6639-87-8

Usage

Uses

Used in Pharmaceutical Industry:
6-NITROQUINOXALINE is used as a key intermediate in the synthesis of pharmaceuticals for its ability to contribute to the development of new drugs. Its chemical properties allow it to be a building block in the creation of various medicinal compounds, enhancing the range of treatments available for different health conditions.
Used in Agrochemical Industry:
In the agrochemical sector, 6-NITROQUINOXALINE is utilized as an intermediate in the production of agrochemicals, specifically pesticides and other crop protection agents. Its role in these applications is to help develop more effective and targeted solutions for agricultural challenges, ensuring crop yield and quality.
Used in Dye and Pigment Production:
6-NITROQUINOXALINE is employed as a starting material in the manufacturing of dyes and pigments, where its chemical structure contributes to the color and stability of the final products. This application is crucial in various industries, including textiles, plastics, and printing inks, for creating vibrant and long-lasting colors.
Used in Environmental Management:
Given its potential hazards, 6-NITROQUINOXALINE is also used in the development of methods for its safe handling and disposal, ensuring minimal environmental impact. This includes the creation of guidelines and technologies for the safe management of this chemical compound throughout its lifecycle, from production to disposal.

InChI:InChI=1/C8H5N3O2/c12-11(13)8-2-1-6-4-9-10-5-7(6)3-8/h1-5H

Upstream product

• 91-19-0 2,3-diethynylquinoxaline 
• 75-07-0 acetaldehyde 
• 99-56-9 4-Nitrophenylene-1,2-diamine 
• 107-21-1 ethylene glycol 
• 3476-89-9 1,2,3,4-tetrahydroquinoxaline 
• 131543-46-9 Glyoxal 
• 141090-51-9 6-nitro-1,4-dinitroso-1,2,3,4-tetrahydroquinoxaline 
• 517-21-5 glyoxal sodium bisulfite 

Downstream Products

• 2379-56-8 6-nitro-1,2,3,4-tetrahydroquinoxaline-2,3-dione 
• 6298-37-9 6-aminoquinoxaline 
• 41959-35-7 6-nitro-1,2,3,4-tetrahydroquinoxaline 
• 231-23-2 pyrazino[2,3-f]quinoxaline 
• 1417556-87-6 (S)-2-(2-(3-cyclopropyl-4-(2-hydroxyethyl)-5-methyl-1H-pyrazol-1-yl)acetamido)-N-methyl-3-phenyl-N-(quinoxalin-6-yl)propanamide 
• 1417557-06-2 (S)-2-amino-N-methyl-3-phenyl-N-(quinoxalin-6-yl)propanamide 
• 1417557-05-1 (S)-2-(1,3-dioxoisoindolin-2-yl)-N-methyl-3-phenyl-N-(quinoxalin-6-yl)propanamide 
• 888037-23-8 N6-methylquinoxaline-5,6-diamine 
• 57436-95-0 quinoxaline-5,6-diamine 
• 100881-61-6 N-(5-nitro-quinoxalin-6-yl)-toluene-4-sulfonamide 
• 109504-68-9 N-quinoxalin-6-yl-toluene-4-sulfonamide 
• 109541-21-1 6-chloro-7-nitroquinoxaline 
• 55686-94-7 2-Chloro-7-nitroquinoxaline 
• 6272-25-9 2-Chloro-6-nitroquinoxaline 

Relevant academic research and scientific papers

Pressure Effects on the Thermal Decomposition of Nitramines, Nitrosamines, and Nitrate Esters

Solutions of nitramine and nitrate ester explosives and model compounds were thermolyzed at various hydrostatic pressures and their rates of decomposition were measured.The effects of pressure on their rates were used to infer the mechanism of their initi

Synthesis and characterization of novel fluorescent compounds derived from 1,4-diethyl-1,2,3,4-tetrahydro-6-nitroquinoxaline

(Chemical Equation Presented) 1,4-Diethyl-1,2,3,4-tetrahydro-6- nitroquinoxaline 4 was synthesized by alkylative reduction of 6-nitroquinoxaline. Catalytic reduction of 4 followed by cyclocondensation with heterocyclic malondialdehydes afforded novel 8-(heteroaryl)-1,4-diethyl-1,2,3,4- tetrahydropyrido[2,3-g]quinoxalines. The solutions of these novel compounds having 1,4-diethyl-1,2,3,4-tetrahydroquinoxaline framework as an electron releasing system showed absorption in the range of 424-426 nm in the visible region and exhibited brilliant bluish-green fluorescence. The thermogravimetric curve obtained by thermogravimetric analysis displayed that these fluorophores possess excellent thermal stability with one-step thermal decomposition.

Synthesis, biological evaluation, and in silico studies of new acetylcholinesterase inhibitors based on quinoxaline scaffold

A quinoxaline scaffold exhibits various bioactivities in pharmacotherapeutic interests. In this research, twelve quinoxaline derivatives were synthesized and evaluated as new acetyl-cholinesterase inhibitors. We found all compounds showed potent inhibitory activity against acetyl-cholinesterase (AChE) with IC50 values of 0.077 to 50.080 μM, along with promising predicted drug-likeness and blood–brain barrier (BBB) permeation. In addition, potent butyrylcholinesterase (BChE) inhibitory activity with IC50 values of 14.91 to 60.95 μM was observed in some compounds. Enzyme kinetic study revealed the most potent compound (6c) as a mixed-type AChE inhibitor. No cytotoxicity from the quinoxaline derivatives was noticed in the human neuroblastoma cell line (SHSY5Y). In silico study suggested the compounds preferred the peripheral anionic site (PAS) to the catalytic anionic site (CAS), which was different from AChE inhibitors (tacrine and galanthamine). We had proposed the molecular design guided for quinoxaline derivatives targeting the PAS site. Therefore, the quinoxaline derivatives could offer the lead for the newly developed candidate as potential acetylcholinesterase inhibitors.

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

Photochemistry of Heteroleptic 1,4,5,8-Tetraazaphenanthrene- And Bi-1,2,3-triazolyl-Containing Ruthenium(II) Complexes

Diimine metal complexes have significant relevance in the development of photodynamic therapy (PDT) and photoactivated chemotherapy (PACT) applications. In particular, complexes of the TAP ligand (1,4,5,8-tetraazaphenanthrene) are known to lead to photoinduced oxidation of DNA, while TAP- and triazole-based complexes are also known to undergo photochemical ligand release processes relevant to PACT. The photophysical and photochemical properties of heteroleptic complexes [Ru(TAP)n(btz)3-n]2+ (btz = 1,1′-dibenzyl-4,4′-bi-1,2,3-triazolyl, n = 1 (1), 2 (2)) have been explored. Upon irradiation in acetonitrile, 1 displays analogous photochemistry to that previously observed for [Ru(bpy)(btz)2]2+ (bpy = 2,2′-bipyridyl) and generates trans-[Ru(TAP)(btz)(NCMe)2]2+ (5), which has been crystallographically characterized, with the observation of the ligand-loss intermediate trans-[Ru(TAP)(κ2-btz)(κ1-btz)(NCMe)]2+ (4). Complex 2 displays more complicated photochemical behavior with not only preferential photorelease of btz to form cis-[Ru(TAP)2(NCMe)2]2+ (6) but also competitive photorelease of TAP to form 5. Free TAP is then taken up by 6 to form [Ru(TAP)3]2+ (3) with the proportion of 5 and 3 observed to progressively increase during prolonged photolysis. Data suggest a complex set of reversible photochemical ligand scrambling processes in which 2 and 3 are interconverted. Computational DFT calculations have enabled optimization of geometries of the pro-trans 3MCcis states with repelled btz or TAP ligands crucial for the formation of 5 from 1 and 2, respectively, lending weight to recent evidence that such 3MCcis states play an important mechanistic role in the rich photoreactivity of Ru(II) diimine complexes.

Metal-free regioselective nitration of quinoxalin-2(1H)-ones withtert-butyl nitrite

A metal-free coupling of quinoxalin-2(1H)-ones withtert-butyl nitrite has been developed. Distinctly from the previous functionalization of quinoxalin-2(1H)-ones, this nitration reaction took place selectively at the C7 or C5 position of the phenyl ring, affording a series of 7-nitro and 5-nitro quinoxalin-2(1H)-ones in moderate to good yields. Preliminary mechanistic studies revealed that the reaction may involve a radical process.

Compound used as EGFR kinase inhibitor and application thereof

The invention relates to a compound used as an EGFR kinase inhibitor and application thereof, the compound has a structure as shown in a formula I, and the compound can be used for adjusting EGFR kinase activity or treating related diseases, especially non-small cell lung cancer.

ARYL-PHOSPHORUS-OXYGEN COMPOUND AS EGFR KINASE INHIBITOR

Disclosed is a class of new aryl-phosphorus-oxygen compounds as shown in formula (I) as EGFR kinase inhibitors, and pharmaceutically acceptable salts thereof.

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.

Meta C-H Arylation of Electron-Rich Arenes: Reversing the Conventional Site Selectivity

Controlling site selectivity of C-H activation without using a directing group remains a significant challenge. While Pd(II) catalysts modulated by a mutually repulsive pyridine-type ligand have been shown to favor the relatively electron-rich carbon centers of arenes, reversing the selectivity to favor palladation at the relatively electron-deficient positions has not been possible. Herein we report the first catalytic system that effectively performs meta C-H arylation of a variety of alkoxy aromatics including 2,3-dihydrobenzofuran and chromane with exclusive meta site selectivity, thus reversing the conventional site selectivity governed by native electronic effects. The identification of an effective ligand and modified norbornene (NBE-CO2Me), as well as taking advantage of the statistics, are essential for achieving the exclusive meta selectivity.