Day: January 4, 2023

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

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

Referemce:
Quinoxaline – Wikipedia,
Quinoxaline | C8H6N2 | ChemSpider

Palladium-Catalyzed Amination of Aryl Chlorides and Bromides with Ammonium Salts was written by Green, Rebecca A.;Hartwig, John F.. And the article was included in Organic Letters in 2014.Reference of 5448-43-1 This article mentions the following:

We report the palladium-catalyzed coupling of aryl halides with ammonia and gaseous amines as their ammonium salts. The coupling of aryl chlorides and ortho-substituted aryl bromides with ammonium sulfate forms anilines with higher selectivity for the primary arylamine over the diarylamine than couplings with ammonia in dioxane. The resting state for the reactions of aryl chlorides is different from the resting state for the reactions of aryl bromides, and this change in resting states is proposed to account for a difference in selectivities for reactions of the two haloarenes. 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. 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 5448-43-1

Referemce:
Quinoxaline – Wikipedia,
Quinoxaline | C8H6N2 | ChemSpider

Aqueous Hydrofluoric Acid Catalyzed Facile Synthesis of 2,3,6-Substituted Quinoxalines was written by Chandra Shekhar, A.;Ravi Kumar, A.;Sathaiah, G.;Raju, K.;Srinivas, P. V. S. S.;Shanthan Rao, P.;Narsaiah, B.. And the article was included in Journal of Heterocyclic Chemistry in 2014.Safety of 6-Chloroquinoxaline This article mentions the following:

A versatile synthetic route for the preparation of 2,3,6-trisubstituted quinoxalines I (R = H, NO₂, Cl, COPh, R¹ = H, Me, Ph, 4-FC₆H₄, 4-F₃CC₆H₄) in excellent yield is developed from o-diamines and 1,2-dicarbonyl compounds in which aqueous hydrofluoric acid was employed as the medium and catalyst. Other salient features of this protocol include milder conditions, absence of coupling agents, and easy workup procedures. In the experiment, the researchers used many compounds, for example, 6-Chloroquinoxaline (cas: 5448-43-1Safety of 6-Chloroquinoxaline).

6-Chloroquinoxaline (cas: 5448-43-1) 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.Safety of 6-Chloroquinoxaline

Referemce:
Quinoxaline – Wikipedia,
Quinoxaline | C8H6N2 | ChemSpider

Development and Synthesis of DNA-Encoded Benzimidazole Library was written by Ding, Yun;Chai, Jing;Centrella, Paolo A.;Gondo, Chenaimwoyo;De Lorey, Jennifer L.;Clark, Matthew A.. And the article was included in ACS Combinatorial Science in 2018.Quality Control of Quinoxaline-5-carbaldehyde This article mentions the following:

Encoded library technol. (ELT) is an effective approach to the discovery of novel small-mol. ligands for biol. targets. A key factor for the success of the technol. is the chem. diversity of the libraries. Here we report the development of DNA-conjugated benzimidazoles. Using 4-fluoro-3-nitrobenzoic acid as a key synthon, we synthesized a 320 million-member DNA-encoded benzimidazole library using Fmoc-protected amino acids, amines and aldehydes as diversity elements. Affinity selection of the library led to the discovery of a novel, potent and specific antagonist of the NK3 receptor. In the experiment, the researchers used many compounds, for example, Quinoxaline-5-carbaldehyde (cas: 141234-08-4Quality Control of Quinoxaline-5-carbaldehyde).

Quinoxaline-5-carbaldehyde (cas: 141234-08-4) 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.Quality Control of Quinoxaline-5-carbaldehyde

Referemce:
Quinoxaline – Wikipedia,
Quinoxaline | C8H6N2 | ChemSpider

Nickel/Photoredox-Catalyzed Methylation of (Hetero)aryl Chlorides Using Trimethyl Orthoformate as a Methyl Radical Source was written by Kariofillis, Stavros K.;Shields, Benjamin J.;Tekle-Smith, Makeda A.;Zacuto, Michael J.;Doyle, Abigail G.. And the article was included in Journal of the American Chemical Society in 2020.Name: 6-Chloroquinoxaline This article mentions the following:

A radical approach for the methylation of (hetero)aryl chlorides R-Cl (R = 4-CNC₆H₄, 2-CF₃C₆H₄, 9-oxo-thioxanthen-2-yl, 4-(6-methylpyridin-2-yl)phenyl, 4-phenythiazol-2-yl, etc.) using nickel/photoredox catalysis wherein tri-Me orthoformate, a common laboratory solvent, serves as a Me source has been described. This method permits methylation of (hetero)aryl chlorides and acyl chlorides R¹C(O)Cl (R¹ = (CH₂)₁₀-CH₃, adamantan-1-yl, C₆H₅O, N,N-diphenylamino, etc.) at an early and late stage with broad functional group compatibility. Mechanistic investigations indicate that tri-Me orthoformate serves as a source of Me radical via β-scission from a tertiary radical generated upon chlorine-mediated hydrogen atom transfer. 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. 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. 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-Chloroquinoxaline

Referemce:
Quinoxaline – Wikipedia,
Quinoxaline | C8H6N2 | ChemSpider

Nickel-Catalyzed Amination of Aryl Chlorides with Ammonia or Ammonium Salts was written by Green, Rebecca A.;Hartwig, John F.. And the article was included in Angewandte Chemie, International Edition in 2015.Reference of 5448-43-1 This article mentions the following:

The nickel-catalyzed amination of aryl chlorides to form primary arylamines with ammonia or ammonium sulfate and a well-defined single-component nickel(0) pre-catalyst, containing a Josiphos ligand and an η²-bound benzonitrile ligand, was reported. This system also catalyzed the coupling of aryl chlorides with gaseous amines in the form of their hydrochloride salts. 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. 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 5448-43-1

Referemce:
Quinoxaline – Wikipedia,
Quinoxaline | C8H6N2 | ChemSpider

Design and synthesis of a novel mitochondria-targeted osteosarcoma theranostic agent based on a PIM1 kinase inhibitor was written by Yi, Xinzeyu;Cao, Zhi;Yuan, Ying;Li, Wen;Cui, Xinyue;Chen, Zilin;Hu, Xiang;Yu, Aixi. And the article was included in Journal of Controlled Release in 2021.Formula: C11H9ClN2O2 This article mentions the following:

Osteosarcoma (OS) is the most common malignancy of the skeletal system, with a poor prognosis and high rate of recurrence. Adequate surgical margin and adjuvant chemotherapy improve the overall survival and limb salvage rate of osteosarcoma patients. Previous studies have showed that OS exhibits an increase in the expression of proviral integration site for Moloney murine leukemia virus 1 (PIM1) kinase, and high levels of PIM1 are also associated with poor OS prognosis and metastasis. We exploited the overexpression of proto-oncogenic PIM1 in OS toward the development of a novel near-IR imaging and targeted therapeutic agent, namely QCAi-Cy7d by conjugating a PIM1 small mol. inhibitor and heptamethine cyanine dye, for simultaneous guiding surgery and chemotherapy. QCAi-Cy7d showed targeted imaging and anticancer activities against OS in vitro and vivo without any obvious toxicity, and its antitumoral activity was much greater than the parent PIMI inhibitor. These results demonstrated the potential of new conjugate of PIM1 inhibitor and near-IR imaging, supporting structure-based design and development of theranostic agents for precise tumor imaging and targeted treatment. 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. 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. Modifying quinoxaline structure it is possible to obtain a wide variety of biomedical applications, namely antimicrobial activities and chronic and metabolic diseases treatment.Formula: C11H9ClN2O2

Referemce:
Quinoxaline – Wikipedia,
Quinoxaline | C8H6N2 | ChemSpider

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