Heterocyclic Building Blocks-quinoxaline

Teng, Min’s team published research in Bioorganic & Medicinal Chemistry Letters in 2007-10-01 | CAS: 25983-14-6

Bioorganic & Medicinal Chemistry Letters published new progress about Homo sapiens. 25983-14-6 belongs to class quinoxaline, name is 2,3,6,7-Tetrachloroquinoxaline, and the molecular formula is C8H2Cl4N2, Formula: C8H2Cl4N2.

Teng, Min published the artcileSmall molecule ago-allosteric modulators of the human glucagon-like peptide-1 (hGLP-1) receptor, Formula: C8H2Cl4N2, the main research area is dichloroquinoxaline derivative preparation structure glucagon peptide hGLP1 receptor modulator.

Following the previous publication describing the biol. profiles, the authors herein describe the structure-activity relationships of a core set of quinoxalines as the hGLP-1 receptor agonists. The most potent and efficacious compounds are 6,7-dichloroquinoxalines bearing an alkyl sulfonyl group at the C-2 position and a secondary alkyl amino group at the C-3 position. These findings serve as a valuable starting point for the discovery of more drug-like small mol. agonists for the hGLP-1 receptor.

Referemce:
Quinoxaline – Wikipedia,
Quinoxaline | C8H6N2 | ChemSpider

Inoue, Mami’s team published research in European Journal of Organic Chemistry in 2019 | CAS: 39267-05-5

European Journal of Organic Chemistry published new progress about Epoxidation, stereoselective. 39267-05-5 belongs to class quinoxaline, name is 2,3-Dichloro-6-methylquinoxaline, and the molecular formula is C9H6Cl2N2, Formula: C9H6Cl2N2.

Inoue, Mami published the artcileInherently Chiral Cavitand Curvature: Diastereoselective Oxidation of Tethered Allylsilanes, Formula: C9H6Cl2N2, the main research area is chiral cavitand tethered allylsilane preparation stereoselective oxidation; epoxide chiral cavitand tethered silane preparation.

Syntheses of inwardly and outwardly directed allylsilanes those are tethered to new inherently chiral cavitands are described. Oxidized with mCPBA, these allylsilanes result in diastereomeric mixtures of epoxide mols. Thus, it enables the authors to have comparative study of cavitand-structure diastereoselectivity relation, which revealed that an inward allylsilane group flanked by a dibenzo[f, h]quinoxaline and two bridged methylene groups have the best chem. yield and diastereoselection.

Referemce:
Quinoxaline – Wikipedia,
Quinoxaline | C8H6N2 | ChemSpider

Liu, Yunkui’s team published research in Journal of Organic Chemistry in 2013-02-01 | CAS: 40353-41-1

Journal of Organic Chemistry published new progress about Aryl aldehydes, heteroaryl Role: SPN (Synthetic Preparation), PREP (Preparation) (quinoxalinyl). 40353-41-1 belongs to class quinoxaline, name is 2-(Thiophen-2-yl)quinoxaline, and the molecular formula is C12H8N2S, Product Details of C12H8N2S.

Liu, Yunkui published the artcileMultifold Bond Cleavage and Formation between MeOH and Quinoxalines (or Benzothiazoles): Synthesis of Carbaldehyde Dimethyl Acetals, Product Details of C12H8N2S, the main research area is quinoxaline methanol potassium persulfate cross coupling; quinoxalinyl carbaldehyde dimethyl acetal preparation green chem; benzothiazole methanol potassium persulfate cross coupling; benzothiazolyl carbaldehyde dimethyl acetal preparation green chem.

A K2S2O8-mediated direct cross-coupling of quinoxalines (or benzothiazoles) with methanol leading to 2-quinoxalinyl (or 2-benzothiazolyl) carbaldehyde di-Me acetals has been achieved. 2-Quinoxalinyl carbaldehyde di-Me acetals were readily converted into 2-quinoxalinyl carbaldehydes in good to excellent yields under acidic conditions. Preliminary mechanistic studies suggest that the reaction proceeds via multifold bond cleavage and formation between methanol and N-heterocycles involving a dioxygen-participated radical process. This method allows for the synthesis of a variety of 2-quinoxalinyl (or 2-benzothiazolyl) carbaldehyde di-Me acetals directly via cross-coupling of simple N-heterocyclic C-H bond and methanol under aldehyde-, acid-, and transition-metal-free conditions.

Referemce:
Quinoxaline – Wikipedia,
Quinoxaline | C8H6N2 | ChemSpider

Isoda, Kyosuke’s team published research in ChemistrySelect in 2017 | CAS: 25983-14-6

ChemistrySelect published new progress about Dipole moment. 25983-14-6 belongs to class quinoxaline, name is 2,3,6,7-Tetrachloroquinoxaline, and the molecular formula is C8H2Cl4N2, Product Details of C8H2Cl4N2.

Isoda, Kyosuke published the artcileDipole-Driven Self-Organization of Liquid-Crystalline N-Heteroacene Derivatives Showing Redox-Properties, Product Details of C8H2Cl4N2, the main research area is dichloro trimethyldodecyloxytetraazanaphthacene preparation liquid crystal phase transition redox.

An introduction of halogen atoms to liquid-crystalline (LC) TANC derivatives to tune their electronic characters as well as the charge polarization on π-conjugated N-heteroacene framework was reported. The electroneg. Cl atoms can improve the electron-accepting property of LC TANC. Also, the induced charge polarization due to the substitution of Cl atoms generated an intrinsic dipole moment on π-conjugated N-heteroacene framework, which was able to serve as a driving force for stabilizing self-organization of N-heteroacene mols. in thin films.

Referemce:
Quinoxaline – Wikipedia,
Quinoxaline | C8H6N2 | ChemSpider

Lindner, Benjamin D.’s team published research in Chemistry – A European Journal in 2012 | CAS: 25983-14-6

Chemistry – A European Journal published new progress about Aryl fluorides Role: PRP (Properties), RCT (Reactant), SPN (Synthetic Preparation), RACT (Reactant or Reagent), PREP (Preparation). 25983-14-6 belongs to class quinoxaline, name is 2,3,6,7-Tetrachloroquinoxaline, and the molecular formula is C8H2Cl4N2, Formula: C8H2Cl4N2.

Lindner, Benjamin D. published the artcileSynthesis and Optical Properties of Diaza- and Tetraazatetracenes, Formula: C8H2Cl4N2, the main research area is diazatetracene tetraazatetracene preparation optical property.

A series of functionalized diaza- and tetraazatetracenes was synthesized, either by condensation of an aromatic diamine with an ortho-quinone/diethyloxalate followed by chlorination with POCl3 to give diazatetracenes or by palladium-catalyzed coupling of a phenylenediamine with various 2,3-dichloroquinoxalines to give tetraazatetracenes (after oxidation with MnO2). Representative examples included halogenated and nitrated derivatives The optical properties of these azatetracenes were discussed with respect to their mol. structures and substitution patterns. The diazatetracenes and tetraazatetracenes formed two different groups that had significantly different electronic structures and properties. Furthermore, 1,2,3,4-tetrafluoro-6,11-bis((triisopropylsilyl)ethynyl)benzo[b]phenazine was synthesized, which is the first reported fluorinated diazatetracene. Single-crystal X-ray anal. of this compound is reported.

Referemce:
Quinoxaline – Wikipedia,
Quinoxaline | C8H6N2 | ChemSpider

Thompson, Andrew J.’s team published research in ChemMedChem in 2013 | CAS: 25983-14-6

ChemMedChem published new progress about 5-HT3 receptors Role: BSU (Biological Study, Unclassified), BIOL (Biological Study) (5-HT3AB). 25983-14-6 belongs to class quinoxaline, name is 2,3,6,7-Tetrachloroquinoxaline, and the molecular formula is C8H2Cl4N2, Name: 2,3,6,7-Tetrachloroquinoxaline.

Thompson, Andrew J. published the artcileStructure-Activity Relationships of Quinoxaline-Based 5-HT3A and 5-HT3AB Receptor-Selective Ligands, Name: 2,3,6,7-Tetrachloroquinoxaline, the main research area is quinoxaline preparation serotonin 5HT3 subtype receptor selective ligand.

Until recently, discriminating between homomeric 5-HT3A and heteromeric 5-HT3AB receptors was only possible with ligands that bind in the receptor pore. This study describes the first series of ligands that can discriminate between these receptor types at the level of the orthosteric binding site. During a recent fragment screen, 2-chloro-3-(4-methylpiperazin-1-yl)quinoxaline (VUF10166) was identified as a ligand that displays an 83-fold difference in [3H]granisetron binding affinity between 5-HT3A and 5-HT3AB receptors. Fragment hit exploration, initiated from VUF10166 and 3-(4-methylpiperazin-1-yl)quinoxalin-2-ol, resulted in a series of compounds with higher affinity at either 5-HT3A or 5-HT3AB receptors. These ligands reveal that a single atom is sufficient to change the selectivity profile of a compound At the extremes of the new compounds were 2-amino-3-(4-methylpiperazin-1-yl)quinoxaline (I), which showed 11-fold selectivity for the 5-HT3A receptor, and 2-(4-methylpiperazin-1-yl)quinoxaline, which showed an 8.3-fold selectivity for the 5-HT3AB receptor. These compounds represent novel mol. tools for studying 5-HT3 receptor subtypes and could help elucidate their physiol. roles.

Referemce:
Quinoxaline – Wikipedia,
Quinoxaline | C8H6N2 | ChemSpider

Bouanane, Zohra’s team published research in Journal of Molecular Structure in 2017-07-05 | CAS: 39267-05-5

Journal of Molecular Structure published new progress about Counterions (counterion effect on catecholase activity). 39267-05-5 belongs to class quinoxaline, name is 2,3-Dichloro-6-methylquinoxaline, and the molecular formula is C9H6Cl2N2, Safety of 2,3-Dichloro-6-methylquinoxaline.

Bouanane, Zohra published the artcileSynthesis, structural, catecholase, tyrosinase and DFT studies of pyrazoloquinoxaline derivatives, Safety of 2,3-Dichloro-6-methylquinoxaline, the main research area is pyrazolylquinoxaline derivative preparation copper ligand catecholase activity; mol structure pyrazolylquinoxaline copper complex DFT; electronic structure pyrazolylquinoxaline copper complex DFT.

Six functional multidentate ligands: 2,3-bis(3,5-dimethyl-1H-pyrazol-1-yl) quinoxaline L1, 2,3-bis(3,5-dimethyl-1H-pyrazol-1-yl)-6-nitroquinoxaline L2, 2,3-bis(3,5-dimethyl-1H-pyrazol-1-yl)-6-methylquinoxaline L3, 2-(3,5-dimethyl-1H-pyrazol-1-yl)-3-hydrazinyl-6-nitroquinoxaline L4, 2-chloro-3-(3,5-dimethyl-1H-pyrazol-1-yl)-6-methylquinoxaline L5, 2-chloro-3-(3,5-dimethyl-1H-pyrazol-1-yl)quinoxaline L6, (I – VI) and a new copper (II) complex (VII) , were prepared and evaluated for their catecholase activities at aerobic conditions. We found that, the reaction rate depends on: the nature of the substituents in the quinoxaline ring, counter anion, metal, concentration of ligand and the used solvent. The complex obtained in-situ from reaction of one equivalent of ligand L1 and two equivalent of Cu(CH3COO)2 in methanol showed the highest oxidation rate activity (V = 33.48 μmol L-1. min-1). In addition, geometry optimizations of the complexes in order to get better insight into the geometry and the electronic structure and chem. reactivity were carried out by means of DFT calculations

Referemce:
Quinoxaline – Wikipedia,
Quinoxaline | C8H6N2 | ChemSpider

Perkampus, H. H. et al. published their research in Zeitschrift fuer Naturforschung in 1962 |CAS: 62163-09-1

5-Chloroquinoxaline(cas:62163-09-1) belongs to quinoxaline. The antitumoral properties of quinoxaline compounds have been of interest. Recently, quinoxaline and its analogs have been investigated as the catalyst’s ligands. Synthetic Route of 62163-09-1

Perkampus, H. H. published an article in 1962, the title of the article was Ultraviolet absorption spectra of some simple quinoxaline derivatives.Synthetic Route of 62163-09-1 And the article contains the following content:

The UV spectra of the following quinoxaline derivatives were investigated in different solvents: 2-Me-, 2-Cl-, 2-MeO-. 2,3-di-Me-, 2,3-di-MeO-, 2,3-di-isopropoxy-, 2,3-di-Cl-, 2,3-di-Br-, 5- and 6-Me, 5- and 6-Cl, and 6,7-di-Me. Position, intensity, and assignment of the absorption bands and the fine structure of the 1Lb band are tabulated. The experimental process involved the reaction of 5-Chloroquinoxaline(cas: 62163-09-1).Synthetic Route of 62163-09-1

Referemce:
Quinoxaline – Wikipedia,
Quinoxaline | C8H6N2 | ChemSpider

Jumal, Juliana et al. published their research in AIP Conference Proceedings in 2018 |CAS: 34413-35-9

5,6,7,8-Tetrahydroquinoxaline(cas:34413-35-9) belongs to quinoxaline. 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 34413-35-9

On June 5, 2018, Jumal, Juliana; Ayomide, Adetunji Fridaos published an article.Related Products of 34413-35-9 The title of the article was Synthesis and radical scavenging activity of 6-hydroxyl-4-methylcoumarin and its derivatives. And the article contained the following:

Four compounds of coumarin derivatives namely 6-hydroxyl-4-methylcoumarin (I), 6-hydroxyl-4-methyl-5-(p-nitrophenyl azocoumarin) (II), 6-hydroxyl-4-methyl-5,7-(bis-p-nitrophenyl azocoumarin) (III) and 6-hydroxyl-4-methyl-5,7-(bis-p-chlorophenyl azocoumarin) (IV) were successfully synthesized. These compounds were prepared by reacting hydroquinone with ethylacetoacetate and selected anilines which are chloro and nitro aniline. All synthesized compounds were characterized by CHN micro-elemental anal., 1H NMR (NMR) and Fourier Transform IR (FTIR) spectroscopic methods. The IR spectra of these compounds exhibited five important stretching vibrations: (-OH), (C=O), (C=C), (C-O) and (C-N) at 3441-3359 cm-1, 1604-1632 cm-1, 1581-1496 cm-1, 1331-1225 cm-1, 1251-1109 cm-1, resp. 1H NMR spectra of these compounds show the presence of proton aromatic, proton Me and proton pyrone ring with the chem. shift at δH 7.00-8.70 ppm, δH 2.20-2.50 ppm and δH 6.10-6.90 ppm, resp. CHN anal. results of all compounds are in good agreement with the calculated values. All the synthesized compounds were evaluated for their antioxidant activity using DPPH method and ascorbic acid used as the standard UV-Vis spectroscopic technique was used to investigate the absorbance of these compounds Compound (II) shows high antioxidant activities compared to compound (I), (III) and (IV) which show moderate to low activities. The experimental process involved the reaction of 5,6,7,8-Tetrahydroquinoxaline(cas: 34413-35-9).Related Products of 34413-35-9

Referemce:
Quinoxaline – Wikipedia,
Quinoxaline | C8H6N2 | ChemSpider

Landquist, Justus K. et al. published their research in Journal of the Chemical Society in 1953 |CAS: 62163-09-1

Landquist, Justus K. published an article in 1953, the title of the article was Quinoxaline N-oxides. I. The oxidation of quinoxaline and its Bz-substituted derivatives.Application of 62163-09-1 And the article contains the following content:

Quinoxaline (I) and its Bz-substituted-alkyl, alkoxy, halo, and acylamino derivatives are oxidized to 1- and 1,4-dioxides by organic peroxy acids. Resistance to N-oxidation is encountered in 5- and 8-substituted I. Reduction of 2,3-(O2N)2C6H3OEt with H and Raney Ni gave 3,1,2-EtOC6H3(NH2)2, oil (picrate, m. 210-12°). 2,4-Br(O2N)C6H3Me nitrated with HNO3 and H2SO4 at 40-5° gave 2,4,5-Br(O2N)2C6H2Me, m. 94-5°, which, treated with NH3 in alc. 5 h. at 120° and then reduced with Zn dust and NaOH in EtOH, yielded the 4,5-(H2N)2 analog, m. 140-1°. The following general procedure for preparation of I derivatives was used: (CHO.NaHSO3)2, an ο-phenylenediamine, and H2O were stirred 3 h. at 60°, then made alk. with KOH, and the I derivative was filtered off. The following derivatives were prepared (substituent, m.p., m.p. of 1-oxide, m.p. of 1,4-dioxide): 5-Me, 20-1°, b15, 120°, 131-2°, 192-4°; 5-EtO, 63-4°, b18 165-6°, 114-16°, -; 5-Cl (II), 60-2°, 177-9°, -; 6-iodo, 114-15°, -, -; 6-NC (III), 176-8°, -, -; 6,7-Me2, 100-1°, -, 220°; 6,7-benzo, 125-6°, -, -; 6,7-ClMe (IV), 120-2°, 166-8°, 227°; 6,7-BrMe (V), 127-8°, 167-8°, 222-4°; 6,7-Cl2 (VI), 210°, -, 206-8°; 5,8-Cl2 (VII), 205-7°, -, -; 6-Br (VIII)(prepared by the Sandmeyer reaction from the 6-NH2 compound), 48-9°, b18 146-9°, -, 223-5°; 6-AcNH (prepared from the 6-NH2 compound with Ac2O), 196.5°, -, 245-7°; 5-AcNH, -, 175-8°, 230-2° (insufficient for anal.). The following N-oxides were also prepared (substituent, m.p. 1-oxide, m.p. 1,4-dioxide): 6-Me (IX), -, 218-19°; 5,6-benzo, 158-9°, 215-16°; 5,6:7,8-dibenzo, 243-4°, -; 5-MeO, -, 222°; 6-MeO, -, 227-8°; 6-EtO, -, 192-4°; 5,6-(MeO)2, 138-40°, 220-2°; 6,7-(MeO)2, -, 264-5°; 2-Cl, 150-2°, -; 6-Cl (X), 151-2°, 211-12°. I is oxidized with equimolar AcO2H to quinoxaline 1-oxide, m. 122-3° (XI) while excess peroxy acid yields quinoxaline 1,4-dioxide, m. 241-3° (XII). Simultaneous with N-oxide formation there were obtained 2,3-dihydroxyquinoxalines which are listed below: (substituent, % yield, m.p.): IX, 1, 112°; II, 30, 142-3°; X, 15-30, 144°; VIII, 28, 132°; VII, 65, 160-1°; VI, 43, 170-70.5°; IV, 10, 172-3°; V, 12-6, 160-1°; III, 50, -; 6-O2N, 60, 150°. XI and MeI in MeCN set aside in the dark 36 h., precipitated 1-methylquinoxalinium iodide 4-oxide, m. 188-9°. XI was added cautiously to POCl3, and the mixture boiled 15 min. after the reaction subsided, poured on ice, made alk. with KOH, extracted with Et2O, and concentrated to yield 2-chloroquinoxaline, m. 46-8°. Under similar conditions XII yielded 2,3-dichloroquinoxaline; 5-methylquinoxaline 1-oxide gave 2-chloro-5-methylquinoxaline, m. 95°; and 5,6-benzoquinoxaline 1-oxide yielded 2-chloro-5,6-benzoquinoxaline, m. 120.5°. 2-C10H7NHCH2CO2Et dissolved treated in EtOH with PhN2Cl yielded 1,2-Ph2NC10H6NHCH2CO2Et, m. 135-6°, hydrogenated with Raney Ni at 60° and 50 atm. to 1,2,3,4-tetrahydro-2-oxo-7,8-benzoquinoxaline (XIII), m. 197-8°. XIII with alk. H2O2 gave 2-hydroxy-7,8-benzoquinoxaline, isolated as the hydrate, m. 275-5.5°, which was converted with POCl3 into 2-chloro-7,8-benzoquinoxaline, m. 128-9°. N-(6-nitro-o-tolyl)glycine in EtOH hydrogenated over Raney Ni at 60° and 60 atm. yielded 1,2,3,4-tetrahydro-5-methyl-2-oxoquinoxaline, m. 177-80°, readily oxidized to 2-hydroxy-5-methylquinoxaline, m. 282-3°. 2-Chloro-7,8-benzoquinoxaline and piperidine refluxed 1.5 h. gave 2-piperidino-7,8-benzoquinoxaline, m. 101.5-2.5°. 2-Piperidino-5,6-benzoquinoxaline, m. 124-5°, was similarly prepared Cl slowly passed 1 h. into 5,6-benzoquinoxaline in glacial HOAc, and the solution filtered and diluted with H2O yielded, on purification, dichloro-5,6-benzoquinoxaline, m. 187-8°. Methylation of 2,3-dihydroxy-6-nitroquinoxaline with Me2SO4 gave 3-hydroxy-1-methyl-6(or 7)-nitro-2(1H)-quinoxalinone, m. 344°. 6(or 7)-Cyano-3-hydroxy-1-methyl-2(1H)-quinoxalinone, m. 353-4°, is similarly prepared The experimental process involved the reaction of 5-Chloroquinoxaline(cas: 62163-09-1).Application of 62163-09-1

Referemce:
Quinoxaline – Wikipedia,
Quinoxaline | C8H6N2 | ChemSpider