Heterocyclic Building Blocks-quinoxaline

The thermolysis of polyazapentadienes. Part 2. Formation of quinoxalines from 5-aryl-1-phenyl-1,2,5-triazapentadienes was written by McNab, Hamish. And the article was included in Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999) in 1982.Formula: C9H8N2O This article mentions the following:

Gas phase pyrolysis of RC₆H₄N:CHCH:NNHPh (I; R = p-Me, -OMe, -Cl, -Ac) at 600° and 10^-2 Torr gave the quinoxalines II (R = Me, OMe, Cl, Ac, R¹ = H) in 13-42% yield. Similarly, I (R = o-Me, -OMe, -Cl) gave II (R = H, R¹ = Me, OMe, Cl) but in lower yields; II (R = R¹ = H) was the major by-product due to ipso attack and elimination of the substituent. Meta-substituted I gave mixtures of 5- and 6-substituted quinoxalines on pyrolysis. The 5-isomer is dominant for compounds with meta-alkyl substituents whereas the 6-isomer is the major product for those with electron-withdrawing or -donating meta-substituents. 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. 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.Formula: C9H8N2O

Referemce:
Quinoxaline – Wikipedia,
Quinoxaline | C8H6N2 | ChemSpider

(DPEPhos)Ni(mesityl)Br: An Air-Stable Pre-Catalyst for Challenging Suzuki-Miyaura Cross-Couplings Leading to Unsymmetrical Biheteroaryls was written by Sawatzky, Ryan S.;Stradiotto, Mark. And the article was included in Synlett in 2018.Recommanded Product: 5448-43-1 This article mentions the following:

The successful application of (DPEPhos)Ni(mesityl)Br as a pre-catalyst in the Suzuki-Miyaura cross-coupling of heteroaryl chlorides or bromides and heteroaryl boronic acids is reported. The use of (DPEPhos)Ni(mesityl)Br in this context allows for such reactions to be conducted under mild conditions (2 mol% Ni, 25 °C), including cross-couplings leading to unsym. biheteroaryls. Successful transformations of this type involving problematic pyridinyl boronic acid substrates (10 mol% Ni, 60 °C) are also described. 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. 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.Recommanded Product: 5448-43-1

Referemce:
Quinoxaline – Wikipedia,
Quinoxaline | C8H6N2 | ChemSpider

A spiropyran with low pK_a for tracking DNA G-quadruplexes and revealing the dissipation of ΔΨm with senescence using an in-situ switching strategy was written by Tian, Xinrong;Li, Jin;Zhang, Yanhui;Gao, Ying;Afzal, Muhammad Wasim;Wang, Aoli;James, Tony D.;Bai, Yinjuan;Guo, Yuan. And the article was included in Sensors and Actuators, B: Chemical in 2022.SDS of cas: 6639-82-3 This article mentions the following:

The in-situ fluorescence triggering of bioprobes only using endogenous bioforces is an ideal non-destructive real-time detection method, which is of particular interest to improve the accuracy of clin. diagnosis and treatment. We have recently reported a strategy of spiropyran in-situ switching triggered by endogenous biol. forces in vivo to develop optical probes for this purpose. However, such probes, as with all spiropyrans, are sensitive to lysosomal acidity. We here present a spiropyran-based fluorescent probe TANG with low pKa, which can recognize intranuclear DNA G4s in situ without the aid of exogenous light or chems. and is as stable to lysosomal acidity due to a decreased pKa value (4.3). Interestingly, despite the stability to lysosomal pH environment, the TANG spiropyran can be opened in situ by the neg. membrane potential of extranuclear mitochondria (ΔΨm), causing a ratiometric change in fluorescence signals and providing the in-situ and real-time tracking of ΔΨm. Of note, ratiometric imaging using TANG indicates that ΔΨm decreases gradually with cellular senescence, which is to the best of our knowledge the first visualization of such mitochondrion-related aging processes using a ratiometric imaging approach. 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. 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. 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: 6639-82-3

Referemce:
Quinoxaline – Wikipedia,
Quinoxaline | C8H6N2 | ChemSpider

Mechanistic Insight into Copper-Mediated Trifluoromethylation of Aryl Halides: The Role of CuI was written by Liu, He;Wu, Jian;Jin, Yuxuan;Leng, Xuebing;Shen, Qilong. And the article was included in Journal of the American Chemical Society in 2021.Quality Control of Ethyl 3-chloroquinoxaline-2-carboxylate This article mentions the following:

The synthesis, characterization, and reactivity of key intermediates [Cu(CF₃)(X)]^–Q⁺ (X = CF₃ or I, Q = PPh₄) in copper-mediated trifluoromethylation of aryl halides were studied. Qual. and quant. studies showed [Cu(CF₃)₂]^–Q⁺ and [Cu(CF₃)(I)]^–Q⁺ were not highly reactive. Instead, a much more reactive species, ligand-less [CuCF₃] or DMF-ligated species [(DMF)CuCF₃], was generated in the presence of excess CuI. On the basis of these results, a general mechanistic map for CuI-promoted trifluoromethylation of aryl halides was proposed. Furthermore, on the basis of this mechanistic understanding, a HOAc-promoted protocol for trifluoromethylation of aryl halides with [Ph₄P]⁺[Cu(CF₃)₂]^– was developed. In the experiment, the researchers used many compounds, for example, Ethyl 3-chloroquinoxaline-2-carboxylate (cas: 49679-45-0Quality Control of Ethyl 3-chloroquinoxaline-2-carboxylate).

Ethyl 3-chloroquinoxaline-2-carboxylate (cas: 49679-45-0) belongs to quinoxaline derivatives. Quinoxalines are important class of heterocyclic compounds, associated with wider pharmacological applications. 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 Ethyl 3-chloroquinoxaline-2-carboxylate

Referemce:
Quinoxaline – Wikipedia,
Quinoxaline | C8H6N2 | ChemSpider

Biomass into chemicals: One-pot two- and three-step synthesis of quinoxalines from biomass-derived glycols and 1,2-dinitrobenzene derivatives using supported gold nanoparticles as catalysts was written by Climent, M. J.;Corma, A.;Hernandez, J. C.;Hungria, A. B.;Iborra, S.;Martinez-Silvestre, S.. And the article was included in Journal of Catalysis in 2012.Quality Control of 6-Chloroquinoxaline This article mentions the following:

An efficient and selective one-pot two-step method, for the synthesis of quinoxalines by oxidative coupling of vicinal diols with 1,2-phenylenediamine derivatives, has been developed by using gold nanoparticles supported on nanoparticulated ceria (Au/CeO₂) or hydrotalcite (Au/HT) as catalysts and air as oxidant, in the absence of any homogeneous base. Reaction kinetics shows that the reaction controlling step is the oxidation of the diol to α-hydroxycarbonyl compound Furthermore, a one-pot three-step synthesis of 2-methylquinoxaline starting from 1,2-dinitrobenzene and 1,2-propanediol has been successfully carried out with 98% conversion and 83% global yield to the final product. In the experiment, the researchers used many compounds, for example, 6-Chloroquinoxaline (cas: 5448-43-1Quality Control of 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. 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.Quality Control of 6-Chloroquinoxaline

Referemce:
Quinoxaline – Wikipedia,
Quinoxaline | C8H6N2 | ChemSpider

Ni-nanoparticles: An efficient catalyst for the synthesis of quinoxalines was written by Kumar, Ajeet;Kumar, Santosh;Saxena, Amit;De, Arnab;Mozumdar, Subho. And the article was included in Catalysis Communications in 2008.Product Details of 5448-43-1 This article mentions the following:

Biol. active quinoxalines were efficiently synthesized in excellent yields and in less reaction time using inexpensive, monodispersed and easily recyclable Ni-nanoparticles. In order to elucidate the role of the Ni-nanoparticles, a control reaction was conducted using glyoxal and o-phenylenediamine in acetonitrile in the absence of Ni-nanoparticles. Quinoxaline was formed in around 10 h with a 30% yield. However, the same reaction carried out in acetonitrile using 10 mol.% of Ni-nanoparticles (14-18 nm) at 25° and stirred under N₂ gave quinoxaline in quant. yield in 10 min. The separation of the product was facile and the catalyst could be separated and recycled by mild centrifugation. This method is very quick, avoids the use of expensive reagents, high temperatures (the reaction takes place at room temperature) and leads to excellent yield. 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. 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.Product Details of 5448-43-1

Referemce:
Quinoxaline – Wikipedia,
Quinoxaline | C8H6N2 | ChemSpider

An unexpected ring-opening in the Reissert reaction on 2,3-diphenylquinoxaline N-oxide was written by Nasielski, J.;Heilporn, S.;Nasielski-Hinkens, R.;Tinant, B.;Declercq, J. P.. And the article was included in Tetrahedron in 1989.SDS of cas: 5448-43-1 This article mentions the following:

When quinoxaline-N-oxide is reacted with KCN and BzCl in H₂O or MeOH; the products are 2-, 5- and 6-chloroquinoxaline and small amounts of 2-cyanoquinoxaline. Using three equivalent of Me₃SiCN instead of KCN, and CH₂Cl₂ as the solvent, leads to a 72% yield of 2-cyanoquinoxaline. The reaction of Me₃SiCN and BzCl with 2,3-diphenylquinoxaline-N-oxide leads to 2-Bz₂NC₆H₄N:CPhCN (I). The structure of I is based on spectroscopic data and on an X-ray crystallog. anal. 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. 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.SDS of cas: 5448-43-1

Referemce:
Quinoxaline – Wikipedia,
Quinoxaline | C8H6N2 | ChemSpider

Substituent effect on local aromaticity in mono and di-substituted heterocyclic analogs of naphthalene was written by Mohajeri, Afshan;Shahamirian, Mozhgan. And the article was included in Journal of Physical Organic Chemistry in 2010.Reference of 5448-43-1 This article mentions the following:

A quant. study on local aromaticity has been performed on a series of mono- and di-substituted biheterocycles (quinoline, isoquinoline, quinoxaline, quinazoline). Three electronically based indexes (PDI, ATI, and FLU) have been employed to investigate the substituent effect on the π-electron delocalization in both heterocycle and benzenoid rings. Three typical substituents (Cl, OCH₃, and CN) with different inductive and resonance power have been selected. Generally, substituent causes a reduction in aromaticity irresp. of whether it is electron attracting or electron donating. It is shown that the maximum aromaticity exhibits a similar trend of Cl > CN > OCH₃ for all the studied rings. Moreover, it is found that the substituent situation with respect to the heteroatom has a significant influence on the aromaticity. It results from our study that in di-substituted derivatives, irresp. of whether the two substituents form a meta or para isomer, they preferably choose the position which leads to the maximum aromaticity character. Copyright © 2009 John Wiley & Sons, Ltd. 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

New 5-HT₃ antagonists. Synthesis and preliminary biological activity of 3-substituted 2-piperazinylquinoxalines was written by Monge, Antonio;Palop, Juan;Del Castillo, Juan Carlos;Romero, Gonzalo;Lasheras, Berta;Del Rio, Joaquin;Caldero, Jose Maria;Bosch, Ana;Roca, Juan. And the article was included in Anales de la Real Academia de Farmacia in 1994.Synthetic Route of C11H9ClN2O2 This article mentions the following:

Piperazinylquinoxalines I (R¹ = Cl, CO₂Et, Ph, Cl, CONH₂, NMe₂, R² = H, Et) were prepared and their 5-HT₃ receptor antagonist activity evaluated. The results show that substitution at position 2 of the quinoxaline ring is not a determining factor for the biol. activity. Nevertheless, these compounds show partial agonist or antagonist activity. 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. 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 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.Synthetic Route of C11H9ClN2O2

Referemce:
Quinoxaline – Wikipedia,
Quinoxaline | C8H6N2 | ChemSpider

A novel near-infrared fluorescent probe for rapid detection of peroxynitrite with large stokes shift and imaging in living cells was written by Parthiban, C.;Manivannan, R.;Son, Young-A.. And the article was included in Journal of Photochemistry and Photobiology, A: Chemistry in 2022.Name: 6-Methoxyquinoxaline This article mentions the following:

Peroxynitrite (ONOO^–) plays an essential role in pathol. and physiol. processes like signal transduction, antibacterial activity, etc. Imagining ONOO- in the living system is more important to monitor their function. We have analyzed various coumarin derivatives using DFT computations. We have designed and synthesized a coumarin chalcone-hybrid (Coumn-pHP-ONOO^–) based turn-on NIR fluorescent probe for the rapid detection of ONOO^– based on oxidative hydrolysis of aryl boronate group in a living system. Our probe Coumn-pHP-ONOO^– shows sensitive and selective detection of ONOO^– in the presence of various reactive species with a large stokes shift (149 nm) in THF/Water (6/4, volume/volume, pH = 7.4) solution and rapid response (<5s). The detection limit of the probe is 53.8 nM level and has a reasonable specificity in the presence of other reactive oxygen species. Moreover, our probe Coumn-pHP-ONOO^– displays low toxicity, good biocompatibility, excellent permeability, and it successfully detects the ONOO^– in HeLa cell. 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 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.Name: 6-Methoxyquinoxaline

Referemce:
Quinoxaline – Wikipedia,
Quinoxaline | C8H6N2 | ChemSpider