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Usage

Uses

Used in Pharmaceutical Synthesis:
2-Hydroxy-6,7-dichloroquinoxaline is used as a key intermediate in the synthesis of pharmaceutical drugs due to its unique chemical properties and reactivity. It contributes to the development of new therapeutic agents with potential applications in various medical fields.
Used in Agrochemical Synthesis:
In the agrochemical industry, 2-Hydroxy-6,7-dichloroquinoxaline serves as a crucial building block for the synthesis of agrochemicals. Its incorporation into these compounds can enhance their effectiveness in pest control and crop protection.
Used as an Antimicrobial Agent:
2-Hydroxy-6,7-dichloroquinoxaline is utilized as an antimicrobial agent for its potential to combat various microorganisms. Its ability to inhibit microbial growth makes it a promising candidate for applications in healthcare and sanitation.
Used as an Antiviral Agent:
2-HYDROXY-6,7-DICHLOROQUINOXALINE is also explored for its antiviral properties, making it a potential candidate for the development of antiviral drugs. Its ability to interfere with viral replication and infection processes can contribute to the treatment and prevention of viral diseases.
Used as an Anticancer Agent:
2-Hydroxy-6,7-dichloroquinoxaline has been studied for its potential as an anticancer agent, with research focusing on its ability to target and inhibit the growth of cancer cells. Its incorporation into cancer therapeutics could lead to the development of novel treatments for various types of cancer.
Used as a Corrosion Inhibitor:
In the field of materials science, 2-Hydroxy-6,7-dichloroquinoxaline is investigated for its potential use as a corrosion inhibitor. Its ability to protect metals from corrosion can be applied in various industries, including automotive, aerospace, and construction, to enhance the durability and longevity of metal components.
Used as a Precursor in Organic Synthesis:
2-HYDROXY-6,7-DICHLOROQUINOXALINE also serves as a precursor in the synthesis of various organic compounds. Its unique structure and reactivity enable the creation of a wide range of organic molecules with diverse applications in chemistry, materials science, and pharmaceuticals.

InChI:InChI=1/C8H4Cl2N2O/c9-4-1-6-7(2-5(4)10)12-8(13)3-11-6/h1-3H,(H,12,13)

Upstream product

• 75294-00-7 6,7-Dichloro-3,4-dihydro-3-oxo-2-quinoxaline carboxylic acid 
• 5348-42-5 4,5-Dichloro-1,2-phenylenediamine 
• 298-12-4 Glyoxilic acid 
• 6295-06-3 butyl glyoxalate 
• 90793-48-9 N-(4,5-Dichlor-2-nitro-phenyl)-glycin-ethylester 
• 2339-78-8 1,2-dichloro-4-fluoro-5-nitrobenzene 
• 60578-70-3 6,7-dichloro-3-oxo-3,4-dihydro-quinoxaline-2-carboxylic acid ethyl ester 
• 6306-39-4 1,2-dichloro-4,5-dinitrobenzene 
• 924-44-7 glyoxylic acid ethyl ester 
• 153505-40-9 6,7-Dichloro-3,4-dihydroquinoxalin-2(1H)-one 

Downstream Products

• 41213-31-4 2,6,7-trichloro-quinoxaline 
• 50616-86-9 6,7-dichloro-1-methyl-3-phenylquinoxalin-2(1H)-one 
• 1503-80-6 6,7-dichloro-3-phenylquinoxalin-2(1H)-one 
• 82083-11-2 6,7-Dichlor-1-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)-2(1H)-chinoxalinon 
• 143007-04-9 1-Phenyl-7,8-dichloro-1,2,4-triazolo[4,3-a]quinoxalin-4(5H)-one 
• 145369-80-8 1-Phenyl-7,8-dichloro-1,2,4-triazolo [4,3-a]quinoxaline 

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.

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.

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.

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.

Direct functionalization of quinoxalin-2(1H)-one with alkanes: C(sp2)-H/C(sp3)-H cross coupling in transition metal-free mode

Considering the significance of pharmaceutically important heterocycles, efficient and highly versatile protocols for the functionalization of diverse heterocycles with easily accessible feedstock are crucial. Here, we have reported selective alkylation of quinoxalin-2(1H)-one with a broad class of hydrocarbons having different C(sp3)-H bonds with varying bond strengths using di-tert-butyl peroxide (DTBP) as an alkoxyl radical mediator for hydrogen atom transfer (HAT). This dehydrogenative coupling approach utilizes feedstock chemicals such as cycloalkanes, cyclic ethers and alkyl arenes as coupling partners. This protocol exhibits good functional group compatibility and selectivity regarding both heterocycles and unactivated alkanes. Moreover, this methodology allows functionalization of relatively strong C-H bonds of adamantane and exclusive selectivity towards 3° C(sp3)-H bonds is observed. We also illustrate the applicability of this C(sp2)-H/C(sp3)-H cross-coupling for practical access to bioactive pharmaceuticals.

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.

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.