Heterocyclic Building Blocks-quinoxaline

A Direct Method for Oxidizing Quinoxaline, Tetraazaphenanthrene, and Hexaazatriphenylene Moieties Using Hypervalent λ³-Iodinane Compounds was written by Troian-Gautier, Ludovic;De Winter, Julien;Gerbaux, Pascal;Moucheron, Cecile. And the article was included in Journal of Organic Chemistry in 2013.Safety of 6-Bromoquinoxaline-2,3(1H,4H)-dione This article mentions the following:

An efficient oxidation reaction of various electron-poor quinoxaline-core-containing compounds, such as quinoxalines, 1,4,5,8-tetraazaphenanthrenes, and 1,4,5,8,9,12-hexaazatriphenylene, using [bis(trifluoroacetoxy)iodo]benzene is reported. These compounds are converted into the corresponding quinoxalinediones in good to high yields at room temperature using an acetonitrile/water solvent mixture This unprecedented reaction should enable the synthesis of a wide variety of compounds useful in several fields of chem. In the experiment, the researchers used many compounds, for example, 6-Bromoquinoxaline-2,3(1H,4H)-dione (cas: 1910-90-3Safety of 6-Bromoquinoxaline-2,3(1H,4H)-dione).

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

Referemce:
Quinoxaline – Wikipedia,
Quinoxaline | C8H6N2 | ChemSpider

Binding Mode of an α-Amino Acid-Linked Quinoxaline-2,3-dione Analogue at Glutamate Receptor Subtype GluK1 was written by Demmer, Charles S.;Moeller, Charlotte;Brown, Patricia M. G. E.;Han, Liwei;Pickering, Darryl S.;Nielsen, Birgitte;Bowie, Derek;Frydenvang, Karla;Kastrup, Jette S.;Bunch, Lennart. And the article was included in ACS Chemical Neuroscience in 2015.Application In Synthesis of 6-Bromoquinoxaline-2,3(1H,4H)-dione This article mentions the following:

Two α-amino acid-functionalized quinoxalines, 1a (CNG-10301) and 1b (CNG-10300), of a quinoxaline moiety coupled to an amino acid moiety were designed, synthesized, and characterized pharmacol. While 1a displayed low affinity at native AMPA, KA, and NMDA receptors, and at homomeric GluK1,3 receptors, the affinity for GluK2 was in the midmicromolar range (K_i = 136 μM), 1b displayed low to midmicromolar range binding affinity at all the iGluRs (K_i = 9-126 μM). In functional experiments (outside-out patches excised from transfected HEK293T cells), 100 μM 1a partially blocked GluK1 (33% peak response), while GluK2 was unaffected (96% peak response). Furthermore, 1a was shown not to be an agonist at GluK1 and GluK2 at 100 μM. On the other hand, 100 μM 1b fully antagonized GluK1 (8% peak response) but only partially blocked GluK2 (33% peak response). An X-ray structure at 2.3 Å resolution of 1b in the GluK1-LBD (ligand-binding domain) disclosed an unexpected binding mode compared to the predictions made during the design phase; the quinoxaline moiety remains to act as an amino acid bioisostere, but the amino acid moiety is oriented into a new area within the GluK1 receptor. The structure of the GluK1-LBD with 1b showed a large variation in domain openings of the three mols. from 25° to 49°, demonstrating that the GluK1-LBD is capable of undergoing major domain movements. In the experiment, the researchers used many compounds, for example, 6-Bromoquinoxaline-2,3(1H,4H)-dione (cas: 1910-90-3Application In Synthesis of 6-Bromoquinoxaline-2,3(1H,4H)-dione).

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

Referemce:
Quinoxaline – Wikipedia,
Quinoxaline | C8H6N2 | ChemSpider

Homogeneous Nickel-Catalyzed Sustainable Synthesis of Quinoline and Quinoxaline under Aerobic Conditions was written by Bains, Amreen K.;Singh, Vikramjeet;Adhikari, Debashis. And the article was included in Journal of Organic Chemistry in 2020.Related Products of 5448-43-1 This article mentions the following:

Dehydrogenative coupling-based reactions have emerged as an efficient route toward the synthesis of a plethora of heterocyclic rings. Herein, we report an efficacious, nickel-catalyzed synthesis of two important heterocycles such as quinoline and quinoxaline. The catalyst is molecularly defined, is phosphine-free, and can operate at a mild reaction temperature of 80°C. Both the heterocycles can be easily assembled via double dehydrogenative coupling, starting from 2-aminobenzyl alc./1-phenylethanol and diamine/diol, resp., in a shorter span of reaction time. This environmentally benign synthetic protocol employing an inexpensive catalyst can rival many other transition-metal systems that have been developed for the fabrication of two putative heterocycles. Mechanistically, the dehydrogenation of secondary alc. follows clean pseudo-first-order kinetics and exhibits a sizable kinetic isotope effect. Intriguingly, this catalyst provides an example of storing the trapped hydrogen in the ligand backbone, avoiding metal-hydride formation. Easy regeneration of the oxidized form of the catalyst under aerobic/O₂ oxidation makes this protocol eco-friendly and easy to handle. In the experiment, the researchers used many compounds, for example, 6-Chloroquinoxaline (cas: 5448-43-1Related Products 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. The antitumoral properties of quinoxaline compounds have been of interest. Recently, quinoxaline and its analogs have been investigated as the catalyst’s ligands.Related Products of 5448-43-1

Referemce:
Quinoxaline – Wikipedia,
Quinoxaline | C8H6N2 | ChemSpider

The infrared spectra of polycyclic heteroaromatic compounds. III. 2-, 5-, and 6-substituted quinoxalines was written by Cheeseman, G. W. H.;Katritzky, A. R.;Ridgewell, B. J.. And the article was included in Journal of the Chemical Society in 1963.Name: 6-Methoxyquinoxaline This article mentions the following:

The infrared spectra of quinoxaline, 9 of its 2-substituted, 5 of its 5-substituted, and 8 of its 6-substituted derivatives are recorded and discussed, with tentative assignments of characteristic bands to specific mol. vibration modes. Cf. CA 56, 1073g. In the experiment, the researchers used many compounds, for example, 6-Methoxyquinoxaline (cas: 6639-82-3Name: 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-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: 6-Methoxyquinoxaline

Referemce:
Quinoxaline – Wikipedia,
Quinoxaline | C8H6N2 | ChemSpider

3-Arylamino-quinoxaline-2-carboxamides inhibit the PI3K/Akt/mTOR signaling pathways to activate P53 and induce apoptosis was written by Chen, Nan-Ying;Lu, Ke;Yuan, Jing-Mei;Li, Xiao-Juan;Gu, Zi-Yu;Pan, Cheng-Xue;Mo, Dong-Liang;Su, Gui-Fa. And the article was included in Bioorganic Chemistry in 2021.Synthetic Route of C11H9ClN2O2 This article mentions the following:

Thirty-eight new 3-arylaminoquinoxaline-2-carboxamide derivatives were in silico designed, synthesized and their cytotoxicity against five human cancer cell lines and one normal cells WI-38 were evaluated. Mol. mechanism studies indicated that N-(3-Aminopropyl)-3-(4-chlorophenyl) amino-quinoxaline-2-carboxamide (6be), the compound with the most potent anti-proliferation can inhibit the PI3K-Akt-mTOR pathway via down regulating the levels of PI3K, Akt, p-Akt, p-mTOR and simultaneously inhibit the phosphorylation of Thr308 and Ser473 residues in Akt kinase to servers as a dual inhibitor. Further investigation revealed that 6be activate the P53 signal pathway, modulated the downstream target gene of Akt kinase such p21, p27, Bax and Bcl-2, caused the fluctuation of intracellular ROS, Ca2+ and mitochondrial membrane potential to induce cell cycle arrest and apoptosis in MGC-803 cells. 6be also display moderate anti-tumor activity in vivo while displaying no obvious adverse signs during the drug administration. The results suggest that 3-arylaminoquinoxaline-2-carboxamide derivatives might server as new scaffold for development of PI3K-Akt-mTOR inhibitor. In the experiment, the researchers used many compounds, for example, Ethyl 3-chloroquinoxaline-2-carboxylate (cas: 49679-45-0Synthetic Route of C11H9ClN2O2).

Ethyl 3-chloroquinoxaline-2-carboxylate (cas: 49679-45-0) 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 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.Synthetic Route of C11H9ClN2O2

Referemce:
Quinoxaline – Wikipedia,
Quinoxaline | C8H6N2 | ChemSpider

The infrared spectra of polycyclic heteroaromatic compounds. III. 2-, 5-, and 6-substituted quinoxalines was written by Cheeseman, G. W. H.;Katritzky, A. R.;Ridgewell, B. J.. And the article was included in Journal of the Chemical Society in 1963.Formula: C8H5ClN2 This article mentions the following:

The infrared spectra of quinoxaline, 9 of its 2-substituted, 5 of its 5-substituted, and 8 of its 6-substituted derivatives are recorded and discussed, with tentative assignments of characteristic bands to specific mol. vibration modes. Cf. CA 56, 1073g. 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. 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.Formula: C8H5ClN2

Referemce:
Quinoxaline – Wikipedia,
Quinoxaline | C8H6N2 | ChemSpider

Iron-catalyzed Minisci acylation of N-heteroarenes with α-keto acids was written by Wang, Xiu-Zhi;Zeng, Cheng-Chu. And the article was included in Tetrahedron in 2019.Product Details of 6639-82-3 This article mentions the following:

An efficient and mild protocol was developed for the Minisci acylation reactions of nitrogen-containing heteroarenes with α-keto acids to afford acyl-pyrazine derivatives e.g., I. Distinct from the conventional Minisci acylation conditions, the chem. was performed using non-noble metal Fe(II), instead of expensive Ag(I) salt as catalyst. A wide range of substrates, including aliphatic or aromatic α-keto acids, as well as various N-heteroarenes, proved to be compatible with the protocol. 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 in the treatment of bacterial, cancer, and HIV infections. Moreover, varenicline, a clinical drug is used for treating nicotine addiction, also contains quinoxaline moiety.Product Details of 6639-82-3

Referemce:
Quinoxaline – Wikipedia,
Quinoxaline | C8H6N2 | ChemSpider

Copper-Catalyzed Hydroxylation of (Hetero)aryl Halides under Mild Conditions was written by Xia, Shanghua;Gan, Lu;Wang, Kailiang;Li, Zheng;Ma, Dawei. And the article was included in Journal of the American Chemical Society in 2016.Name: 6-Chloroquinoxaline This article mentions the following:

In the presence of Cu(acac)₂ and N,N’-bis(4-hydroxyl-2,6-dimethylphenyl)oxalamide, aryl and heteroaryl chlorides, bromides, and iodides underwent hydroxylation reactions in DMSO/H₂O to yield phenols and aryl and heteroaryl alcs. A wide range of aryl and heteroaryl chlorides bearing either electron-donating or electron-withdrawing groups underwent hydroxylation at 130 °C to provide the corresponding phenols and hydroxylated heteroarenes in 52-96% yields. When more reactive aryl and heteroaryl bromides and iodides were employed, the hydroxylation reactions could be performed at 80° and 60°, resp., using 0.5 mol% of Cu(acac)₂. 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. 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.Name: 6-Chloroquinoxaline

Referemce:
Quinoxaline – Wikipedia,
Quinoxaline | C8H6N2 | ChemSpider

Mild and General Palladium-Catalyzed Synthesis of Methyl Aryl Ethers Enabled by the Use of a Palladacycle Precatalyst was written by Cheung, Chi Wai;Buchwald, Stephen L.. And the article was included in Organic Letters in 2013.Recommanded Product: 6639-82-3 This article mentions the following:

A general method for the Pd-catalyzed coupling of methanol with (hetero)aryl halides is described. The reactions proceed under mild conditions with a wide range of aryl and heteroaryl halides to give Me aryl ethers in high yield. E.g., in presence of palladacycle precatalyst I (L = tBuBrettPhos) and the ligand tBuBrettPhos, arylation of MeOH by 4-Me₃CC₆H₄Cl gave 93% 4-Me₃CC₆H₄OMe. 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. 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.Recommanded Product: 6639-82-3

Referemce:
Quinoxaline – Wikipedia,
Quinoxaline | C8H6N2 | ChemSpider

Rapid and Convenient Synthesis of Original 5-Substituted Quinolino[3,4-b]quinoxalin-6(5H)-ones under Eco-Friendly Conditions was written by Khoumeri, Omar;Vanelle, Francois-Xavier;Crozet, Maxime D.;Terme, Thierry;Vanelle, Patrice. And the article was included in Synlett in 2016.Formula: C11H9ClN2O2 This article mentions the following:

The synthesis of 5-(substituted)quinolino[3,4-b]quinoxalin-6(5H)-one derivatives I [R = H, 2-Cl, 4-Me, etc.] from Et 3-(2-bromophenyl)quinoxaline-2-carboxylate under one-pot Buchwald-Hartwig coupling-lactamization reaction was reported. In the experiment, the researchers used many compounds, for example, Ethyl 3-chloroquinoxaline-2-carboxylate (cas: 49679-45-0Formula: C11H9ClN2O2).

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. 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.Formula: C11H9ClN2O2

Referemce:
Quinoxaline – Wikipedia,
Quinoxaline | C8H6N2 | ChemSpider