Tag: 100-200

1-Alkyl-1,2,3,4-tetrahydroquinoxalines was written by Cavagnol, J. C.;Wiselogle, F. Y.. And the article was included in Journal of the American Chemical Society in 1947.COA of Formula: C8H5ClN2 This article mentions the following:

3,4-(H₂N)₂C₆H₃Me results in 86.5% yield on reduction of 3,4-O₂N(H₂N)C₆H₃Me over Raney Ni and 3,4-(H₂N)₂C₆H₃OMe in 86% yield, from 3,4-O₂N(H₂N)C₆H₃OMe. o-C₆H₄(NH₂)₂ (108.1 g.) in 500 cc. 2 M AcOH and 250 cc. 4 M AcONa at 60°, poured rapidly into 298.4 g. (CHO)₂.2NaHSO₃.H₂O in 1500 cc. H₂O at 60°, the solution stirred 1 hr., cooled to below 10°, neutralized with 120 g. NaOH, 500 g. K₂CO₃ added, the oily amine extracted with one 500-cc. portion of C₆H₆, and the solution extracted 8 hrs. with 300 cc. C₆H₆, gives 85% quinoxaline (I), b₁ 44-5°, b₁₀ 96°, b₃₁ 124°, b₇₆₀ 225°, m. 30.5-1.5°; 6-Cl derivative b₁₀ 117-19°, m. 63.8-4.3°, 79%; 6-Me derivative b₁ 86°, b₂₉ 141.5°, m. below 0°, 86%; 6-MeO derivative b₇ 128°, m. 60°, 88%. I (130.1 g.) in 1200 cc. C₆H₆, shaken with 10 cc. moist Raney Ni to remove catalyst poisons, and then reduced over 1.5 g. Pt oxide at 50-80 lb. pressure, give 92% 1,2,3,4-tetrahydroquinoxaline (II), m. 98.5-9° (HCl salt, m. 167-9°); 6-Cl derivative m. 113-14°; 6-Me derivative m. 104.5-5.5°, 92%; 6-MeO derivative m. 80.5-1°, 95%. A variety of methods for the monoalkylation of II failed. II (40.3 g.) in 350 cc. 20% NaOH at 20°, treated dropwise with 115 cc. PhSO₂Cl (60 drops/min.) during 2.5-3 hrs. (vigorous stirring), gives 87% 1,2,3,4-tetrahydro-1-phenylsulfonylquinoxaline (III), yellow, m. 138-9°; with C₅H₅N, 10% excess PhSO₂Cl is sufficient and the III has a red tinge. III (0.1 mole), 0.4 mole alkyl halide, 0.2 mole anhydrous Na₂CO₃, and 100 cc. 95% EtOH, refluxed 48 hrs. in a N atm., give 88-92% of 1-substituted derivatives: Me, m. 88-9° (methiodide, m. 168-9°); Et, m. 118.5-19.5°; Pr, m. 119.5-20°; iso-Pr, m. 142.5-3.5°; Bu, m. 95-5.5°; benzyl, m. 134-5°; Ac, m. 111.5-12°. Hydrolysis with concentrated H₂SO₄ gives 1-alkyl-1,2,3,4-tetrahydroquinoxalines: Me, b₂ 108.5°, 76%; Et, b₁ 88-90°, 59% (oxalate, m. 130-1°); Pr, b_1.5 113.5°, 66%; iso-Pr, b_1.5 107.5°, 68%; Bu, b₁ 107.5°, 81% (oxalate, m. 142.5-3.5°); benzyl, b_1.5 178-9°, m. 50.5-2.5°, 66%. Picrates: II, m. 128.5-9.5°; 1-Me, m. 123-6.5°; 1-Et, m. 111.5-12°; 1-Pr, m. 135-6°; 1-iso-Pr, m. 131-2°; 1-Bu, m. 130-1.5°; 1-benzyl, m. 150-1.5°; 6-MeO, m. 134-5°; 6-Me, m. 148-8.5°. Derivatives of 1-benzoyl-1,2,3,4-tetrahydroquinoxaline: 4-Me, m. 109-10°; 4-Et, m. 123-4°; 4-Pr, m. 88-9°; 4-iso-Pr, m. 114-15°; 4-Bu, m. 87-8°; 4-benzyl, m. 123.3-3.8°. 1,4-Dibenzoyl-1,2,3,4-tetrahydroquinoxalines: 6-Me, m. 141.5-2°; 6-MeO, m. 138.5-8.8°; 6-Cl, m. 168.5-9°. 1,4-Diacetyl-6-methyl-1,2,3,4-tetrahydroquinoxaline m. 105.2-6.2°. 1,4-Dicarbethoxy-1,2,3,4-tetrahydroquinoxaline, m. 42-4°; the trihydrate is an oil. 1,4-Bis (phenylsulfonyl)-6-methyl-1,2,3,4-tetrahydroquinoxaline m. 124-5°. In the experiment, the researchers used many compounds, for example, 6-Chloroquinoxaline (cas: 5448-43-1COA of Formula: C8H5ClN2).

6-Chloroquinoxaline (cas: 5448-43-1) belongs to quinoxaline derivatives. Quinoxalines have received a significant amount of attention due to their potential use in fighting various pathophysiological conditions like epilepsy, Parkinson’s, and Alzheimer’s diseases. 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.COA of Formula: C8H5ClN2

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Quinoxaline – Wikipedia,
Quinoxaline | C8H6N2 | ChemSpider

MOF-Derived Subnanometer Cobalt Catalyst for Selective C-H Oxidative Sulfonylation of Tetrahydroquinoxalines with Sodium Sulfinates was written by Xie, Feng;Lu, Guang-Peng;Xie, Rong;Chen, Qing-Hua;Jiang, Huan-Feng;Zhang, Min. And the article was included in ACS Catalysis in 2019.Category: quinoxaline This article mentions the following:

Cobalt supported on nitrogen-doped carbon was prepared by deposition of cobalt into ZIF-8 followed by pyrolysis and used as a catalyst for the aerobic oxidative sulfonylation of 1,2,3,4-tetrahydroquinoxalines with sodium sulfinates in the presence of NH₄I to yield arylsulfonylquinoxalines such as I (R = Ph, 4-MeC₆H₄, 4-MeOC₆H₄, 2-naphthyl, 2,4,6-Me₃C₆H₂, 4-FC₆H₄, 2-FC₆H₄, 4-ClC₆H₄, 4-BrC₆H₄, 4-F₃CC₆H₄, 3-pyridinyl, 2-thienyl, 8-quinolinyl, 3,5-dimethyl-4-isoxazolinyl, Me, Et, cyclopropyl). The supported cobalt catalyst was used six times with < 10% decrease in product yield. In the experiment, the researchers used many compounds, for example, 6-Chloroquinoxaline (cas: 5448-43-1Category: quinoxaline).

6-Chloroquinoxaline (cas: 5448-43-1) 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.Category: quinoxaline

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Quinoxaline – Wikipedia,
Quinoxaline | C8H6N2 | ChemSpider

Detection of glyoxal bound to protein by gas chromatography after derivatization to quinoxaline and its application for biological sample was written by Segawa, Toshiharu;Ueno, Hitoshi;Nakamuro, Katsuhiko;Sayato, Yasuyoshi. And the article was included in Japanese Journal of Toxicology and Environmental Health in 1992.SDS of cas: 5448-43-1 This article mentions the following:

The microdetermination method for glyoxal bound to proteins in biol. samples has been developed using GC with an electron capture detector. The treatment of the glyoxal-bound protein with 4-chloro-o-phenylenediamine gave its derivative, 6-chloroquinoxaline, showing the release of glyoxal from the protein. The use of metaphosphoric acid as a precipitant of the protein was suitable. The results from Sephadex G-25 gel chromatog. coupled with this microdetermination method indicated that glyoxal binds to bovine albumin. The amounts of glyoxal bound to the albumin, fetal bovine serum, and rat liver homogenate increased with an increase of glyoxal added. 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. Quinoxalines have received a significant amount of attention due to their potential use in fighting various pathophysiological conditions like epilepsy, Parkinson’s, and Alzheimer’s diseases. Modifying quinoxaline structure it is possible to obtain a wide variety of biomedical applications, namely antimicrobial activities and chronic and metabolic diseases treatment.SDS of cas: 5448-43-1

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Quinoxaline – Wikipedia,
Quinoxaline | C8H6N2 | ChemSpider

Synthesis and characterization of new rhodamine dyes with large Stokes shift was written by Tian, Zhidan;Tian, Baozhu;Zhang, Jinlong. And the article was included in Dyes and Pigments in 2013.Safety of 6-Methoxyquinoxaline This article mentions the following:

Two new rhodamine dyes (Rh Q-H, Rh Q-Me) containing 1, 4-diethyl-1, 2, 3, 4-tetrahydroquinoxaline as an effective electron donor are designed and synthesized. The structures of the novel compounds are confirmed by ¹H NMR, ¹³C NMR and ESI. Due to an excited-state intramol. charge transfer (ICT), the new dyes exhibit longer absorption (>580 nm) and emission (>640 nm) compared with the model compounds, rhodamine 101 and rhodamine 6G. The new rhodamine dyes show large Stokes shift of 40-50 nm in commonly used solvents. Notably, when measured in a mixture of H₂O/EtOH solution, significant stokes shift of 65-68 nm are achieved, which is among the largest Stokes shifts ever reported for rhodamine dyes. In the experiment, the researchers used many compounds, for example, 6-Methoxyquinoxaline (cas: 6639-82-3Safety of 6-Methoxyquinoxaline).

6-Methoxyquinoxaline (cas: 6639-82-3) belongs to quinoxaline derivatives. Compounds possessing quinoxaline derivatives were bestowed with a variety of significant biological properties such as antiviral, antimalarial, anticancer, DNA intercalation, DNA duplex stabilization, and many others. Quinoxalines are used as dyes, pharmaceuticals, and antibiotics such as echinomycin, levomycin exhibiting antitumoral properties. Quinoxalines establish also the basis of anthelmintics and receptor antagonists.Safety of 6-Methoxyquinoxaline

Referemce:
Quinoxaline – Wikipedia,
Quinoxaline | C8H6N2 | ChemSpider

Hydroxyquinoxalines and -phenazines and experiments on the preparation of hydroxyquinoxaline di-N-oxides was written by King, F. E.;Clark, N. G.;Davis, P. M. H.. And the article was included in Journal of the Chemical Society in 1949.Application of 6639-82-3 This article mentions the following:

6,7-Dimethoxyquinoxaline (I) (1 g.) and 3 g. AlCl₃ in 20 cc. C₆H₆, refluxed 15 hrs., give 82% 6,7-dihydroxyquinoxaline, m. about 260° (decomposition); di-Ac derivative, buff, m. 112°. 6-Methoxyquinoxaline (II) yields 37% of the 6-HO compound (III), m. 242° (decomposition); acetate, m. 80-1°. p-C₆H₄(OMe)₂ and HNO₃ in AcOH give 80% of the 2,3- and 2,5-di-NO₂ derivatives (IV); reduction in MeOH over Raney Ni at 2-3 atm., addition to (CHO)₂.NaHSO₃ (V) and a little HCl, the mixture refluxed 2 hrs., the MeOH evaporated, and the 2,5,1,4-(H₂N)₂C₆H₂(OMe)₂ removed (finally with NaNO₂), give 12% 5,8-dimethoxyquinoxaline, yellow, m. 146°; demethylation with AlCl₃ in C₆H₆ gives 60% of the 2,8-di-HO compound, orange, m. about 230°; diacetate, m. 209°. 2,3-(O₂N)₂C₆H₃OMe (2.5 g.), reduced over Raney Ni and the product refluxed 2 hrs. with 5 g. V in 30 cc. H₂O and a little HCl, gives 59% 5-methoxyquinoxaline, pale yellow, m. 72-3°; the 5-HO compound, yellow, m. 100-1° (30%); acetate, m. 103-4°. 3,4,1,2-(O₂N)₂C₆H₂(OMe)₂ similarly yields 36% 5,6-dimethoxyquinoxaline, yellow, m. 69-70°; the 5,6-di-HO compound yellow, m. about 190° (decomposition); diacetate, m. 112°. 4,5,1,3-(O₂N)₂C₆H₂(OMe)₂ yields 68% 5,7-dimethoxyquinoxaline, m. 110°; 5,7-di-HO compound, bright yellow, m. about 250° (decomposition); diacetate, m. 113°. The HO compounds can be distinguished by their color reactions with 2 N HCl, 2 N NaOH, and aqueous and alc. FeCl₃, which are given. The diamine solution from 5 g. IV and 2 g. 1,2-cyclohexanedione in 10 g. AcOH containing 5 g. AcONa gives 24% 1,4-dimethoxy-5,6,7,8-tetrahydrophenazine (VI), yellow, m. 152 °; 2 g. VI and 1 g. Pd-C, heated 1 hr. at 200-30°, give 50% 1,4-dimethoxyphenazine, blood-red, m. 185°; AlCl₃ in C₆H₆ (refluxed 16 hrs.) gives 91% 1,4-dihydroxyphenazine (VII), deep red, m. 230°; diacetate, tarnished gold, m. 193.5-4°. 3,4,1,2-(H₂N)₂C₆H₂(OMe)₂ yields 60% of the 1,2-di-MeO isomer of VI, m. 82-3° [picrate, yellowish brown, m. 128° (decomposition)]; 4,5,1,3-(O₂N)₂C₆H₂(OMe)₂ yields 94% of the 1,3-isomer, yellow needles from aqueous EtOH; 2,3-isomer (VIII) (88% from 4,5,1,2-(H₂N)₂C₆H₂(OMe)₂), lemon-yellow, m. 119-20°; the 1,3- and 2,3-isomers could not be dehydrogenated. 2,3-H₂N (p-MeC₆H₄N:N)C₆H₃Me (2 g.) and 20 cc. cyclohexanone, refluxed 2 hrs. with 1 drop concentrated HCl, give 45% 2-methyl-5,6,7,8-tetrahydrophenazine, yellow, m. 81°. I (1 g.) in 25 cc. AcOH, heated 20 hrs. at 60° with 5 cc. 100-volume H₂O₂, gives 60% of the 1,4-dioxide, pale yellow, decomposing about 250°; 1,4-dioxide of II, pale yellow, m. 207-10° (decomposition), 42%; of III, yellow, m. 245° (decomposition), 33%; 9,10-dioxide of VIII, pale yellow, decompose 215-20°, 66%. VII is not identical with the phenazine obtained by the reduction of iodinin (C.A. 32, 5402.6). 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. Quinoxalines are important class of heterocyclic compounds, associated with wider pharmacological applications. The antitumoral properties of quinoxaline compounds have been of interest. Recently, quinoxaline and its analogs have been investigated as the catalyst’s ligands.Application of 6639-82-3

Referemce:
Quinoxaline – Wikipedia,
Quinoxaline | C8H6N2 | ChemSpider

Iodine-alcohol molecular complexes was written by Derwish, Ghazi A. W.. And the article was included in Proc. Intern. Symp. Mol. Struct. Spectry., Tokyo in 1962.SDS of cas: 6639-82-3 This article mentions the following:

The absorption spectra of I in 12 aliphatic n-, sec-, tert-, and iso-alcs. show bands at about 455, 360, 290, and 220 mμ. The band at ∼455 mμ is shifted ∼450 cm.-1 to higher wavelengths in comparison to the ternary systems, I-alc.-inert solvent, while its intensity is enhanced. This is probably due to a solvation of the I-alc. complex by the polar alc. mols. Frequency and extinction of the band at 220230 mμ increase with increasing ionization potential of the corresponding alc., and the frequency is much higher than in the ternary systems involving inert solvents. These differences may be due to different extents of H bonding. The bands at ∼360 and ∼290 mμ, appearing after a few hrs. standing, are ascribed to I₃^–. In the experiment, the researchers used many compounds, for example, 6-Methoxyquinoxaline (cas: 6639-82-3SDS of cas: 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. 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.SDS of cas: 6639-82-3

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Quinoxaline – Wikipedia,
Quinoxaline | C8H6N2 | ChemSpider

Nickel-catalyzed dehydrogenative coupling of aromatic diamines with alcohols: selective synthesis of substituted benzimidazoles and quinoxalines was written by Bera, Atanu;Sk, Motahar;Singh, Khushboo;Banerjee, Debasis. And the article was included in Chemical Communications (Cambridge, United Kingdom) in 2019.Application In Synthesis of 6-Methoxyquinoxaline This article mentions the following:

The first nickel-catalyzed dehydrogenative coupling of primary alcs. and ethylene glycol with aromatic diamines for selective synthesis of mono- and di-substituted benzimidazoles and quinoxalines is reported. The earth-abundant, non-precious and simple NiCl₂/1,10-phenanthroline system enables the synthesis of N-heterocycles releasing water and hydrogen gas as byproducts. Mechanistic studies involving deuterium labeling experiments and quant. determination of hydrogen gas evaluation were performed. In the experiment, the researchers used many compounds, for example, 6-Methoxyquinoxaline (cas: 6639-82-3Application In Synthesis of 6-Methoxyquinoxaline).

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. 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.Application In Synthesis of 6-Methoxyquinoxaline

Referemce:
Quinoxaline – Wikipedia,
Quinoxaline | C8H6N2 | ChemSpider

CuI/Oxalic Diamide Catalyzed Coupling Reaction of (Hetero)Aryl Chlorides and Amines was written by Zhou, Wei;Fan, Mengyang;Yin, Junli;Jiang, Yongwen;Ma, Dawei. And the article was included in Journal of the American Chemical Society in 2015.Recommanded Product: 5448-43-1 This article mentions the following:

A class of oxalic diamides are found to be effective ligands for promoting CuI-catalyzed aryl amination with less reactive (hetero)aryl chlorides. The reaction proceeds at 120 °C with K₃PO₄ as the base in DMSO to afford a wide range of (hetero)aryl amines in good to excellent yields. The bis(N-aryl) substituted oxalamides are superior ligands to N-aryl-N’-alkyl substituted or bis(N-alkyl) substituted oxalamides. Both the electronic nature and the steric property of the aromatic rings in ligands are important for their efficiency. In the experiment, the researchers used many compounds, for example, 6-Chloroquinoxaline (cas: 5448-43-1Recommanded Product: 5448-43-1).

6-Chloroquinoxaline (cas: 5448-43-1) belongs to quinoxaline derivatives. Quinoxaline derivatives are important constituents of pharmacologically active compounds, including antibacterial, antibiotic and antineoplastic, antifungal, anti-inflammatory and analgesic drugs. The antitumoral properties of quinoxaline compounds have been of interest. Recently, quinoxaline and its analogs have been investigated as the catalyst’s ligands.Recommanded Product: 5448-43-1

Referemce:
Quinoxaline – Wikipedia,
Quinoxaline | C8H6N2 | ChemSpider

Ruthenium(II) η⁶-arene complexes containing a dinucleating ligand based on 1,8-naphthyridine was written by Tang, Wei-Hung;Liu, Yi-Hung;Peng, Shie-Ming;Liu, Shiuh-Tzung. And the article was included in Journal of Organometallic Chemistry in 2015.Reference of 5448-43-1 This article mentions the following:

Ruthenium arene half-sandwich complexes, [(η⁶-p-cymene)₂Ru₂(μ-L)Cl₂](PF₆)₂ (3b, L = N,N,N’,N’-tetra-2-pyridinyl-1,8-naphthyridine-2,7-diamine) and [(η⁶-p-cymene)Ru(L’)Cl](PF₆) [4, L’ = tri-2-pyridinylamine], were synthesized and characterized by spectroscopic and anal. techniques. The mol. structure of [(η⁶-p-cymene)₂Ru₂(μ-L)Cl₂]Cl₂ (3a) was further determined by single-crystal x-ray anal. The use of these ruthenium complexes as pre-catalysts for oxidative coupling of 1,2-diols/1,2-aminoalc. with o-phenylenediamines leading to quinoxalines was investigated. Complex 3b appeared to be a good catalyst for this transformation. In the experiment, the researchers used many compounds, for example, 6-Chloroquinoxaline (cas: 5448-43-1Reference of 5448-43-1).

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. Quinoxalines are used as dyes, pharmaceuticals, and antibiotics such as echinomycin, levomycin exhibiting antitumoral properties. Quinoxalines establish also the basis of anthelmintics and receptor antagonists.Reference of 5448-43-1

Referemce:
Quinoxaline – Wikipedia,
Quinoxaline | C8H6N2 | ChemSpider

New 6-Aminoquinoxaline Derivatives with Neuroprotective Effect on Dopaminergic Neurons in Cellular and Animal Parkinson Disease Models was written by Le Douaron, Gael;Ferrie, Laurent;Sepulveda-Diaz, Julia E.;Amar, Majid;Harfouche, Abha;Seon-Meniel, Blandine;Raisman-Vozari, Rita;Michel, Patrick P.;Figadere, Bruno. And the article was included in Journal of Medicinal Chemistry in 2016.Name: 3-Chloroquinoxalin-6-amine This article mentions the following:

Parkinson’s disease (PD) is a neurodegenerative disorder of aging characterized by motor symptoms that result from the loss of midbrain dopamine neurons and the disruption of dopamine-mediated neurotransmission. There is currently no curative treatment for this disorder. To discover druggable neuroprotective compounds for dopamine neurons, the authors have designed and synthesized a 2nd-generation of quinoxaline-derived mols. based on structure-activity relation studies, which led previously to the discovery of the authors’ 1st neuroprotective brain penetrant hit compound MPAQ (5c). Neuroprotection assessment in PD cellular models of the authors’ newly synthesized quinoxaline-derived compounds led to the selection of a better hit compound, PAQ (4c). Extensive in vitro characterization of 4c showed that its neuroprotective action is partially attributable to the activation of reticulum endoplasmic ryanodine receptor channels. Most interestingly, 4c was able to attenuate neurodegeneration in a mouse model of PD, making this compound an interesting drug candidate for the treatment of this disorder. 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. 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.Name: 3-Chloroquinoxalin-6-amine

Referemce:
Quinoxaline – Wikipedia,
Quinoxaline | C8H6N2 | ChemSpider