17635-24-4

Usage

Uses

Used in Pharmaceutical Industry:
Quinoxaline, 6-fluoro-2,3-dimethyl(8CI) is used as a pharmaceutical compound for its potential antimicrobial, antiviral, antitumor, and antibacterial properties. Its unique structure and functional groups contribute to its diverse pharmacological activities, making it a valuable candidate for the development of new drugs and therapies.
Used in Medicinal Chemistry:
In the field of medicinal chemistry, Quinoxaline, 6-fluoro-2,3-dimethyl(8CI) is utilized for its potential to be further investigated and optimized for specific therapeutic applications. Its unique structure allows for modifications and the development of new analogs with improved pharmacological properties, enhancing its potential as a lead compound in drug discovery and development processes.

Upstream product

• 367-31-7 4-fluoro-1,2-phenylenediamine 
• 431-03-8 dimethylglyoxal 
• 364-78-3 2-nitro-4-fluoroaniline 
• 513-85-9 2.3-butanediol 

Downstream Products

• 941283-06-3 2,3-dimethyl-6-(1-pyrrolidinyl)quinoxaline 
• 941283-07-4 2,3-dimethyl-6-(1-piperidinyl)quinoxaline 
• 941283-14-3 2,3-dimethyl-6-(1H-imidazol-1-yl)quinoxaline 

Relevant academic research and scientific papers

In water organic synthesis: Introducing itaconic acid as a recyclable acidic promoter for efficient and scalable synthesis of quinoxaline derivatives at room temperature

Substituted quinoxaline derivatives are traditionally synthesized by co-condensation of various starting materials. Herein, we describe a novel environmentally benign in water synthetic route for the synthesis of structurally and electronically diverse ninety quinoxalines with readily available substituted o-phenylenediamine and 1,2-diketones using cheap and biodegradable itaconic acid as a mild acid promotor in 1 hours. The reaction is performed at room temperature, which proceeds through cyclo-condensation reaction followed by obtaining the aforesaid nitrogen-containing heterocyclic adducts without performing the column chromatography up to 96% total yields. The simplicity, high efficiency, and reusable of the catalyst merits this reaction condition as “green synthesis” which enables it to be useful in synthetic transformations upto gram scale level.

NaOH-Mediated Direct Synthesis of Quinoxalines from o-Nitroanilines and Alcohols via a Hydrogen-Transfer Strategy

A NaOH-mediated sustainable synthesis of functionalized quinoxalines is disclosed via redox condensation of o-nitroamines with diols and α-hydroxy ketones. Under optimized conditions, various o-nitroamines and alcohols are well tolerated to generate the desired products in 44-99% yields without transition metals and external redox additives.

Aqueous hydrofluoric acid catalyzed facile synthesis of 2,3,6-substituted quinoxalines

A versatile synthetic route for the preparation of 2,3,6-trisubstituted quinoxalines in excellent yield is developed from θ-diamines and 1,2-dicarbonyl compounds in which aqueous hydrofluoric acid was employed as the medium and catalyst. Other salient features of this protocol include milder conditions, absence of coupling agents, and easy workup procedures.

Efficient synthesis of quinoxalines from 2-nitroanilines and vicinal diols via a rutheniumcatalyzed hydrogen transfer strategy

Via a ruthenium-catalyzed hydrogen transfer strategy, we have demonstrated a one-pot method for efficient synthesis of quinoxalines from 2-nitroanilines and biomass-derived vicinal diols for the first time. In such a synthetic protocol, the diols and the nitro group serve as the hydrogen suppliers and acceptors, respectively. Hence, there is no need for the use of external reducing agents. Moreover, it has the advantages of operational simplicity, broad substrate scope and the use of renewable reactants, offering an important basis for accessing various quinoxaline derivatives.

One-pot synthesis of quinoxalines from reductive coupling of 2-nitroanilines and 1,2-diketones using indium

The one-pot reduction-cyclization of 2-nitroanilines and 1,2-diketones to give quinoxalines was investigated. Using indium and an appropriate acid such as acetic acid or indium(III) chloride, various quinoxaline derivatives including 2,3-dialkylquinoxalines, 2,3-diphenylquinoxalines, 2,3-di-2-thiophenylquinoxalines, 2,3-di(pyridin-2-yl)quinoxalines, and dibenzo[a,c]phenazines were synthesized in moderate to excellent yield.

Asymmetric hydrogenation of 2-and 2,3-substituted ouinoxalines with chiral cationic ruthenium diamine catalysts

The enantioselective hydrogenation of 2-alkyl- and 2-aryl-subsituted quinoxalines and 2,3-disubstituted quinoxalines was developed by using the cationic Ru(η6-cymene)(monosulfonylated diamine)(BArF) system in high yields with up to 99% ee. The counteranion was found to be critically important for the high enantioselectivity and/or diastereoselectivity.

Preparation of 6-substituted quinoxaline JSP-1 inhibitors by microwave accelerated nucleophilic substitution

A small library of 6-aminoquinoxalines has been prepared by nucleophilic substitution of 6-fluoroquinoxaline with amines and nitrogen-containing heterocycles under computer-controlled microwave irradiation. Some compounds were found to be potent inhibitors of JNK Stimulatory Phosphatase-1 (JSP-1) in an in vitro biological assay.