71896-99-6

Usage

Uses

Used in Pharmaceutical Research:
6-NITRO-2-PHENYLQUINOXALINE is used as a research compound for exploring its potential biological and pharmacological activities. Its unique structure allows scientists to investigate its interactions with biological targets and its potential use in the development of new drugs.
Used in Organic Synthesis:
In the field of organic synthesis, 6-NITRO-2-PHENYLQUINOXALINE is used as a building block or intermediate in the synthesis of more complex organic molecules. Its presence of a nitro group and phenyl group makes it a versatile component for creating a variety of chemical compounds.
Used in Chemical Reaction Studies:
6-NITRO-2-PHENYLQUINOXALINE is utilized as a model compound for studying various chemical reactions. Its unique properties allow researchers to gain insights into reaction mechanisms and develop new synthetic methodologies.
Used in Drug Development:
Due to its potential biological and pharmacological activities, 6-NITRO-2-PHENYLQUINOXALINE is used in drug development as a candidate molecule. It may be further modified or used as a template to design new drugs with specific therapeutic effects.

InChI:InChI=1/C14H9N3O2/c18-17(19)11-6-7-12-13(8-11)15-9-14(16-12)10-4-2-1-3-5-10/h1-9H

Upstream product

• 64-04-0 phenethylamine 
• 99-56-9 4-Nitrophenylene-1,2-diamine 
• 536-74-3 phenylacetylene 
• 100-42-5 styrene 
• 100-41-4 ethylbenzene 
• 1074-12-0 phenylglyoxal hydrate 
• 70-11-1 α-bromoacetophenone 
• 2813-22-1 2-methanesulfinyl-1-phenyl-ethanone 
• 79531-98-9 dimethyl phenacyl sulfonium iodide 
• 52922-65-3 ω-(Methylthio)-ω-(methylsulfinyl)acetophenone 

Downstream Products

• 131706-07-5 N-(4-Oxy-2-phenyl-quinoxalin-6-yl)-acetamide 
• 77093-91-5 6-nitro-2-phenylquinoxaline 4-oxide 
• 131706-02-0 6-acetylamino-2-phenylquinoxaline 

Relevant academic research and scientific papers

Visible light promoted tandem dehydrogenation-deaminative cyclocondensation under aerobic conditions for the synthesis of 2-aryl benzimidazoles/quinoxalines fromortho-phenylenediamines and arylmethyl/ethyl amines

Visible light promoted domino synthesis of 2-aryl benzimidazoles is reported through the reaction ofortho-phenylenediamines and arylmethyl amines under aerobic conditions. The methodology has wide substrate scope and tolerates a wide range of functional groups affording the products in high yields. The use of arylethyl amines instead of arylmethyl amines gives 2-aryl quinoxalines.

Thiazolo[5,4-f]quinoxalines, Oxazolo[5,4-f]quinoxalines and Pyrazino[b,e]isatins: Synthesis from 6-Aminoquinoxalines and Properties

The regioselective iodination of different 2-mono-, 3-mono- and 2,3-disubstituted 6-aminoquinoxalines, which takes place at their 5-position, was rationalized on the basis of Hückel theory calculations. Oxazolo- and thiazolo[5,4-f]quinoxaline analogues of

Organocatalytic Green Approach Towards the Fabrication of Fused Benzo N,N-containing Heterocycles Facilitated by Ultrasonic Irradiation

The development of a metal-free protocol for transformations in organic synthesis offers a significant potential environmental benefit. This article reports the exploration of meglumine, a nontoxic and biodegradable amino sugar, as an organocatalyst for the synthesis of biologically active 1H-dibenzo[b,e][1,4]diazepin-1-ones, highly regioselective benzimidazole derivatives and derivatives of quinoxalines. Operational simplicity, mild reaction conditions, shorter reaction times, and use of green solvents are the highlights of this protocol. The advantage of ultrasonic irradiation has been significantly explored for the synthesis of the aforesaid compounds. Furthermore, the multifaceted use of o-phenylenediamine has also been accentuated in the study.

Nano Copper(0)-Stabilized on Alumina: Efficient and Recyclable Heterogeneous Catalyst for Chemoselective Synthesis of 1,2-Disubstituted Benzimidazoles and Quinoxalines in Aqueous Medium

Abstract: The present communication elicits the use of copper nanoparticles on aluminium oxide derived from Cu–Al hydrotalcite as a heterogeneous catalyst in the green and operationally simple approach for the synthesis of selective 1,2-disubstituted benzimidazoles and quinoxaline. Wide ranges of substituted o-phenylenediamines and aldehydes or α-bromo ketones were used to achieve the desired products using water as the reaction medium. The recoverability and reusability of the catalyst are the significant features in this eco-friendly green protocol. Graphical Abstract: A simple and efficient process for the synthesis of benzimidazoles and quinoxaline in presence of Cu(0)/Al2O3 catalyst at room temperature is described.

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.

Metal free synthesis of quinoxalines from alkynes via a cascade process using TsNBr2

A metal free protocol for the synthesis of quinoxalines from alkynes has been developed. The reaction was carried out by treating alkynes with TsNBr2in presence of O-phenylenediamines in a mixture of acetonitrile and water (9:1). This one-pot reaction proceeds via an oxidative transformation of alkynes to α,α-dibromoketones in presence of TsNBr2and eventually to quinoxalines in presence of 1,2-diamines in a cascade process.

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.).

New 6-Aminoquinoxaline Derivatives with Neuroprotective Effect on Dopaminergic Neurons in Cellular and Animal Parkinson Disease Models

Parkinson's disease (PD) is a neurodegenerative disorder of aging characterized by motor symptoms that result from the loss of midbrain dopamine neurons and the disruption of dopamine-mediated neurotransmission. There is currently no curative treatment for this disorder. To discover druggable neuroprotective compounds for dopamine neurons, we have designed and synthesized a second-generation of quinoxaline-derived molecules based on structure-activity relationship studies, which led previously to the discovery of our first neuroprotective brain penetrant hit compound MPAQ (5c). Neuroprotection assessment in PD cellular models of our newly synthesized quinoxaline-derived compounds has led to the selection of a better hit compound, PAQ (4c). Extensive in vitro characterization of 4c showed that its neuroprotective action is partially attributable to the activation of reticulum endoplasmic ryanodine receptor channels. Most interestingly, 4c was able to attenuate neurodegeneration in a mouse model of PD, making this compound an interesting drug candidate for the treatment of this disorder.

Catalyst-free synthesis of quinoxalines

Quinoxalines are a class of important heterocycles, so to explore a facile and practical new synthetic method is always demanded. We have developed a new catalyst-free domino synthesis of quinoxalines from phenacyl halides and 1,2-diaminoarenes. Phenacyl

I2 catalyzed tandem protocol for synthesis of quinoxalines via sp3, sp2 and sp C-H functionalization

One-pot, atom-economic synthesis of quinoxalines has been achieved through generation of arylglyoxal from easily available ethylarenes, ethylenearenes and ethynearenes, and subsequent condensation with o-phenylenediamines. Catalytic I2 with TBHP as an oxidant in DMSO is the system of choice for this domino reaction involving C-H functionalization/oxidative cyclization. This metal-free, mechanistically distinct and functional group tolerant tandem approach could be a powerful complement to traditional approaches for the synthesis of quinoxalines. This journal is