243-55-0

Usage

Chemical structure

A polycyclic aromatic hydrocarbon compound with a fused indene and quinoxaline ring system.

Physical state

Yellow crystalline solid.

Molecular weight

234.27 g/mol

Significance in organic chemistry

Potential use as a building block for the synthesis of more complex organic molecules.

Fluorescence properties

Exhibits interesting fluorescence properties, making it a promising candidate for use in organic light-emitting diodes (OLEDs) and other optoelectronic devices.

Biological and pharmacological activities

Studied for its potential antitumor and anti-inflammatory properties.

Upstream product

• 16214-27-0 indan-1,2-dione 
• 95-54-5 1,2-diamino-benzene 
• 1197040-29-1 phenyl isocyanate 
• 40400-15-5 2-(2-iodophenyl)acetonitrile 
• 59473-45-9 2-(chloromethyl)iodobenzene 
• 15028-10-1 indan-1,2-dione-2-oxime 
• 83-33-0 inden-1-one 
• 1775-27-5 2-bromoindanone 
• 615-13-4 2-indanone 
• 91-56-5 indole-2,3-dione 
• 579-07-7 1-Phenylpropane-1,2-dione 
• 1579-14-2 2-chloroindanone 
• 6954-91-2 11H-Indeno[1,2-b]quinoxaline-11-one 

Relevant academic research and scientific papers

Green Synthesis of Indeno[1,2-b]quinoxalines Using β-Cyclodextrin as Catalyst

An efficient, mild, and green method was developed for the synthesis of indeno[1,2b]quinoxaline derivatives via o-phenylenediamine (OPD) and 2-indanone derivatives utilizing βcyclodextrin (β-CD) as the supramolecular catalyst. The reaction can be carried out in water and in a solid state at room temperature. β-CD can also catalyze the reaction of indan-1,2-dione with OPD with a high degree of efficiency. Compared to the reported methods, this procedure is milder, simpler, and less toxic, making it an eco-friendly alternative. In addition, the β-CD can be recovered and reused without the loss of activity.

Activities of quinoxaline, nitroquinoxaline, and [1,2,4]triazolo [4,3-a]quinoxaline analogs of mmv007204 against schistosoma mansoni

The reliance on one drug, praziquantel, to treat the parasitic disease schistosomiasis in millions of people a year shows the need to further develop a pipeline of new drugs to treat this disease. Recently, an antimalarial quinoxaline derivative (MMV007204) from the Medicines for Malaria Venture (MMV) Malaria Box demonstrated promise against Schistosoma mansoni. In this study, 47 synthesized compounds containing quinoxaline moieties were first assayed against the larval stage of this parasite, newly transformed schistosomula (NTS); of these, 16 killed over 70% NTS at 10mM. Further testing against NTS and adult S. mansoni yielded three compounds with 50% inhibitory concentrations (IC50s) of#0.31mM against adult S. mansoni and selectivity indices of$8.9. Administration of these compounds as a single oral dose of 400mg/kg of body weight to S. mansoni-infected mice yielded only moderate worm burden reduction (WBR) (9.3% to 46.3%). The discrepancy between these compounds' good in vitro activities and their poor in vivo activities indicates that optimization of their pharmacokinetic properties may yield compounds with greater bioavailabilities and better antischistosomiasis activities in vivo.

Mechanochemical solid-state synthesis of 2-aminothiazoles, quinoxalines and benzoylbenzofurans from ketones by one-pot sequential acid- and base-mediated reactions

α-Chloroketones-obtained by the atom-economical chlorination of ketones with trichloroisocyanuric acid (TCCA) in the presence of p-TSA under ball-milling conditions-were set up for a sequential base-mediated condensation reaction with thiourea/thiosemicarbazides, o-phenylenediamine and salicylaldehyde to afford 2-aminothiazoles, 2-hydrazinylthiazoles, quinoxalines and benzoylbenzofurans, respectively, in respectable yields. The viability of one-pot sequential acid- and base-mediated reactions in the solid state under ball-milling conditions is thus demonstrated.

A Combined Experimental and Theoretical Study of the Ammonium Bifluoride Catalyzed Regioselective Synthesis of Quinoxalines and Pyrido[2,3- b ]pyrazines

Ammonium bifluoride was efficiently used at a 0.5 mol% loading to catalyze the cyclocondensation of 1,2-arylenediamines with 1,2-dicarbonyl compounds at room temperature in methanol-water to give quinoxalines or pyrido[2,3-b]pyrazines in excellent yields. Importantly, 2,8-disubstituted quinoxalines and 3-substituted pyrido[2,3-b]pyrazines were regioselectively formed by the reaction of arylglyoxals with 3-methylbenzene-1,2-diamine or pyridine-2,3-diamine, respectively. An analysis of the density functional theory reactivity indices explained the catalytic role of ammonium bifluoride.

Saccharin as an organocatalyst for quinoxalines and pyrido[2,3-b[pyrazines Syntheses

A room-temperature procedure using saccharin as catalyst has been described for the cyclocondensation of different 1,2-arylenediamines with various 1,2-dicarbonyl compounds, yielding either quinoxalines or pyrido[2,3-b] pyrazines. The reactions proceed in very short reaction times in methanol, and the target heterocycles are isolated in quantitative yields after addition of water, filtration, and drying. Substituted pyrido[2,3-b]pyrazines can also be reached regioselectively by reacting α-ketoaldehydes with 2,3-diaminopyridine. Taylor and Francis Group, LLC.

Graphite catalyzed green synthesis of quinoxalines

A new simple approach using environmentally benign, cheap, and easily recyclable graphite as a heterogeneous catalyst for the synthesis of quinoxalines is described. A library of pharmacologically interesting diphenylquinoxalines is prepared by the double condensation of substituted benzils, phenanthrene-9,10-dione, and benzoin with aromatic diamines in 71-93% yields at room temperature in ethanol. Aliphatic diamines gave corresponding dihydropyrazines from substituted benzils in 72-92% yields.

Et3N-catalyzed oxidative dehydrogenative coupling of α-unsubstituted aldehydes and ketones with aryl diamines leading to quinoxalines using molecular oxygen as oxidant

A novel Et3N-catalyzed oxidative dehydrogenative coupling of α-unsubstituted carbonyl compounds with aryl diamines leading to quinoxaline derivatives using molecular oxygen as oxidant has been developed. Six hydrogen dissociations involving 2 sp3 C-H bonds activation are realized under mild conditions in this approach. Plausible mechanism is proposed for this novel Et3N-catalyzed transformation on the basis of the aboratively designed mechanistic studies including the radical detection by EPR. 2012 Elsevier Science. All rights reserved.

Synthesis of quinoxaline analogues

Substituted tricyclic or tetracyclic quinoxalines, tricyclic pyridoquinoxalines and bis-quinoxalines were synthesized in high yields starting from cyclic ketones by the -bromination of cyclic ketones with N-bromosuccinimide (NBS) followed by condensation of the resulting -bromo ketones with 1,2-diaminobenzene, 3,4-diaminopyridine, or 3,3-diaminobenzidine. Georg Thieme Verlag Stuttgart New York.

Tandem radical reactions of isonitriles with 2-pyridonyl and other aryl radicals: Scope and limitations, and a first generation synthesis of (±)-camptothecin

Photolysis of N-propargyl-6-halo-2-pyridones and related aromatic halides in the presence of aryl isonitriles provides tetra- and penta-cyclic products in a single step by a sequence of radical addition to the isonitrile followed by two cyclizations. The scope and limitations of the process are described along with a first generation synthesis of racemic camptothecin.