Category: 6639-82-3

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.Formula: C9H8N2O 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-Methoxyquinoxaline (cas: 6639-82-3Formula: C9H8N2O).

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. Modifying quinoxaline structure it is possible to obtain a wide variety of biomedical applications, namely antimicrobial activities and chronic and metabolic diseases treatment.Formula: C9H8N2O

Referemce:
Quinoxaline – Wikipedia,
Quinoxaline | C8H6N2 | ChemSpider

Nitration of quinoxalines was written by Otomasu, Hirotaka;Nakajima, Shoichi. And the article was included in Chemical & Pharmaceutical Bulletin in 1958.Product Details of 6639-82-3 This article mentions the following:

Quinoxaline (I), its N-oxide, and its 2,3-Me₂ derivative resisted nitration even with concentrated H₂SO₄ and fuming HNO₃ (d. 1.52) at 100°. The presence of polar substituents in either ring facilitated nitration. The 6-MeO derivative (II) of I (0.43 g.) in 4 cc. concentrated H₂SO₄ at 0°, well stirred during the addition of 0.5 g. powd. KNO₃, the mixture kept 2 hrs. at room temperature, and poured on ice yielded 0.45 g. 5,6-O₂N(MeO) derivative (III) of I, m. 203° (Me₂CO), and this catalytically reduced (10% Pd-C) in MeOH gave the 5,6-H₂N(MeO) derivative (IV) of I, m. 96° (ligroine). The position of the NO₂ group in III was confirmed by the synthesis of IV from 4,2,3-H₂N(O₂N)₂C₆H₂OMe (V). V (5 g.) catalytically reduced (Pd-C) to 2,3,4-(H₂N)₃C₆H₂OMe, and this under H warmed 30 min. with 10 g. glyoxal bisulfite in 200 cc. hot H₂O, the mixture refluxed 1.5 hrs. on a water bath, evaporated in vacuo, made alk. with NaOH, and the resulting solid extracted with CHCl₃ yielded 1.2 g. IV, identical with the sample from III. No isomeric 5,8-H₂N(MeO) derivative (VI) of I was produced in this reaction. However, 4 g. 4,2,3-AcNH(O₂N)₂C₆H₂OMe in place of V similarly reduced and condensed with (CHO)₂ yielded 1.8 g. 5,8-AcNH(MeO) derivative of I, m. 149°, hydrolyzed by warming 1 hr. on a water bath with 20% NaOH and extracting the cooled mixture with CHCl₃ to give VI, m. 125° (C₆H₆). The 5-MeO derivative of I (0.5 g.) in 5 cc. concentrated H₂SO₄ warmed 15 min. at 60° with 1 g. KNO₃ and the mixture poured into 80 cc. ice water yielded 0.6 g. 5,6,8-MeO(O₂N)₂ derivative of I, m. 204-6° (MeOH), and no mono-O₂N derivative could be formed even at a lower temperature 3,2-Me(HO) derivative of I (5 g.) nitrated as was II yielded 5 g. 3,2,6-Me(HO)(O₂N) derivative (VII) of I, m. 270° (Me₂CO), but no nitration of the 2,3-Cl(Me) or 2,3-(EtO)Me derivatives of I took place under similar conditions. In an attempt to confirm the position of the NO₂ group in VII by synthesis, 1.5 g. 3,4-(H₂N)₂C₆H₃NO₂ (VIII) in 200 cc. MeOH was boiled 1 hr. with 1 g. AcCO₂H and the MeOH evaporated to yield 1.85 g. 3,2,7-Me(HO)(O₂N) derivative of I, m. 255° (MeOH), obviously different from VII. VII (1 g.) methylated with 4 cc. Me₂SO₄ in 20 cc. 20% NaOH yielded 0.55 g. 1,3-dimethyl-2-oxo-6-nitro-1,2-dihydroquinoxaline, m. 218° (Me₂CO), formed also (0.16 g.) from 0.2 g. 2,4-H₂N(O₂N)C₆H₃NHMe in 50 cc. MeOH condensed as was VIII with 0.2 g. AcCO₂H. This synthesis confirms the 6-position of NO₂ in VII. 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. Quinoxaline derivatives are important constituents of pharmacologically active compounds, including antibacterial, antibiotic and antineoplastic, antifungal, anti-inflammatory and analgesic drugs. The parent substance of the group, quinoxaline, results when glyoxal is condensed with 1,2-diaminobenzene. Substituted derivatives arise when α-ketonic acids, α-chlorketones, α-aldehyde alcohols and α-ketone alcohols are used in place of diketones.Product Details of 6639-82-3

Referemce:
Quinoxaline – Wikipedia,
Quinoxaline | C8H6N2 | ChemSpider

Selective skeletal editing of polycyclic arenes using organophotoredox dearomative functionalization was written by Ji, Peng;Davies, Cassondra C.;Gao, Feng;Chen, Jing;Meng, Xiang;Houk, Kendall N.;Chen, Shuming;Wang, Wei. And the article was included in Nature Communications in 2022.Reference of 6639-82-3 This article mentions the following:

A general organophotoredox approach for the chemo- and regioselective dearomatization of structurally diverse polycyclic aromatics, including quinolines, isoquinolines, quinoxalines, naphthalenes, anthracenes and phenanthrenes was described. The success of the method for chemoselective oxidative rupture of aromatic moieties relies on precise manipulation of the electronic nature of the fused polycyclic arenes. Mechanistic studies show that the addition of a hydrogen atom transfer (HAT) agent helps favor the dearomatization pathway over the more thermodynamically downhill aromatization pathway. This strategy was applied to rapid synthesis of biol. valued targets and late-stage skeletal remodeling en route to complex structures. In the experiment, the researchers used many compounds, for example, 6-Methoxyquinoxaline (cas: 6639-82-3Reference of 6639-82-3).

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. 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.Reference of 6639-82-3

Referemce:
Quinoxaline – Wikipedia,
Quinoxaline | C8H6N2 | ChemSpider

Studies on the thalleioquine reaction was written by Takada, Atsushi;Negishi, Haruo;Ueda, Takeo. And the article was included in Chemical & Pharmaceutical Bulletin in 1983.Application of 6639-82-3 This article mentions the following:

Two colored substances produced in the thalleioquine reaction using 6-methoxyquinoxaline as a model compound were isolated. The red substance was determined to be an 8,8′-biquinolinyl derivative (I), and the blue substance was found to be a super-stable radical compound 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. Condensed heterocycles of quinoxalines have become attractive targets in synthetic and medicinal chemistry due to their significant biological activities. The parent substance of the group, quinoxaline, results when glyoxal is condensed with 1,2-diaminobenzene. Substituted derivatives arise when α-ketonic acids, α-chlorketones, α-aldehyde alcohols and α-ketone alcohols are used in place of diketones.Application of 6639-82-3

Referemce:
Quinoxaline – Wikipedia,
Quinoxaline | C8H6N2 | ChemSpider

Study of heterocyclic quinones. XXVII. Catalysis by copper ions of the reaction of quinoxaline-5,8-quinones with amines was written by Chernyak, S. A.;Tsizin, Yu. S.. And the article was included in Khimiya Geterotsiklicheskikh Soedinenii in 1976.Product Details of 6639-82-3 This article mentions the following:

Aminomethoxyquinoxaline I, prepared in 71% yield from nitroaminoanisole and N2H4.H2O by cyclization, nitration, and reduction, was oxidized by ·ON(SO3K)2 to give 65% II (R1 = OMe, R2 = H) which was aminated by morpholine and piperidine to give 86 and 78% II (R1 = morpholino, piperidino, R2 = H), resp. Addnl. obtained were 65-83% II (R1 = R2 = morpholino, piperidino; R1 = piperidino, R2 = morpholino) and 95% CuCl2 complex of II (R1 = piperidino, R2 = H). 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. 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 as dyes, pharmaceuticals, and antibiotics such as echinomycin, levomycin exhibiting antitumoral properties. Quinoxalines establish also the basis of anthelmintics and receptor antagonists.Product Details of 6639-82-3

Referemce:
Quinoxaline – Wikipedia,
Quinoxaline | C8H6N2 | ChemSpider

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.Application In Synthesis of 6-Methoxyquinoxaline 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-Methoxyquinoxaline (cas: 6639-82-3Application In Synthesis of 6-Methoxyquinoxaline).

6-Methoxyquinoxaline (cas: 6639-82-3) belongs to quinoxaline derivatives. Quinoxalines are important class of heterocyclic compounds, associated with wider pharmacological applications. The parent substance of the group, quinoxaline, results when glyoxal is condensed with 1,2-diaminobenzene. Substituted derivatives arise when α-ketonic acids, α-chlorketones, α-aldehyde alcohols and α-ketone alcohols are used in place of diketones.Application In Synthesis of 6-Methoxyquinoxaline

Referemce:
Quinoxaline – Wikipedia,
Quinoxaline | C8H6N2 | ChemSpider

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 was written by Climent, M. J.;Corma, A.;Hernandez, J. C.;Hungria, A. B.;Iborra, S.;Martinez-Silvestre, S.. And the article was included in Journal of Catalysis in 2012.Reference of 6639-82-3 This article mentions the following:

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

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-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.Reference of 6639-82-3

Referemce:
Quinoxaline – Wikipedia,
Quinoxaline | C8H6N2 | ChemSpider

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 was written by Climent, M. J.;Corma, A.;Hernandez, J. C.;Hungria, A. B.;Iborra, S.;Martinez-Silvestre, S.. And the article was included in Journal of Catalysis in 2012.Reference of 6639-82-3 This article mentions the following:

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

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-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.Reference of 6639-82-3

Referemce:
Quinoxaline – Wikipedia,
Quinoxaline | C8H6N2 | ChemSpider