Category: quinoxaline

Rapid, efficient and eco-friendly procedure for the synthesis of quinoxalines under solvent-free conditions using sulfated polyborate as a recyclable catalyst was written by Indalkar, Krishna S.;Khatri, Chetan K.;Chaturbhuj, Ganesh U.. And the article was included in Journal of Chemical Sciences (Berlin, Germany) in 2017.Name: 6-Chloroquinoxaline This article mentions the following:

An efficient and inexpensive sulfated polyborate catalyst was applied for the rapid synthesis of quinoxaline derivatives from various substituted o-phenylenediamines and 1,2-diketones/α-hydroxy ketones using sulfated polyborate. The catalyst had the advantage of Lewis as well as Bronsted acidity and recyclability without significant loss in catalytic activity. The key advantages of the present method were high yields, short reaction times, solvent-free condition, easy workup, and ability to tolerate a variety of functional groups, which gave economical as well as ecol. rewards. 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. 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.Name: 6-Chloroquinoxaline

Referemce:
Quinoxaline – Wikipedia,
Quinoxaline | C8H6N2 | ChemSpider

Nickel-Catalyzed N-Arylation of Amides with (Hetero)aryl Electrophiles by Using a DBU/NaTFA Dual-Base System was written by Lundrigan, Travis;Tassone, Joseph P.;Stradiotto, Mark. And the article was included in Synlett in 2021.Recommanded Product: 5448-43-1 This article mentions the following:

The first nickel-catalyzed N-arylation of amides with (hetero)aryl (pseudo)halides employing an organic amine base is described. By using a bis(cyclooctadienyl)nickel/8-[2-(dicyclohexylphosphinyl)phenyl]-1,3,5,7-tetramethyl-2,4,6-trioxa-8-phosphaadamantane catalyst mixture in combination with DBU/NaTFA as a dual-base system, a diversity of (hetero)aryl chloride, bromide, tosylate, and mesylate electrophiles were successfully cross-coupled with structurally diverse primary amides, as well as a selection of secondary amide, lactam, and oxazolidone nucleophiles. 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 is isomeric with other naphthyridines including quinazoline, phthalazine and cinnoline. 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

Discovery of new anti-depressants from structurally novel 5-HT₃ receptor antagonists: Design, synthesis and pharmacological evaluation of 3-ethoxyquinoxalin-2-carboxamides was written by Mahesh, Radhakrishnan;Devadoss, Thangaraj;Pandey, Dilip Kumar;Bhatt, Shvetank. And the article was included in Bioorganic & Medicinal Chemistry Letters in 2011.Reference of 49679-45-0 This article mentions the following:

A novel series of 3-ethoxyquinoxalin-2-carboxamides were designed as per the pharmacophoric requirements of 5-HT₃ receptor antagonist using ligand-based approach. The desired carboxamides were synthesized from the key intermediate, 3-ethoxyquinoxalin-2-carboxylic acid by coupling with appropriate amines in the presence of 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride and 1-hydroxybenzotriazole. The 5-HT₃ receptor antagonism was evaluated in longitudinal muscle myenteric plexus preparation from guinea pig ileum against 5-HT₃ agonist, 2-methyl-5-HT, which was expressed in the form of pA ₂ values. (3-Ethoxyquinoxalin-2-yl)(4-methylpiperazin-1-yl)methanone was found to be the most active compound, which expressed a pA ₂ value of 7.7. In forced swim test, the compounds with higher pA ₂ value exhibited good anti-depressant-like activity and compounds with lower pA ₂ value failed to show activity as compared to the vehicle-treated group. 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. 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 49679-45-0

Referemce:
Quinoxaline – Wikipedia,
Quinoxaline | C8H6N2 | ChemSpider

A comparison of nucleophilic reactions of 3-benzenesulfonyloxyalloxazine and its 1-methyl analog was written by Hamby, James M.;Bauer, Ludwig. And the article was included in Journal of Heterocyclic Chemistry in 1987.Related Products of 49679-45-0 This article mentions the following:

Reactions of 3-benzenesulfonyloxyalloxazines I (R = H, Me) with a number of nucleophilic reagents are reported. Relatively small nucleophiles, such as HO^–, MeOH, EtOH, MeNH₂, N₂H₄, and HONH₂, converted I (R = H) to 4-carboxy-s-triazolo[4,3-a]quinoxalin-1(2H)-ones and the corresponding esters ar amides. As the size of the amine increased from MeNH₂ to EtNH₂, Me₂NH₂, PrNH₂, and Me₂CHNH₂, there were obtained 4-(carboxamido)-s-triazolo[4,3-a]quinoxalin-1(2H)-ones, (1-carboxamido)imidazolo[4,5-b]quinoxalines, and 2,3-bis(ureido)quinoxalines. NaH or KCN in hot DMF degraded I (R = H) to imidazolo[4,5-b]quinoxaline. However, MeSH and PhCH₂SH ions attacked the sulfonate group of I (R = H) to form 3-hydroxyalloxazine. I (R = Me) reacted with MeOH, EtOH, PrOH, and to some degree Me₂CHOH, in the presence of Et₃N to furnish anhydro-1-hydroxy-3-methyl-4-(alkoxycarbonyl)-s-triazolo[4,3-a]quinoxalinium hydroxides. However, NaOMe in MeOH converted I (R = Me) to a mixture of anhydro-1-hydroxy-3-methyl-s-triazolo[4,3-a]quinoxalinium hydroxide (II) and 1-methyl-3-hydroxyflavazole. A saturated aqueous solution of Et₃N transformed I (R = Me) to II, apparently via the corresponding unstable 4-carboxylic acid. Reactions of I (R = Me) with a number of aliphatic amines yielded either amides based on the above mesoionic system or on the 3-carboxamido-2-quinoxalyl semicarbazide structure. Reaction of I (R = Me) with KCN furnished 1-methylimidazolo[4,5-b]quinoxaline. Mechanisms to explain all of the degradations are advanced. In the experiment, the researchers used many compounds, for example, Ethyl 3-chloroquinoxaline-2-carboxylate (cas: 49679-45-0Related Products of 49679-45-0).

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

Referemce:
Quinoxaline – Wikipedia,
Quinoxaline | C8H6N2 | ChemSpider

Nickel-Catalyzed N-Arylation of Primary Amides and Lactams with Activated (Hetero)aryl Electrophiles was written by Lavoie, Christopher M.;MacQueen, Preston M.;Stradiotto, Mark. And the article was included in Chemistry – A European Journal in 2016.Application In Synthesis of 6-Chloroquinoxaline This article mentions the following:

The first nickel-catalyzed N-arylation of amides with (hetero)aryl (pseudo)halides was reported, enabled by use of the air-stable pre-catalyst (PAd-DalPhos)Ni(o-tolyl)Cl. A range of structurally diverse primary amides and lactams were cross-coupled successfully with activated (hetero)aryl chloride, bromide, triflate, tosylate, mesylate, and sulfamate electrophiles. In the experiment, the researchers used many compounds, for example, 6-Chloroquinoxaline (cas: 5448-43-1Application In Synthesis of 6-Chloroquinoxaline).

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 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.Application In Synthesis of 6-Chloroquinoxaline

Referemce:
Quinoxaline – Wikipedia,
Quinoxaline | C8H6N2 | ChemSpider

Open-Resonance-Assisted Hydrogen Bonds and Competing Quasiaromaticity was written by Nguyen, Yen H.;Lampkin, Bryan J.;Venkatesh, Amrit;Ellern, Arkady;Rossini, Aaron J.;VanVeller, Brett. And the article was included in Journal of Organic Chemistry in 2018.Formula: C8H5ClN2 This article mentions the following:

The delocalization of electron d. upon tautomerization of a proton across a conjugated bridge can alter the strength of hydrogen bonds. This effect has been dubbed resonance-assisted hydrogen bonding (RAHB) and plays a major role in the energetics of the tautomeric equilibrium The goal of this work was to investigate the role that π-delocalization plays in the stability of RAHBs by engaging other isomerization processes. Similarly, acid-base chem. has received little exptl. attention in studies of RAHB, and we address the role that acid-base effects play in the tautomeric equilibrium We find that π-delocalization and the disruption of adjacent aromatic rings is the dominant effect in determining the stability of a RAHB. 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 are important class of heterocyclic compounds, associated with wider pharmacological applications. 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.Formula: C8H5ClN2

Referemce:
Quinoxaline – Wikipedia,
Quinoxaline | C8H6N2 | ChemSpider

Metal & Surfactant-Free oxidation of Quinoxalin-2(1H)-ones: Access to Quinoxaline-2,3-diones was written by Li, Xuan;Zang, Jiawang;Wang, Shoucai;Kang, Chen;Xu, Jiawei;Jiang, Guangbin;Ji, Fanghua. And the article was included in Tetrahedron Letters in 2022.Electric Literature of C8H5BrN2O2 This article mentions the following:

An efficient and direct metal & surfactant-free surfactant-free oxidation of quinoxalin-2(1H)-ones for the construction of 1,4-dihydroquinoxaline-2,3-diones I [R = Me, Et, Bn, etc.; R¹ = H, 7-NO₂, 6-OMe, etc.] was developed. A range of oxidative products are obtained with satisfactory yields (up to 99%). This practical method featured transition metal free, surfactant free, chromatog. free, mild reaction conditions, good functional group tolerance and easy scale-up synthesis. Furthermore, it provided a convenient approach for the synthesis of one kind of known inhibitor for α-glucosidase. This mechanistic study showed that this transformation was not a radical process. In the experiment, the researchers used many compounds, for example, 6-Bromoquinoxaline-2,3(1H,4H)-dione (cas: 1910-90-3Electric Literature of C8H5BrN2O2).

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.Electric Literature of C8H5BrN2O2

Referemce:
Quinoxaline – Wikipedia,
Quinoxaline | C8H6N2 | ChemSpider

Photochemical hydroxylation of quinoxalines was written by Verbeek, J.;Berends, W.;Van Beek, H. C. A.. And the article was included in Recueil des Travaux Chimiques des Pays-Bas in 1976.Reference of 5448-43-1 This article mentions the following:

Irradiation of quinoxaline (I) in acidic aqueous solution under anaerobic conditions gave 5-hydroxyquinoxaline (II) and the 1,4-dihydroquinoxaline radical cation (III). III was characterized by ESR spectroscopy. Under aerobic conditions II is the only irradiation product formed. The effect of substituents attached to the benzene nucleus of I is analyzed. 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. 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.Reference of 5448-43-1

Referemce:
Quinoxaline – Wikipedia,
Quinoxaline | C8H6N2 | ChemSpider

Novel rhodamine dye with large Stokes shifts by fusing the 1,4-diethylpiperazine moiety and its applications in fast detection of Cu²⁺ was written by Gong, Jin;Liu, Chang;Jiao, Xiaojie;He, Song;Zhao, Liancheng;Zeng, Xianshun. And the article was included in RSC Advances in 2020.SDS of cas: 6639-82-3 This article mentions the following:

Rhodamine dyes were widely developed for designing probes due to their excellent photophys. properties and biocompatibility. However, traditional rhodamine dyes still bear major drawbacks of short emission wavelengths (<600 nm) and narrow Stokes shifts (<30 nm), which limit their biol. imaging applications. Herein, the authors reported a novel mitochondria-targeted fluorescent dye JRQ with near-IR (NIR) emission wavelength and improved Stokes shift (63 nm) by tuning the donor-acceptor-donor (D-A-D) character of the rhodamine skeleton. As expected, JRQ exhibited multiple excellent properties and could accumulate in mitochondria, and can therefore be used as a signal reporter for the design of fluorescent probes by taking advantage of the fluorescence controlled mechanism of the ring opening and closing chem. processes of the spirolactone platform. By using JRQ as a precursor, a highly sensitive fluorescent probe JRQN for the fast detection of mitochondrial Cu²⁺ ions was synthesized based on the Cu²⁺-triggered specific hydrolysis mechanism because mitochondria are an important reservoir of intracellular Cu²⁺. The authors expect that the Stokes shift increase of rhodamine dyes via tuning the donor-acceptor-donor (D-A-D) character of the rhodamine skeleton will provide a novel synthetic approach for the development of rhodamine dyes and expansion of their applications. In the experiment, the researchers used many compounds, for example, 6-Methoxyquinoxaline (cas: 6639-82-3SDS of cas: 6639-82-3).

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. 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.SDS of cas: 6639-82-3

Referemce:
Quinoxaline – Wikipedia,
Quinoxaline | C8H6N2 | ChemSpider

12H-[1]Benzopyrano[2,3-b]quinoxalinone synthesis was written by Vinot, Nicole;Maitte, Pierre. And the article was included in Journal of Heterocyclic Chemistry in 1982.Reference of 49679-45-0 This article mentions the following:

3-Benzyl-2-quinoxalinoes (I) were obtained by condensation of o-(H₂N)₂C₆H₄ with phenylpyruvic acids. I were easily substituted in position 2, which permitted the preparation of many derivatives; however, cyclization of I into 12H-[1]benzopyrano[2,3-b]quinoxalines failed. This new hetercycle was synthesized from Et-2-phenoxy-3-quinoxalinecarboxylate. 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. 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.Reference of 49679-45-0

Referemce:
Quinoxaline – Wikipedia,
Quinoxaline | C8H6N2 | ChemSpider