Month: January 2023

Efficient Microwave-Assisted Pd-Catalyzed Hydroxylation of Aryl Chlorides in the Presence of Carbonate was written by Yu, Chao-Wu;Chen, Grace S.;Huang, Chen-Wei;Chern, Ji-Wang. And the article was included in Organic Letters in 2012.Related Products of 5448-43-1 This article mentions the following:

An efficient microwave-assisted, palladium-catalyzed hydroxylation of aryl chlorides in the presence of a weak base carbonate was developed, which rapidly converts aryl and heteroaryl chlorides to phenols, and can be used when the aryl chloride is functionalized with a ketone, aldehyde, ester, nitrile, or amide. 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. 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. 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

B(C₆F₅)₃-promoted hydrogenations of N-heterocycles with ammonia borane was written by Ding, Fangwei;Zhang, Yiliang;Zhao, Rong;Jiang, Yanqiu;Bao, Robert Li-Yuan;Lin, Kaifeng;Shi, Lei. And the article was included in Chemical Communications (Cambridge, United Kingdom) in 2017.Electric Literature of C8H5ClN2 This article mentions the following:

A transition-metal-free method for the B(C₆F₅)₃-promoted hydrogenations of N-heterocycles using ammonia borane under mild reaction conditions was developed. The reaction afforded a broad range of hydrogenated products in moderate to good yields. The enantioselective versions for the corresponding products were also investigated via our approach, showing good feasibility. In the experiment, the researchers used many compounds, for example, 6-Chloroquinoxaline (cas: 5448-43-1Electric Literature 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. 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.Electric Literature of C8H5ClN2

Referemce:
Quinoxaline – Wikipedia,
Quinoxaline | C8H6N2 | ChemSpider

Synthesis and some reactions of quinoxalinecarboazides was written by Moustafa, O. S.. And the article was included in Journal of the Chinese Chemical Society (Taipei) in 2000.Computed Properties of C11H9ClN2O2 This article mentions the following:

Chlorination of Et (quinoxalin-2(1H)one)-3-carboxylate (I) gave Et (2-chloroquinoxaline)-3-carboxylate (II). Thionation of I by P₂S₅ or II by thiourea yielded the same thione product. Reaction of chloro compound II or the thio compound with hydrazine hydrate gave pyrazolylquinoxaline. The reaction of ester I with thiourea or hydrazine hydrate afforded a pyrimidoquinoxaline or carbohydrazide. The reaction of the carbohydrazide with carbon disulfide in basic medium followed by alkylation afforded oxadiazoloquinoxaline derivatives Carboazide III was produced by reaction of the pyrimidoquinoxaline with nitrous acid. Compound III on heating in an inert solvent, with or without amines, in alcs. or hydrolysis in H₂O undergoes Curtius rearrangements. Reaction of IV with thiosemicarbazide gave a triazoloquinoxaline which on reaction with alkylhalides or hydrazine hydrate yielded S-alkyl or hydrazino derivatives while hydrolysis of IV gave an 3-aminoquinoxalinone which was used as an intermediate. In the experiment, the researchers used many compounds, for example, Ethyl 3-chloroquinoxaline-2-carboxylate (cas: 49679-45-0Computed Properties of 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. 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.Computed Properties of C11H9ClN2O2

Referemce:
Quinoxaline – Wikipedia,
Quinoxaline | C8H6N2 | ChemSpider

The synthesis of novel, visible-wavelength, oxidizable polymerization sensitizers based on the 8-halogeno-5,12-dihydroquinoxalino[2,3-b]quinoxaline skeleton was written by Podsiadly, Radoslaw;Szymczak, Agnieszka M.;Podemska, Karolina. And the article was included in Dyes and Pigments in 2009.Quality Control of 6-Bromoquinoxaline-2,3(1H,4H)-dione This article mentions the following:

Novel dyes, based on the 8-halogeno-5,12-dihydroquinoxalino[2,3-b]quinoxaline skeleton, were synthesized and characterized using ¹H NMR spectroscopy and chem. ionization mass spectroscopy. Their electrochem. and spectral properties, such as absorption and emission spectra, quantum yield of fluorescence and quantum yield of singlet oxygen generation, were also measured. These dyes were used as oxidizable sensitizers for diphenyliodonium and N-alkoxypyridinium salts. Photoredox pairs, consisting of dyes and pyridinium or iodonium salts, were found to be effective visible-wavelength initiators of free radical or cationic polymerization, resp. The ability of each dye to act as a photoinitiator strongly depended upon its chem. structure. The heavy atoms present in the chem. structure could lead to excited triplet states within the dye, thereby facilitating electron transfer from these states. In the experiment, the researchers used many compounds, for example, 6-Bromoquinoxaline-2,3(1H,4H)-dione (cas: 1910-90-3Quality Control of 6-Bromoquinoxaline-2,3(1H,4H)-dione).

6-Bromoquinoxaline-2,3(1H,4H)-dione (cas: 1910-90-3) 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 in the treatment of bacterial, cancer, and HIV infections. Moreover, varenicline, a clinical drug is used for treating nicotine addiction, also contains quinoxaline moiety.Quality Control of 6-Bromoquinoxaline-2,3(1H,4H)-dione

Referemce:
Quinoxaline – Wikipedia,
Quinoxaline | C8H6N2 | ChemSpider

Ruthenium(II)-Catalyzed Regioselective 1,2-Hydrosilylation of N-Heteroarenes and Tetrel Bonding Mechanism was written by Behera, Deepak;Thiyagarajan, Subramanian;Anjalikrishna, Puthannur K.;Suresh, Cherumuttathu H.;Gunanathan, Chidambaram. And the article was included in ACS Catalysis in 2021.Category: quinoxaline This article mentions the following:

An efficient regioselective dearomatization of N-heteroarenes using a ruthenium precatalyst [Ru-(p-cymene)(PCy₃)Cl₂] 1 is achieved. Reactions were performed under mild and neat conditions. A wide variety of N-heteroarenes undergo the addition of silanes in the presence of precatalyst 1, leading to exclusive N-silyl-1,2-dihydroheteroarene products. This catalytic method displays a broad substrate scope; quinolines, isoquinolines, benzimidazoles, quinoxalines, pyrazines, pyrimidines, and pyridines undergo highly selective 1,2-dearomatization. Both electron-donating and electron-withdrawing substituents on N-heteroaromatics are well tolerated in this protocol. Mechanistic studies indicate the presence of [Ru-(p-cymene) (PCy₃)HCl] 4 in the reaction mixture, which may be the resting state of the catalyst. The complete catalytic cycle as revealed from d. functional theory (DFT) studies show that the product formation is governed by N → Si tetrel bonding. Initially, PCy₃ dissociates from 1, and further reaction of [(p-cymene)RuCl₂] 20 with silane generates the catalytically active intermediate [(p-cymene)RuHCl] 7. Heteroarene coordinates with 7, and subsequent dearomative 1,3-hydride transfer to the C2 position of the heteroaryl ligand generates an amide-ligated intermediate in which the reaction of silane occurs through a tetrel bonding and provides a selective pathway for 1,2-addition DFT studies also revealed that ruthenium-catalyzed 1,4-hydroboration of pyridines is a facile process with a free energy barrier of 3.2 kcal/mol, whereas a pathway for the 1,2-hydroboration product is not observed due to the steric effects exerted by Me groups on pinacolborane (HBpin) and p-cymene. Notably, enabled by the amine-amide inter-conversion of the coordinated heteroarene ligand, the +2 oxidation state of ruthenium intermediates remains unchanged throughout the catalytic cycle. 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 derivatives are important constituents of pharmacologically active compounds, including antibacterial, antibiotic and antineoplastic, antifungal, anti-inflammatory and analgesic drugs. 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

Discovery of potent pteridine reductase inhibitors to guide antiparasite drug development was written by Cavazzuti, Antonio;Paglietti, Giuseppe;Hunter, William N.;Gamarro, Francisco;Piras, Sandra;Loriga, Mario;Alleca, Sergio;Corona, Paola;McLuskey, Karen;Tulloch, Lindsay;Gibellini, Federica;Ferrari, Stefania;Costi, Maria Paola. And the article was included in Proceedings of the National Academy of Sciences of the United States of America in 2008.Safety of Ethyl 3-chloroquinoxaline-2-carboxylate This article mentions the following:

Pteridine reductase (PTR1) is essential for salvage of pterins by parasitic trypanosomatids and is a target for the development of improved therapies. To identify inhibitors of Leishmania major and Trypanosoma cruzi PTR1, a rapid-screening strategy using a folate-based library was combined with structure-based design. Assays were carried out against folate-dependent enzymes including PTR1, dihydrofolate reductase (DHFR), and thymidylate synthase. Affinity profiling determined selectivity and specificity of a series of quinoxaline and 2,4-diaminopteridine derivatives, and nine compounds showed greater activity against parasite enzymes compared with human enzymes. Compound I [R = H, Me (II)] displayed a K_i of 100 nM toward LmPTR1, and the crystal structure of the LmPTR1:NADPH:I ternary complex revealed a substrate-like binding mode distinct from that previously observed for similar compounds A second round of design, synthesis, and assay produced a compound II with a significantly improved K_i (37 nM) against LmPTR1, and the structure of this complex was also determined Biol. evaluation of selected inhibitors was performed against the extracellular forms of T. cruzi and L. major, both wild-type and overexpressing PTR1 lines, as a model for PTR1-driven antifolate drug resistance and the intracellular form of T. cruzi. An additive profile was observed when PTR1 inhibitors were used in combination with known DHFR inhibitors, and a reduction in toxicity of treatment was observed with respect to administration of a DHFR inhibitor alone. The successful combination of antifolates targeting two enzymes indicates high potential for such an approach in the development of previously undescribed antiparasitic drugs. In the experiment, the researchers used many compounds, for example, Ethyl 3-chloroquinoxaline-2-carboxylate (cas: 49679-45-0Safety of Ethyl 3-chloroquinoxaline-2-carboxylate).

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.Safety of Ethyl 3-chloroquinoxaline-2-carboxylate

Referemce:
Quinoxaline – Wikipedia,
Quinoxaline | C8H6N2 | ChemSpider

Electrochemical reactions. XV. Factors which determine the rate of carbon-halogen bond fragmentation in radical anions illustrated by halogenated derivatives of quinoline, quinoxaline, and phenazine was written by Alwair, Khaled;Grimshaw, James. And the article was included in Journal of the Chemical Society, Perkin Transactions 2: Physical Organic Chemistry (1972-1999) in 1973.Electric Literature of C8H5ClN2 This article mentions the following:

Halo derivatives of quinoline, quinoxaline, and phenazine in the potential region of the 1st reduction waves were examined by polarog. and cyclic voltammetry in DMF at an Hg cathode. The stability of the C-halogen bond in a halogenated radical anion depended on bond strength and the redox potential of the substrate-radical anion couple. In the experiment, the researchers used many compounds, for example, 6-Chloroquinoxaline (cas: 5448-43-1Electric Literature of C8H5ClN2).

6-Chloroquinoxaline (cas: 5448-43-1) 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.Electric Literature of C8H5ClN2

Referemce:
Quinoxaline – Wikipedia,
Quinoxaline | C8H6N2 | ChemSpider

One-pot synthesis of substituted bistetrazolo[1,5-a:5′,1′-c]quinoxalines was written by Srinivas, B.;Prasanna, B.;Ravinder, M.. And the article was included in Chemical Science Transactions in 2013.Safety of 6-Bromoquinoxaline-2,3(1H,4H)-dione This article mentions the following:

A novel methodol. was developed for synthesis of substituted bis tetrazolo[1,5-a;5′,1′-c]quinoxalines via one pot three-component condensation of quinoxaline-2,3-diones, phosphorous oxychloride and sodium azide. The ambient conditions, excellent product yields, easy work up procedures and short reaction time make this synthetic strategy a better protocol for the synthesis of newer bistetrazoloquinoxalines. The structures of all these compounds were confirmed by their IR, ¹H NMR, ¹³C NMR and mass spectral anal. 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. 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.Safety of 6-Bromoquinoxaline-2,3(1H,4H)-dione

Referemce:
Quinoxaline – Wikipedia,
Quinoxaline | C8H6N2 | ChemSpider

Proton magnetic resonance spectra in aromatic systems. XIII. Heteroaromatic series. 5. 6-Substituted quinoxalines was written by Sasaki, Yoshio;Hatanaka, Minoru;Suzuki, Miyoko. And the article was included in Yakugaku Zasshi in 1969.Category: quinoxaline This article mentions the following:

The chem. shifts of the ring 1H of 6-quinoxalines have been corrected for N anisotropy, N elec. field, and ring current effects. The corrected shifts have also been correlated with the substituent constants σπ, and those corresponding to the π-electron charge density-ρ-distributions were estimated, and converted to ρ values. In the experiment, the researchers used many compounds, for example, 6-Methoxyquinoxaline (cas: 6639-82-3Category: quinoxaline).

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.Category: quinoxaline

Referemce:
Quinoxaline – Wikipedia,
Quinoxaline | C8H6N2 | ChemSpider

Organic Base Enabled Nickel-Catalyzed Mono-α-Arylation of Feedstock Solvents was written by MacMillan, Joshua W. M.;McGuire, Ryan T.;Stradiotto, Mark. And the article was included in Chemistry – A European Journal in 2022.Application of 5448-43-1 This article mentions the following:

Authors report on authors’ successful development of the first metal-catalyzed mono-α-arylation of carbonyl compounds employing a soluble organic base. The scope of these Ni/DalPhos-catalyzed transformations encompasses a range of (hetero)aryl halides (Cl, Br, I) and phenol-derived electrophiles (sulfonates, carbonates, carbamates, sulfamates), including active pharmaceutical ingredients (chloroquine, clozapine), in combination with the typically problematic feedstock small mol. substrates acetone, dimethylacetamide, and for the first time with any metal catalyst/base, Et acetate. In the experiment, the researchers used many compounds, for example, 6-Chloroquinoxaline (cas: 5448-43-1Application of 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.Application of 5448-43-1

Referemce:
Quinoxaline – Wikipedia,
Quinoxaline | C8H6N2 | ChemSpider