63536-46-9

Usage

Type of compound

Heterocyclic compound

Structure

Contains a quinoxalinone ring with an ethyl substituent

Usage

Intermediate in the synthesis of various pharmaceuticals and organic compounds

Usage

Building block in the production of other chemical compounds (e.g. pesticides and dyes)

Potential

Biological activities

Applications

Medicinal chemistry and drug discovery

Note

Specific properties and uses may vary depending on the context and the specific research or industrial application.

Upstream product

• 1196-57-2 quinoxalin-2⁽¹⁾-one 
• 75-03-6 ethyl iodide 
• 1196-57-2 2-hydroxyquinoxaline 
• 74-96-4 ethyl bromide 
• 14003-34-0 3-methyl-2-oxo-1,2-dihydroquinoxaline 
• 75-00-3 chloroethane 
• 59564-59-9 1,2,3,4-tetrahydroquinoxalin-2-one 
• 5428-05-7 n-(2-nitrophenyl)glycine ethyl ester 
• 1493-27-2 ortho-nitrofluorobenzene 
• 95-54-5 1,2-diamino-benzene 
• 64-17-5 ethanol 
• 36818-07-2 ethyl 3-oxo-4H-quinoxaline-2-carboxylate 

Downstream Products

• 73148-14-8 1-ethyl-3-methylquinoxalin-2(1H)-one 
• 586348-21-2 ataquimast 
• 1186527-86-5 3-(4-chlorophenyl)-1-ethylquinoxalin-2(1H)-one 
• 88392-55-6 1-ethyl-3-phenylquinoxalin-2(1H)-one 

Relevant academic research and scientific papers

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.

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.

Rapid alkenylation of quinoxalin-2(1H)-ones enabled by the sequential Mannich-type reaction and solar photocatalysis

Herein, a rapid alkenylation of quinoxalin-2(1H)-ones enabled by a combination of Mannich-type reaction and solar photocatalysis is demonstrated. A wide range of functional groups are compatible, affording the corresponding products in moderate-to-good yields. Control experiments illustrate that the in situ generated 1O2 plays a central role in this reaction. This green and efficient strategy provides a practical solution for the synthesis of potentially bioactive compounds that containing a 3,4-dihydroquinoxalin-2(1H)-one structure.

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.

Metal-Free Direct Oxidative C?N Bond Coupling of Quinoxalin-2(1H)-ones with Azoles under Mild Conditions

Direct C3?H amination of quinoxalin-2(1H)-ones with azoles under mild conditions promoted by PIFA has been achieved in good yield in a very fast manner. Mechanistic study revealed that the reaction proceeds through a radical process. In addition, this method could be applied to gram-scale reaction.

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.

N, N, N', N'-Tetramethylethylenediamine-Enabled Photoredox-Catalyzed C-H Methylation of N-Heteroarenes

Aiming at the valuable methylation process, readily available and inexpensive N,N,N′,N′-tetramethylethylenediamine (TMEDA) was first identified as a new methyl source in photoredox-catalyzed transformation in this work. By virtue of this simple methylating reagent, a facile and practical protocol for the direct C-H methylation of N-heteroarenes was developed, featuring mild reaction conditions, broad substrate scope, and scalability. Mechanistic studies disclosed that a sequential photoredox, base-assisted proton shift, fragmentation, and tautomerization process was essentially involved.

Method for preparing quinoxaline-2-ketone derivative through controllable catalysis

The invention relates to a method for preparing a quinoxaline-2-ketone derivative through controllable catalysis. The method comprises the following steps: adding a Selectfluor reagent into an organic solvent, carrying out ultrasonic dissolution, respectively adding a quinoxaline-2-ketone compound, an alcohol and an additive into the organic solvent, carrying out a stirring reaction at room temperature under the irradiation of a light source, tracking by TLC until the raw material quinoxaline-2-ketone compound is completely reacted, then ending the reaction, and carrying out post-treatment and column chromatography separation and purification to obtain the 3-alkoxy quinoxaline-2-ketone derivative or the 3-hydroxyalkyl quinoxaline-2-ketone derivative. Clean visible light is used as reaction energy, the preparation process is simple and efficient, operation is convenient, conditions are mild, environment friendliness is achieved, the substrate application range is wide, and the method is suitable for large-scale industrial production.

Method for catalytically preparing 3-sulfur substituted quinoxalinone derivative

The invention relates to a method for catalytically preparing a 3-sulfur substituted quinoxalinone derivative. The method comprises the following steps of: firstly preparing a 3-(thiophenyl) quinoxaline-2 (1H)-ketone derivative, then adding the 3-(thiophenyl) quinoxaline-2 (1H)-ketone derivative, disulfide, an oxidizing agent and a catalyst into a reaction container, adding a solvent, reacting under the light irradiation of a blue lamp, and after the reaction is completed, filtering, extracting, concentrating, separating and purifying to obtain the 3-sulfur substituted quinoxalinone derivative. According to the invention, the problem that a traditional catalyst needs high-temperature reaction is solved, disulfide is used as a raw material, the problem that foul thiophenol and thiol substances are used as raw materials traditionally is solved, and a green and efficient synthesis method is used to promote industrialization of a reaction system; and meanwhile, quinoxalinone compounds with different substituent groups are also efficiently expanded.

Eosin Y as a direct hydrogen-atom transfer photocatalyst for the C3-H acylation of quinoxalin-2(1H)-ones

Visible light promoted eosin Y catalyzed selective C3-H acylation of quinoxalin-2(1H)-ones has been developed in a green and sustainable manner. In contrast to the conventional anionic eosin Y-based photoredox process, neutral eosin Y acts as the actual c