Category: quinoxaline

Direct C-H arylation of heterocycles with heteroaryl chlorides using a bis(alkoxo)palladium complex was written by Li, Yabo;Wang, Jingran;Yan, Beiqi;Huang, Mengmeng;Zhu, Yu;Wu, Yusheng;Wu, Yangjie. And the article was included in Tetrahedron in 2015.Synthetic Route of C8H5ClN2 This article mentions the following:

An efficient and practical bis(alkoxo)palladium complex Cat.I catalyzed C-H arylation of heterocycles with heteroaryl chlorides has been developed. With 1 mol % of Cat.I, the direct arylation of a series of heterocycles with various heteroaryl chlorides could proceed smoothly affording desired products in moderate to excellent yields. The catalytic system allows one-pot synthesis of 2,5-diheteroaryled thiophenes via twofold direct C-H arylation. In the experiment, the researchers used many compounds, for example, 6-Chloroquinoxaline (cas: 5448-43-1Synthetic Route of C8H5ClN2).

6-Chloroquinoxaline (cas: 5448-43-1) 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. The antitumoral properties of quinoxaline compounds have been of interest. Recently, quinoxaline and its analogs have been investigated as the catalyst’s ligands.Synthetic Route of C8H5ClN2

Referemce:
Quinoxaline – Wikipedia,
Quinoxaline | C8H6N2 | ChemSpider

A General, Practical Palladium-Catalyzed Cyanation of (Hetero)Aryl Chlorides and Bromides was written by Senecal, Todd D.;Shu, Wei;Buchwald, Stephen L.. And the article was included in Angewandte Chemie, International Edition in 2013.SDS of cas: 5448-43-1 This article mentions the following:

The authors have disclosed a general method for the cyanation of (hetero)aryl chlorides and bromides. The authors use a palladium-catalyzed cyanation system that (1) is applicable to aryl chlorides at low to moderate catalyst loadings; (2) works well with a wide range of heterocyclic halides, including in many cases five-membered heterocycles bearing free NH groups; and (3) is complete in one hour at 閳?100鎺? The use of a nontoxic cyanide source in conjunction with wide functional-group tolerance and fast reaction times make this method particularly convenient to synthetic chemists. 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 is isomeric with other naphthyridines including quinazoline, phthalazine and cinnoline. 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

Ruthenium(II) 鐣?sup>6-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.Recommanded Product: 6639-82-3 This article mentions the following:

Ruthenium arene half-sandwich complexes, [(鐣?sup>6-p-cymene)₂Ru₂(娓?L)Cl₂](PF₆)₂ (3b, L = N,N,N’,N’-tetra-2-pyridinyl-1,8-naphthyridine-2,7-diamine) and [(鐣?sup>6-p-cymene)Ru(L’)Cl](PF₆) [4, L’ = tri-2-pyridinylamine], were synthesized and characterized by spectroscopic and anal. techniques. The mol. structure of [(鐣?sup>6-p-cymene)₂Ru₂(娓?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-Methoxyquinoxaline (cas: 6639-82-3Recommanded Product: 6639-82-3).

6-Methoxyquinoxaline (cas: 6639-82-3) 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.Recommanded Product: 6639-82-3

Referemce:
Quinoxaline – Wikipedia,
Quinoxaline | C8H6N2 | ChemSpider

A “Pool and Split” Approach to the Optimization of Challenging Pd-Catalyzed C-N Cross-Coupling Reactions was written by Fordham, James M.;Kollmus, Philipp;Cavegn, Monika;Schneider, Regina;Santagostino, Marco. And the article was included in Journal of Organic Chemistry in 2022.Product Details of 5448-43-1 This article mentions the following:

A screening method for the rapid identification of catalytic conditions for Pd-catalyzed C-N cross-coupling reactions was reported. The strategy evaluates mixtures of precatalysts, ligands and bases to identify productive conditions that are subsequently optimized through two deconvolution steps, which uncover the active catalyst and identify the optimal solvent and base for the catalytic system. The efficacy of this approach was demonstrated through application to a previously reported reaction, whereby both the literature conditions and addnl. solutions were retrieved. The same approach to Ni-catalyzed C-N cross-coupling was investigated in parallel but was found to be less successful due to limited activity of the evaluated reagent combinations. Finally, the utility of this method was showcased by identifying effective conditions for the Pd-catalyzed cross-coupling of complex mols., which not only revealed nonobvious solutions for the processes under evaluation, but also resulted in the discovery of new chem. reactions. 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. 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.Product Details of 5448-43-1

Referemce:
Quinoxaline – Wikipedia,
Quinoxaline | C8H6N2 | ChemSpider

Nickel-catalyzed electrochemical Minisci acylation of aromatic N-heterocycles with α-keto acids via ligand-to-metal electron transfer pathway was written by Ding, Hang;Xu, Kun;Zeng, Cheng-Chu. And the article was included in Journal of Catalysis in 2020.Reference of 6639-82-3 This article mentions the following:

A nickel-catalyzed electrochem. methodol. for the Minisci acylation of aromatic electron-deficient heterocycles with α-keto acids had been developed. The reaction was performed in an undivided cell under constant current conditions, featuring broad scope of substrates and avoiding the conventional utilization of silver-based catalysts in conjunction with excess amount of oxidants. Cyclic voltammetric anal. disclosed that a ligand-to-metal electron transfer process may be involved in the generation of the key acyl radicals. 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 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.Reference of 6639-82-3

Referemce:
Quinoxaline – Wikipedia,
Quinoxaline | C8H6N2 | ChemSpider

Synthesis of quinoxaline- and isoquinolene-5,8-quinones was written by Tsizin, Yu. S.;Chernyak, S. A.. And the article was included in Khimiya Geterotsiklicheskikh Soedinenii in 1975.Formula: C9H8N2O This article mentions the following:

6-Methoxyquinoxaline underwent successive nitration at C-5 and hydrogenation-reduction to give 5-amino-6-methoxyquinoxaline, which was oxidized by Fremy’s salt to give the quinoxaline quinone I. II was prepared similarly. 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

Quadruply Fused Aromatic Heterocycles toward 4 V-Class Robust Organic Cathode-Active Materials was written by Hatakeyama-Sato, Kan;Go, Choitsu;Akahane, Tomoki;Kaseyama, Takahiro;Yoshimoto, Takuji;Oyaizu, Kenichi. And the article was included in Batteries & Supercaps in 2022.SDS of cas: 1910-90-3 This article mentions the following:

Quadruply fused aromatic heterocycles are examined as 4 V-class organic cathode-active materials. A newly synthesized dimethylfluoflavin-substituted polymer displays reversible charge/discharge at high potentials of 3.5 and 4.1 V (vs. Li/Li⁺) as a cathode-active material for organic secondary batteries. The robust redox-active heterocycles enable the long cycle-life (>1000) while maintaining the high potential over 4 V. The linear polymer backbone and radical spin configuration in the heterocycles are the keys to enhancing the voltages and the cycle life. In the experiment, the researchers used many compounds, for example, 6-Bromoquinoxaline-2,3(1H,4H)-dione (cas: 1910-90-3SDS of cas: 1910-90-3).

6-Bromoquinoxaline-2,3(1H,4H)-dione (cas: 1910-90-3) 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.SDS of cas: 1910-90-3

Referemce:
Quinoxaline – Wikipedia,
Quinoxaline | C8H6N2 | ChemSpider

Electrochemical carboxylation of some heteroaromatic compounds was written by Fuchs, Peter;Hess, Ulrich;Holst, Hans Henrik;Lund, Henning. And the article was included in Acta Chemica Scandinavica, Series B: Organic Chemistry and Biochemistry in 1981.Computed Properties of C8H5ClN2 This article mentions the following:

Thirty heteroaromatic compounds (e.g., 4-chloro-2,7,8-trimethylquinoline, 2-chloroquinoxaline, etc.) were investigated by cyclic voltammetry and/or preparative- scale electrolysis (PSE) in the absence and presence of CO₂. The rate constants for dehalogenation of the primarily formed anion radical of halogenated heterocycles were estimated from cyclic-voltammetric data, which indicated that carboxylation without Cl loss is possible under cyclic-voltammetric conditions when the rate constant for cleavage is <∼10⁴ s^-1. PSE confirmed that such halogenated heterocycles may be reductively carboxylated without loss of halogen. In the competition between cleavage and carboxylation, low temperatures favor the latter reaction. In the experiment, the researchers used many compounds, for example, 6-Chloroquinoxaline (cas: 5448-43-1Computed Properties of 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. 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.Computed Properties of C8H5ClN2

Referemce:
Quinoxaline – Wikipedia,
Quinoxaline | C8H6N2 | ChemSpider

Water-involving transfer hydrogenation and dehydrogenation of N-heterocycles over a bifunctional MoNi₄ electrode was written by Li, Mengyang;Liu, Cuibo;Huang, Yi;Han, Shuyan;Zhang, Bin. And the article was included in Chinese Journal of Catalysis in 2021.SDS of cas: 5448-43-1 This article mentions the following:

A room-temperature electrochem. strategy for hydrogenation (deuteration) and reverse dehydrogenation of N-heterocycles over a bifunctional MoNi₄ electrode is developed, which includes the hydrogenation of quinoxaline using H₂O as the hydrogen source with 80% Faradaic efficiency and the reverse dehydrogenation of hydrogen-rich 1,2,3,4-tetrahydroquinoxaline with up to 99% yield and selectivity. The in situ generated active hydrogen atom (H*) is plausibly involved in the hydrogenation of quinoxaline, where a consecutive hydrogen radical coupled electron transfer pathway is proposed. Notably, the MoNi₄ alloy exhibits efficient quinoxaline hydrogenation at an overpotential of only 50 mV, owing to its superior water dissociation ability to provide H* in alk. media. In situ Raman tests indicate that the Ni^II/Ni^III redox couple can promote the dehydrogenation process, representing a promising anodic alternative to low-value oxygen evolution. Impressively, electrocatalytic deuteration is easily achieved with up to 99% deuteration ratios using D₂O. This method is capable of producing a series of functionalized hydrogenated and deuterated quinoxalines. 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. Condensed heterocycles of quinoxalines have become attractive targets in synthetic and medicinal chemistry due to their significant biological activities. 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

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