Day: February 9, 2023

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

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

Synthesis of 2-(Quinoxalin-2-ylamino-benzotriazolyl) Pentanedioic Derivatives as Potential Anti-Folate Agents was written by Briguglio, I.;Piras, S.;Corona, P.;Pirisi, M. A.;Burrai, L.;Boatto, G.;Gavini, E.;Rassu, G.. And the article was included in Journal of Heterocyclic Chemistry in 2016.Reference of 49679-45-0 This article mentions the following:

The chem. properties of quinoxalines and quinoxaline 1,4-dioxides with those of benzotriazole nucleus were combined with the aim to evaluate the resulting biol. properties. Two main new series, including more than 60 compounds, were prepared In the first one, the benzotriazole moiety was linked through the nitrogen atoms 1, 2, or 3, to a glutaric acid substituent to simulate a glutamic moiety. In the second series, the glutaric acid was substituted with acetic acid moiety to evaluate the effects of steric hindrance. Here, we described the multistep chem. processes to obtain all titled quinoxalines starting from com. available diamines. The classical oxidation of selected quinoxalines was unsuccessful and an independent synthetic pathway was explored to obtain new derivatives linked to the benzotriazole moieties starting from synthons bearing N-oxide functionality. In the experiment, the researchers used many compounds, for example, Ethyl 3-chloroquinoxaline-2-carboxylate (cas: 49679-45-0Reference of 49679-45-0).

Ethyl 3-chloroquinoxaline-2-carboxylate (cas: 49679-45-0) 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.Reference of 49679-45-0

Referemce:
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

Referemce:
Quinoxaline – Wikipedia,
Quinoxaline | C8H6N2 | ChemSpider

A theoretical study of a family of new quinoxaline derivatives was written by Pis Diez, Reinaldo;Duchowicz, Pablo R.;Castaneta, Heriberto;Castro, Eduardo A.;Fernandez, Francisco M.;Albesa, Alberto G.. And the article was included in Journal of Molecular Graphics & Modelling in 2006.SDS of cas: 49679-45-0 This article mentions the following:

Hybrid d. functional calculations are performed on a series of 21 new quinoxaline derivatives, which would likely exhibit important biol. activities. Optimized geometries, harmonic vibrational frequencies, and ¹H chem. shifts are reported and compared with exptl. data when available. In addition, m.ps. of 75 derivatives are predicted resorting to the quant. structure-property relationship (QSPR) theory, doing the variable selection by means of the replacement method and using 875 theor. descriptors obtained from Dragon 5 software. The best relationship found has seven descriptors with R = 0.8818 and R_l-10%-o = 0.7705. In the experiment, the researchers used many compounds, for example, Ethyl 3-chloroquinoxaline-2-carboxylate (cas: 49679-45-0SDS of cas: 49679-45-0).

Ethyl 3-chloroquinoxaline-2-carboxylate (cas: 49679-45-0) belongs to quinoxaline derivatives. Quinoxalines are important class of heterocyclic compounds, associated with wider pharmacological applications. 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: 49679-45-0

Referemce:
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

Referemce:
Quinoxaline – Wikipedia,
Quinoxaline | C8H6N2 | ChemSpider

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

Referemce:
Quinoxaline – Wikipedia,
Quinoxaline | C8H6N2 | ChemSpider

The aromaticity of substituted diazanaphthalenes was written by Guemues, Selcuk. And the article was included in Computational & Theoretical Chemistry in 2011.Category: quinoxaline This article mentions the following:

Substituted (F, Cl, OH) diazanaphthalene derivatives were considered theor. to obtain information about their stabilities and aromaticities. The expected decrease of aromaticity of naphthalene itself by double aza substitution was compensated by substitution of one of the hydrogens of the system by an electroneg. atom. The position of the substituent is strongly effective on the aromaticity of the structure such that, the aromaticity is enhanced when the substituent is closer to the aza points. 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. 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.Category: quinoxaline

Referemce:
Quinoxaline – Wikipedia,
Quinoxaline | C8H6N2 | ChemSpider

Exploiting Ancillary Ligation To Enable Nickel-Catalyzed C-O Cross-Couplings of Aryl Electrophiles with Aliphatic Alcohols was written by MacQueen, Preston M.;Tassone, Joseph P.;Diaz, Carlos;Stradiotto, Mark. And the article was included in Journal of the American Chemical Society in 2018.SDS of cas: 5448-43-1 This article mentions the following:

The use of (L)Ni(o-tolyl)Cl precatalysts (L = PAd-DalPhos or CyPAd-DalPhos, I or II, resp.) enables the C(sp²)-O cross-coupling of primary, secondary, or tertiary aliphatic alcs. with (hetero)aryl electrophiles, including unprecedented examples of such nickel-catalyzed transformations employing (hetero)aryl chlorides, sulfonates, and pivalates. In addition to offering a competitive alternative to palladium catalysis, this work establishes the feasibility of utilizing ancillary ligation as a complementary means of promoting challenging nickel-catalyzed C(sp²)-O cross-couplings, without recourse to precious-metal photoredox catalytic methods. 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 antibacterial, antibiotic and antineoplastic, antifungal, anti-inflammatory and analgesic drugs. 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.SDS of cas: 5448-43-1

Referemce:
Quinoxaline – Wikipedia,
Quinoxaline | C8H6N2 | ChemSpider

A novel synthesis of quinoxaline-6-carbaldehyde and its evaluation as potential antimicrobial agent was written by Pai, Nandini R.;Vishwasrao, Sandesh G.. And the article was included in Pharma Chemica in 2011.Recommanded Product: 5448-43-1 This article mentions the following:

A novel synthetic process for quinoxaline-6-carboxaldehyde (I), expected to exhibit antimicrobial activity, was presented. Compound I was evaluated for antimicrobial potency in vitro and in vivo. The min. inhibitory concentration (MIC) of the I against bacteria was determined by agar and broth dilution in vitro. The antibacterial activity was confirmed by animal experiments Toxicity and protective efficacy were tested in vivo. Compound I inhibited most of the bacterial isolates at 25-100 μg/mL, and a few were sensitive even at 10 μg/mL. It was found to be bacteriostatic against Shigella dysenteriae and bactericidal against S. aureus. When administered to mice, I protected the animals challenged with 50 MLD of Salmonella typhimurium. The drug showed inhibitory action against several pathogenic bacteria and also offered significant protection to mice against the bacterial challenge. 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 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.Recommanded Product: 5448-43-1

Referemce:
Quinoxaline – Wikipedia,
Quinoxaline | C8H6N2 | ChemSpider