6479-18-1

Basic information

• Product Name: 1-methylquinoxalin-2(1H)-one
• Synonyms: 1-Methylquinoxalin-2(1H)-one; 2(1H)-quinoxalinone, 1-methyl-
• CAS NO: 6479-18-1
• Molecular Formula: C₉H₈N₂O
• Molecular Weight: 160.1726
• Mol File: 6479-18-1.mol

Chemical Properties

• Boiling Point: 296.8°C at 760 mmHg
• Flash Point: 133.3°C
• Density: 1.21g/cm³
• Vapor Pressure: 0.0014mmHg at 25°C
• Refractive Index: 1.622
• CAS DataBase Reference: 1-methylquinoxalin-2(1H)-one(CAS DataBase Reference)
• NIST Chemistry Reference: 1-methylquinoxalin-2(1H)-one(6479-18-1)
• EPA Substance Registry System: 1-methylquinoxalin-2(1H)-one(6479-18-1)

Safety Data

• Hazardous Substances Data: 6479-18-1(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Research:
1-methylquinoxalin-2(1H)-one is used as a research compound for its potential anticancer, anti-inflammatory, and antimicrobial properties. Its unique structure makes it a promising candidate for the development of new drugs to treat various diseases.
Used in Organic Synthesis:
1-methylquinoxalin-2(1H)-one is used as a building block in the synthesis of various pharmaceuticals and agrochemicals, contributing to the development of novel compounds with therapeutic and agricultural applications.
Used in Drug Development:
1-methylquinoxalin-2(1H)-one is identified as a potential component in the development of new drugs, particularly for the treatment of various diseases, due to its demonstrated biological activities and versatility in chemical synthesis.

Upstream product

• 1196-57-2 quinoxalin-2⁽¹⁾-one 
• 77-78-1 dimethyl sulfate 
• 4760-34-3 N-methyl-1,2-phenylenediamine 
• 6295-06-3 butyl glyoxalate 
• 1719-57-9 Chloro(chloromethyl)dimethylsilane 
• 1196-57-2 2-hydroxyquinoxaline 
• 74-88-4 methyl iodide 
• 14003-34-0 3-methyl-2-oxo-1,2-dihydroquinoxaline 
• 74-87-3 methylene chloride 
• 59564-59-9 1,2,3,4-tetrahydroquinoxalin-2-one 
• 5428-05-7 n-(2-nitrophenyl)glycine ethyl ester 
• 1493-27-2 ortho-nitrofluorobenzene 
• 74-89-5 methylamine 
• 20934-50-3 1-methyl-1,2,3,4-tetrahydroquinoxalin-2-one 

Downstream Products

• 31595-64-9 3-Hydrazino-1-methylchinoxalin-2(1H)on 
• 2048-37-5 1-methyl-3-phenylquinoxalin-2(1H)-one (3a) 
• 25160-82-1 1-methyl-3-phenyl-3,4-dihydroquinoxalin-2(1H)-one 
• 37413-49-3 3-(2-methoxyphenyl)-1-methylquinoxalin-2(1H)-one 
• 1057224-07-3 3-(4-fluorophenyl)-1-methylquinoxalin-2(1H)-one 

Relevant articles and documents

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.

Photoinitiated Multicomponent Anti-Markovnikov Alkoxylation over Graphene Oxide

The development of graphene oxide–based heterogeneous materials with an economical and environmentally–friendly manner has the potential to facilitate many important organic transformations but proves to have few relevant reported reactions. Herein, we explore the synergistic role of catalytic systems driven by graphene oxide and visible light that form nucleophilic alkoxyl radical intermediates, which enable an anti-Markovnikov addition exclusively to the terminal alkenes, and then the produced benzyl radicals are subsequently added with N–methylquinoxalones. This photoinduced cascade radical difunctionalization of olefins offers a concise and applicable protocol for constructing alkoxyl–substituted N–methylquinoxalones.

Application of biomass-supported copper-catalyzed three-component reaction in preparation of fluorine-containing drugs

The invention relates to an application of a biomass-supported copper-catalyzed three-component reaction in preparation of a fluorine-containing drug. The indole and its derivatives and are synthesized 3 - (2 - (trifluoromethyl) - indo -3 -yl) quinoxaline -2 - ketone derivatives by one-pot synthesis by three-component one-pot method. To the invention, the heterogeneous biological substance carried copper catalyst is adopted to catalyze the reaction, and the problems that a traditional homogeneous catalyst cannot be recovered, metal residues are left and the like are solved. 3 - (2 - (Trifluoromethyl) - indo -3 -yl) quinoxaline -2 - ketone compounds with different substituents are expanded, and the biomass supported copper catalyst can be cyclically and catalytically reacted.

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.

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.

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 Radical Relay Cyclization/C-C Bond Formation of N-Allylbromodifluoroacetamides with Quinoxalin-2(1 H)-ones

A visible light-promoted radical relay of N-allylbromodifluoroacetamide with quinoxalin-2(1H)-ones was developed in which 5-exo-trig cyclization and C-C bond formation were involved. This protocol was performed under mild conditions to facilely offer a variety of hybrid molecules bearing both quinoxalin-2(1H)-one and 3,3-difluoro-γ-lactam motifs. These prepared novel skeletons would expand the accessible chemical space for structurally complex heterocycles with potential biological activities.

Direct photoexcitation of benzothiazolines: Acyl radical generation and application to access heterocycles

An acyl radical generation and functionalization strategy through direct photoexcitation of benzothiazolines has been developed. The formed acyl radical species can either be trapped by quinoxalin-2-ones to realize their C(3)-H functionalization or trigger a cascade radical cyclization with isonitriles to synthesise biologically important phenanthridines. The synthetic value of this protocol can be further illustrated by the modification of quinoxalin-2-ones, containing important natural products and drug-based complex molecules.

C?H Methylation of Iminoamido Heterocycles with Sulfur Ylides**

The direct methylation of N-heterocycles is an important transformation for the advancement of pharmaceuticals, agrochemicals, functional materials, and other chemical entities. Herein, the unprecedented C(sp2)-H methylation of iminoamido heterocycles as nucleoside base analogues is described. Notably, trimethylsulfoxonium salt was employed as a methylating agent under aqueous conditions. A wide substrate scope and excellent level of functional-group tolerance were attained. Moreover, this method can be readily applied to the site-selective methylation of azauracil nucleosides. The feasibility of gram-scale reactions and various transformations of the products highlight the synthetic potential of the developed method. Combined deuterium-labeling experiments aided the elucidation of a plausible reaction mechanism.