a hydrogen source is reported. The reaction allows the simple preparation of 1,2,3,4-tetrahydroquinoxalines under mild conditions. The deuterium-labeling experiment confirmed that water is the sole hydrogen source in the transfer hydrogenation reaction. In the experiment, the researchers used many compounds, for example, 6-Chloroquinoxaline (cas: 5448-43-1SDS of cas: 5448-43-1).

6-Chloroquinoxaline (cas: 5448-43-1) belongs to quinoxaline derivatives. Quinoxaline derivatives are important constituents of pharmacologically active compounds, including as well as for RNA synthesis inhibition, reactive dyes and pigments, azo dyes, flurox Cylin Dyes, Corrosion Inhibitors and Photovoltaic Polymers. They are well-known for application in organic light emitting devices, polymers and pharmaceutical agents. The quinoxaline-containing polymers are applicable in optical devices due to their thermal stability and low band gap.SDS of cas: 5448-43-1

Referemce:
Quinoxaline – Wikipedia,
Quinoxaline | C8H6N2 | ChemSpider