Tag: 100-200

Electronic transitions in the aromatic chlorazines. III. Absorption spectra of monochloro quinoxalines, phthalazines, quinazolines, and cinnolines was written by Favini, Giorgio;Simonetta, Massimo. And the article was included in Gazzetta Chimica Italiana in 1960.Synthetic Route of C8H5ClN2 This article mentions the following:

The absorption spectra of 2-, 5-, and 6-chloroquinoxalines (I, II, III), 2-, 4-, and 6-chloroquinazolines (IV, V, VI), 1-, 5-, and 6-chlorophthalazines (VII, VIII, IX), and 3-, and 4-cinnolines (X, XI) were measured in isoöctane and in MeOH between 220 and 450 mμ. Condensation of o-(H₂N)₂C₆H₄ and OC(CO₂Et)₂ and hydrolysis, decarboxylation of the 2-hydroxyquinoxaline-3-carboxylic acid and chlorination with POCl₃ gave I, m. 46-7° (C₅H₁₂). Acetylation of o-ClC₆H₄NH₂ and nitration with fuming HNO₃, deacetylation of the crystalline 2,6-Cl-(O₂N)C₆H₃NHAc with NaOH, reduction with SnCl₂, and condensation of the reduction product with OHCCHO.(NaHSO₃)₂ yielded II, m. 61-2° (petr. ether). Similarly, com. 4,2-Cl(H₂N)C₆H₃NH₂ was transformed to III, m. 63-4° (petr. ether). Reduction of o-O₂NC₆H₄CHO, condensation with urea, and chlorination of the 2-quinazolone with PCl₃ and POCl₃ gave IV, m. 108° (ligroine). HCONH₂ condensed with o-H₂NC₆H₄CO₂H and the 4-quinazolone chlorinated with PCl₅ and POCl₃ successively yielded V, m. 99-100° (petr. ether). Nitration of 3-ClC₆H₄CHO and condensation with HCONH₂ followed by reduction with Zn in AcOH gave VI, m. 145° (dilute alc.). Phthalide transformed through the Br derivative into o-OHCC₆H₄CO₂H, condensed with N₂H₄.H₂O to the phthalazone and chlorinated with POCl₃ yielded VII, m. 110-11° (ligroine). Conversion of 3,4-Me₂C₆H₃NH₂ by the Sandmeyer reaction gave 10 g. 3,4-Me₂C₆H₃Cl, converted through 3,4-(CHBr₂)₂C₆H₃Cl to 3,4-(OHC)₂C₆H₃Cl and condensed with N₂H₄ to yield 0.4 g. IX, m. 132°. α-Tetrahydronaphthylamine (5 g.) converted according to Sandmeyer to α-chlorotetrahydronaphthalene and submitted to oxidative degradation, the isomeric mixture condensed with N₂H₄, the product chlorinated with POCl₃ and the mixture of dichlorophthalazines (0.2 g.) treated with HI and P to eliminate the Cl of the heterocyclic ring gave a small amount of VIII. HCN added to o-O₂NC₆H₄CHO and the nitrile saponified, the NO₂ group reduced catalytically and the acid diazotized, reduced with SnCl₂ and the 3-hydroxycinnoline chlorinated with POCl₃ gave X, m. 90-1° (ligroine). MeCOPh nitrated and reduced with Sn and HCl, the o-H₂NC₆H₄COMe diazotized and transformed into 4-hydroxycinnoline, treated successively with PCl₅ and POCl₃, and recrystallized from ligroine gave XI, m. 78-9°. The nature of the bands observed and the infuence exerted on the absorption maximum by introduction of an atom of Cl into the benzodiazine structure were discussed. In the experiment, the researchers used many compounds, for example, 6-Chloroquinoxaline (cas: 5448-43-1Synthetic Route 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. 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 C8H5ClN2

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.Name: 6-Methoxyquinoxaline 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-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. 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.Name: 6-Methoxyquinoxaline

Referemce:
Quinoxaline – Wikipedia,
Quinoxaline | C8H6N2 | ChemSpider

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

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

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

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

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

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

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

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