59489-30-4

Usage

Uses

Used in Pharmaceutical Synthesis:
7-Chloro-2-quinoxalinone is used as a building block for the synthesis of various pharmaceuticals. Its unique structure and reactivity make it a valuable component in the development of new drugs with potential therapeutic applications.
Used in Agrochemical Production:
In the agrochemical industry, 7-Chloro-2-quinoxalinone is utilized as a key intermediate in the synthesis of pesticides and other agrochemicals. Its incorporation into these products can enhance their effectiveness in controlling pests and diseases in agriculture.
Used in Organic Chemistry Reactions:
7-Chloro-2-quinoxalinone is employed as a reagent in organic chemistry, particularly in the production of heterocyclic compounds. Its ability to participate in various chemical reactions contributes to the synthesis of complex organic molecules with diverse applications.
Used in Anticancer Research:
7-Chloro-2-quinoxalinone has been found to exhibit potential anticancer properties. It is used as a compound of interest in cancer research, with the aim of developing new therapeutic agents that can target and inhibit the growth of cancer cells.
Used in Antibacterial Applications:
Due to its demonstrated antibacterial properties, 7-Chloro-2-quinoxalinone is used in the study and development of new antimicrobial agents. Its potential to combat bacterial infections makes it a valuable asset in the ongoing fight against antibiotic-resistant bacteria.

InChI:InChI=1/C8H5ClN2O/c9-5-1-2-6-7(3-5)11-8(12)4-10-6/h1-4H,(H,11,12)

Upstream product

• 66367-05-3 6-chloro-3,4-dihydroquinoxalin-2(1H)-one 
• 111697-44-0 1-hydroxy-7-chloro-2(1H)-quinoxalinone 
• 6639-80-1 6-chloroquinoxaline 1,4-dioxide 
• 66367-04-2 N-4-chloro-2-nitrophenylglycine 
• 89-63-4 4-Chloro-2-nitroaniline 
• 924-44-7 glyoxylic acid ethyl ester 
• 95-83-0 4-Chloro-1,2-phenylenediamine 

Downstream Products

• 59489-31-5 2,7-dichloroquinoxaline 
• 847900-53-2 7-chloro-5-(4-methoxybenzyl)imidazo[1,5-a]quinoxalin-4(5H)-one 
• 847900-56-5 2-[4-(7-chloro-imidazo[1,5-a]quinoxalin-4-yloxy)-phenoxy]-propionic acid methyl ester 

Relevant academic research and scientific papers

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

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.

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.).

Electrochemically C-H/S-H Oxidative Cross-Coupling between Quinoxalin-2(1 H)-ones and Thiols for the Synthesis of 3-Thioquinoxalinones

An electrochemical method for the C(sp2)-H thioetherification of quinoxalin-2(1H)-ones with primary, secondary, and tertiary thiols has been reported. Various quinoxalin-2(1H)-ones underwent this thioetherification smoothly under metal- A nd chemical oxidant-free conditions, affording 3-alkylthiol-substituted quinoxalin-2(1H)-ones in moderate to good yields.

Visible-light induced phosphonation of quinoxalines and quinoxalin-2(1H)-ones under aerobic metal-free conditions

Phosphonation of quinoxalines and quinoxalin-2(1H)-ones utilizing aerobic oxygen as green oxidant under visible light conditions at room temperature has been described. Both quinoxalines and quinoxalin-2(1H)-ones are compatible with alkyl or aryl phosphonates and provided good yields of products through regioselective C-P bond formation under base/ligand-free conditions. Competitive experiments showed quinoxalin-2(1H)-ones are more reactive than quinoxalines under the present conditions, and the control experiments revealed the present transformation proceeds through a radical mechanism.

(2-quinoxalinyloxy) phenoxypropanoic acids and related derivatives as anticancer agents

This invention relates to (2-quinoxalinyloxy)phenoxypropanoic acids, related derivatives thereof, enantiomeric and diastereomeric forms thereof, mixtures of enantiomeric diastereomeric forms thereof, and pharmaceutically acceptable salt forms thereof, pharmaceutical compositions containing them, processes for their preparation, and methods of using them to treat cancer, particularly solid tumors, in mammals.

Quinoxaline Derivatives. XII. The Reactions of Quinoxaline 1,4-Dioxides with Acetic Anhydride

Quinoxaline 1,4-dioxide (XIIIa) with acetic anhydride gave 1-acetoxy-2(1H)-quinoxalinone (XIVa) which was prone to facile hydrolysis to yield 1-hydroxy-2(1H)-quinoxalinone (XVa).Both XIVa and XVa were isolated from the reaction mixture.On prolonged heating with acetic anhydride, XIIIa, XIVa and XVa were converted slowly to the same end product, 2,3(1H,4H)-quinoxalinedione (XXa). 6-Ethoxy- (XIIIb), 6-methoxy- (XIIIc), and 6-methylquinoxaline 1,4-dioxide (XIIId) behaved similarly, except that the attack of the reagent took place exclusively on N-oxide para to the electron-donating substituents, and none of the other expected isomeric compounds XVIIb-d were isolated.Whereas 6-chloroqinoxaline 1,4-dioxide (XIIIe) bearing an electron-attracting chloro substituent on the benzene ring gave exclusively the other isomers XVIIe, XVIIIe, and XXe.A mechanism for this novel rearrangement is proposed and discussed.