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Usage

Uses

Used in Pharmaceutical Development:
2-(4-nitrophenyl)quinoxaline is used as a key intermediate in the synthesis of pharmaceuticals for its unique reactivity and structural properties. It aids in the creation of complex organic molecules with potential therapeutic applications.
Used in Agrochemical Synthesis:
In the agrochemical industry, 2-(4-nitrophenyl)quinoxaline is used as a precursor in the development of new pesticides and other agrochemicals, leveraging its chemical properties to enhance the effectiveness of these products.
Used in Materials Science:
2-(4-nitrophenyl)quinoxaline is utilized as a component in the synthesis of advanced materials, such as organic semiconductors and other specialty materials, due to its distinctive structure and reactivity that contribute to the desired material properties.
Used in Organic Synthesis Research:
As a building block in organic synthesis, 2-(4-nitrophenyl)quinoxaline is used in academic and industrial research settings to explore new synthetic pathways and develop innovative compounds for various applications.

Upstream product

• 99-81-0 4-Nitrophenacyl bromide 
• 95-54-5 1,2-diamino-benzene 
• 4974-57-6 4-nitrophenylglyoxal 
• 46417-99-6 2-nitro-1-(4-nitrophenyl)-1-ethanone 
• 5021-43-2 2-phenylquinoxaline 
• 39214-83-0 3-(4-nitrophenyl)isoxazol-5(4H)-one 
• 25233-82-3 1-(4-nitrophenyl)-4-phenyl-2-butene-1,4-dione 
• 100-19-6 (4-nitrophenyl)ethanone 
• 38622-91-2 [(p-methylphenyl)sulfonylmethyl]isonitrile 
• 555-16-8 4-nitrobenzaldehdye 
• 1374568-15-6 2,2-diiodo-1-(4-nitrophenyl)ethanol 
• 64611-67-2 2-hydroxy-1-(4-nitrophenyl)ethanone 
• 1434751-60-6 2-benzoyl-4-(4-nitrophenyl)-1-phenylbut-2-ene-1,4-dione 
• 100-12-9 4-ethylnitrobenzene 

Downstream Products

• 81622-74-4 4-(quinoxalin-2-yl)aniline 
• 1252875-96-9 (S)-2-(4-nitrophenyl)-1,2,3,4-tetrahydroquinoxaline 
• 1444302-56-0 2-(2-fluoro-4-nitrophenyl)quinoxaline 
• 855933-25-4 N-acetyl-sulfanilic acid-(4-quinoxalin-2-yl-anilide) 

Relevant academic research and scientific papers

Silica supported dodecatungstophosphoric acid (DTP/SiO2): An efficient and recyclable heterogeneous catalyst for rapid synthesis of quinoxalines

A facile synthesis of quinoxalines by the cyclocondensation of substituted phenacyl bromides with o-pheneylenediamines using silica-supported dodecatungstophosphoric acid (DTP/SiO2) as a recyclable heterogeneous catalyst is unveiled in this res

Nature of the Nucleophilic Oxygenation Reagent Is Key to Acid-Free Gold-Catalyzed Conversion of Terminal and Internal Alkynes to 1,2-Dicarbonyls

2,3-Dichloropyridine N-oxide, a novel oxygen transfer reagent, allows the conductance of the gold(I)-catalyzed oxidation of alkynes to 1,2-dicarbonyls in the absence of any acid additives and under mild conditions to furnish the target species, including those derivatized by highly acid-sensitive groups. The developed strategy is effective for a wide range of alkyne substrates such as terminal- and internal alkynes, ynamides, alkynyl ethers/thioethers, and even unsubstituted acetylene (40 examples; yields up to 99%). The oxidation was successfully integrated into the trapping of reactive dicarbonyls by one-pot heterocyclization and into the synthesis of six-membered azaheterocycles. This synthetic acid-free route was also successfully applied for the total synthesis of a natural 1,2-diketone.

Iridium-Catalyzed Carbenoid Insertion of Sulfoxonium Ylides for Synthesis of Quinoxalines and β-Keto Thioethers in Water

Sulfoxonium ylides as safe carbene precursors are described for iridium-catalyzed carbene insertions and annulation, providing a facile and green approach to access a variety of quinoxaline derivatives in water. This water-mediated method also allows the preparation of β-keto thioethers under mild condition.

Green synthesis of novel quinoxaline sulfonamides with antibacterial activity

A facile and efficient method was investigated for the synthesis of different quinoxalines by the reaction of o-phenylene diamine and 2-bromoacetophenones. This procedure was carried out in ethanol under catalyst-free conditions. Several sulfonamides were synthesized from 2-(4-methoxyphenyl)-quinoxaline in two steps. At first chlorosulfonation of 2-(4-methoxyphenyl) quinoxaline was done using chlorosulfonic acid and led to 2-methoxy-5-quinoxalin-2-yl-benzenesulfonyl chloride. Then quinoxaline sulfonamides were synthesized by the reaction of quinoxaline sulfonyl chloride with different aromatic amines under solvent-free conditions. All the products were obtained in excellent yields after an easy work-up and were evaluated for antibacterial activities against Staphylococcus spp. and Escherichiacoli bacteria.

Synthesis of Indoles and Pyrroles Utilizing Iridium Carbenes Generated from Sulfoxonium Ylides

Metal carbenes can undergo a myriad of synthetic transformations. Sulfur ylides are potential safe precursors of metal carbenes. Herein, we report cascade reactions that involve carbenoids derived from sulfoxonium ylides for the efficient and regioselective synthesis of indoles and pyrroles. The tandem action of iridium and Br?nsted acid catalysts enables rapid assembly of the heterocycles from unmodified anilines or readily accessible enamines under microwave irradiation. The key mechanistic steps are the catalytic transformation of the sulfoxonium ylide into an iridium–carbene complex, followed by N?H or C?H functionalization of an aniline or enamine, respectively, and a final acid-catalyzed cyclization. The present method was successfully applied to the synthesis of the densely functionalized pyrrole subunit of atorvastatin.

Copper-catalyzed aerobic oxidative coupling of o-phenylenediamines with 2-aryl/heteroarylethylamines: direct access to construct quinoxalines

A copper-catalyzed oxidative coupling reaction of o-phenylenediamines with 2-aryl/heteroarylethylamines using molecular oxygen as an oxidant has been developed. This approach provides a practical and direct access to construct quinoxalines in excellent yields at room temperature. The reaction has a broad substrate scope and exhibits excellent functional-group tolerance. This method could be easily scaled up and applied to the synthesis of biologically active molecules bearing a quinoxaline structural scaffold.

One-Pot Protocol for the Synthesis of Imidazoles and Quinoxalines using N-Bromosuccinimide

N-bromosuccinimide (NBS)-mediated one-pot, green, efficient and practical synthesis of substituted imidazoles and quinoxalines has been achieved by the reaction of styrenes with N-arylbenzamidines and o-phenylenediamines, respectively, in a water:1,4-dioxane mixture. The reaction involves formation of an α-bromo ketone as an intermediate in the presence of NBS and water, followed by condensation with the N-arylbenzamidine and o-phenylenediamine. Use of an inexpensive NBS as a bromine source as well as an oxidant, water as a solvent and readily available starting materials makes this protocol environmentally benign and economically viable. Substituted imidazoles and quinoxalines were obtained in good to excellent yields with wide functional group compatibility. (Figure presented.).

One-step approach for the synthesis of functionalized quinoxalines mediated by T3P-DMSO or T3P: Via a tandem oxidation-condensation or condensation reaction

An easy and efficient propylphosphonic anhydride (T3P)-DMSO or T3P mediated oxidation-condensation or condensation reaction for the synthesis of quinoxalines derived from the interaction of different arrays of condensing partners with ortho-phenylene diamines (o-PDs) under simple and mild reaction conditions in one step has been reported for the first time.

Recyclable acidic br?nsted ionic liquid catalyzed synthesis of quinoxaline

The acidic ionic liquid, 1-(4-sulfonic acid) butyl-3-methylimidazolium hydrogen sulfate [MimC4SO3H]HSO4 catalyzed two-component condensation reaction of phenacyl bromide and o-phenylenediamine to afford corresponding quinoxaline derivatives. The inexpensive and non-toxic ionic liquids can be reused several times without any perceptible loss of their activities.

Synthesis of quinoxaline using silica supported phosphomolybdic acid as reusable heterogeneous catalyst

Using phosphomolybdic acid on silica as recyclable catalyst we have developed methodology for the synthesis of quinoxalines by condensation of phenacyl bromides and o-phenylene diamines in ClCH2CH2Cl at 80°C. The phosphomolybdic acid