28082-82-8

Usage

Uses

Used in Pharmaceutical Research:
6,7-DIMETHYL-2(1H)-QUINOXALINONE is used as a potential pharmacophore for the development of new drugs, targeting the treatment of various diseases such as cancer, diabetes, and neurological disorders. Its unique structure and properties make it a valuable candidate for drug discovery and design.
Used in Organic Synthesis:
In the field of organic synthesis, 6,7-DIMETHYL-2(1H)-QUINOXALINONE serves as a key building block, enabling the creation of more complex molecules and compounds with diverse applications.
Used in Biochemical and Biophysical Applications:
6,7-DIMETHYL-2(1H)-QUINOXALINONE has been studied for its potential use as a fluorescent dye, which can be utilized in various biochemical and biophysical research applications, such as cell imaging, molecular detection, and analysis.
Overall, 6,7-DIMETHYL-2(1H)-QUINOXALINONE holds promise in both the pharmaceutical and research fields, with its wide range of potential applications.

InChI:InChI=1/C10H10N2O/c1-6-3-8-9(4-7(6)2)12-10(13)5-11-8/h3-5H,1-2H3,(H,12,13)

Upstream product

• 105029-06-9 6,7-dimethyl-1,2,3,4-tetrahydroquinoxalin-2-one 
• 915944-24-0 methyl 4-fluoro-2-methyl-5-nitrobenzene 
• 6000-59-5 glyoxalic acid monohydrate 
• 3171-45-7 4,5-dimethyl-1,2-phenylenediamine 
• 924-44-7 glyoxylic acid ethyl ester 
• 6295-06-3 butyl glyoxalate 
• 922-68-9 Methyl glyoxylate 

Downstream Products

• 82019-34-9 1,6,7-trimethylquinoxalin-2(1Η)-one 
• 78751-23-2 6,7-Dimethyl-3-phenyl-1,2-dihydro-chinoxalin-2-on 
• 29067-81-0 2-chloro-6,7-dimethylquinoxaline 
• 82083-10-1 6,7-Dimethyl-1-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)-2(1H)-chinoxalinon 
• 1315336-98-1 6,7-dimethyl-2-(perfluorophenyl)quinoxaline 
• 1315336-88-9 6,7-dimethylquinoxalin-2-yl 4-methylbenzenesulfonate 

Relevant academic research and scientific papers

A bis(η5-cyclopentadienyl)cobalt complex of a bis-dithiolene: A chemical analogue of the metal centres of the DMSO reductase family of molybdenum and tungsten enzymes, in particular ferredoxin aldehyde oxidoreductase

The synthesis is described of a bis-ene-1,2-dithiolate pro-ligand, designed to model the stereochemical situation in the cofactor of the tungsten enzyme ferredoxin aldehyde oxidoreductase from Pyrococcus furiosus. Each masked ene-1,2-dithiolate unit is mounted on a pyrano[2,3-b]tetrahydroquinoxaline tricycle, comparable to the pyrano[2,3-g]tetrahydropteridines found in all molybdoenzymes and tungsten analogues. Hydrolytic release of the bis-ligand was confirmed by its entrapment as a double (η5-C5H 5)Co complex.

Electro-reductive C-H cyanoalkylation of quinoxalin-2(1H)-ones

Herein, we report a practical electro-reductive protocol for the direct C–H cyanoalkylation of quinoxalin-2(1H)-ones via iminyl radical-mediated ring opening. These mild reactions proceed under metal-, reductant-, and reagent-free conditions to provide synthetically useful cyanoalkylated quinoxalin-2(1H)-ones.

Copper-Catalyzed Divergent C-H Functionalization Reaction of Quinoxalin-2(1H)-ones and Alkynes Controlled by N1-Substituents for the Synthesis of (Z)-Enaminones and Furo[2,3-b]quinoxalines

With control by N1-substituents, the switchable divergent C-H functionalization reaction of quinoxalin-2(1H)-ones is achieved for the synthesis of (Z)-enaminones and furo[2,3-b]quinoxalines using the combination of a copper catalyst and an oxidant. This new protocol features mild reaction conditions, readily available materials, and a broad substrate scope. Gram-scale and mechanistic studies were also investigated. Furthermore, the desired products exhibited excellent antitumor activity against A549, HepG-2, MCF-7, and HeLa cells, which were tested by MTT assay.

Electro-oxidative C-H alkylation of quinoxalin-2(1: H)-ones with organoboron compounds

Radical cleavage of C-B bonds to accomplish C-H functionalization is synthetically appealing but practically challenging. We report herein a mild electro-oxidative method for efficient C-H alkylation of quinoxalin-2(1H)-ones by means of radical addition reactions of alkyl boronic acids and esters and alkyl trifluoroborates to afford C-C coupled products. This journal is

Electro-oxidative C-H azolation of quinoxalin-2(1H)-ones

We have developed a practical, general protocol for direct C-H azolation reactions of quinoxalin-2(1H)-ones by electro-oxidative cross-coupling. These mild reactions proceed under metal-, oxidant-, and reagent-free conditions to provide synthetically useful azolated quinoxalin-2(1H)-ones. Furthermore, the reactions can be carried out with a pencil lead as an electrode and a 3 V battery as a power source, revealing the remarkable flexibility of this protocol.

Electrochemical chlorination and bromination of electron-deficient C[sbnd]H bonds in quinones, coumarins, quinoxalines and 1,3-diketones

The electrochemistry-promoted chlorination and bromination of electron-deficient C[sbnd]H bonds was developed, using quinones, coumarins, quinoxalines and 1,3-diketones. This protocol features readily available and safe halogen sources (hydrochloric acid and KBr), high site-selectivity and mild reaction conditions. It could provide an efficient access to a series of chlorinated and brominated quinones, coumarins, quinoxalines and 1,3-diketones.

Synthesis of (E)-Quinoxalinone Oximes through a Multicomponent Reaction under Mild Conditions

Herein, a novel method for the gram-scale synthesis of (E)-quinoxalinone oximes through a multicomponent reaction under mild conditions is described. Such a transformation was performed under transition-metal-free conditions, affording (E)-oximes in a moderate-to-good yield through recrystallization. Our methodology demonstrates a successful combination of a Mannich-type reaction and radical coupling, providing a green and practical approach for the synthesis of potentially bioactive quinoxalinone-containing molecules.

K2S2O8-catalyzed highly regioselective amidoalkylation of diverse N-heteroaromatics in water under visible light irradiation

A K2S2O8-catalyzed versatile C(sp2)-C(sp3) bond formation with N-heteroaromatics and γ-lactams/amides was developed. Quinoxalin-2(1H)-one, quinoline, isoquinoline, phthalazine, and benzothiazole reacted with γ-lactams/amides to give the corresponding C(sp2)-H amidoalkylation products in moderate to good yields with high regioselectivity. This visible-light-induced photocatalyst-free reaction was conducted in H2O at ambient temperature, which comply with the principles of "green chemistry". The new K2S2O8 catalytic mechanism was investigated with control experiments.

Visible-Light-Promoted Switchable Synthesis of C-3-Functionalized Quinoxalin-2(1H)-ones

A visible-light-promoted synthesis of quinoxalin-2(1H)-ones has been developed using 9-mesityl-10-methylacridinium perchlorate as an organo-photocatalyst. The atmosphere-controlled method (Ar/air) enabled the selective synthesis of hydroxyl- and acyl-containing quinoxalin-2(1H)-ones under mild reaction conditions without the use of any metal catalysts or toxic reagents. A fluorescent labelling experiment showed that hydroxyl-containing quinoxalin-2(1H)-ones may have utility in various biological applications as potent fluorophores. (Figure presented.).

PIDA-induced oxidative C–N bond coupling of quinoxalinones and azoles

A metal-free promoted direct oxidative C–N bond coupling of quinoxalinones and azoles for the rapid and effective synthesis of potent pharmaceutical important 3-(azol-1-yl)quinoxalin-2-one has been developed. Employing PIDA as the easily available mediator, the desired coupling products were isolated in moderate to excellent yields with a good substrate scope under operational simplicity and mild reaction conditions. Preliminary mechanistic studies suggested that a radical process is likely to be involved in the reaction.