531-46-4

Usage

Uses

Used in Pharmaceutical Industry:
5,12-Dihydroquinoxalino[2,3-b]quinoxaline is used as a NOX1-specific inhibitor for targeting the excessive ROS production associated with intestinal mucosa damage, inflammatory bowel disease, and prostate cancer. By inhibiting NOX1, 5,12-dihydroquinoxalino[2,3-b]quinoxaline can potentially reduce the harmful effects of ROS and provide therapeutic benefits in treating these conditions.

Upstream product

• 6640-47-7 2,3-diaminoquinoxaline 
• 95-54-5 1,2-diamino-benzene 
• 2213-63-0 2,3-dichloroquinoxaline 
• 15804-19-0 quinoxaline-2,3-dione 
• 144-62-7 oxalic acid 
• 258-14-0 Chinoxalino<2,3-b>chinoxalin 
• 166271-34-7 N-(3-chloroquinoxalin-2-yl)-benzenesulfonamide 
• 64-17-5 ethanol 
• 102880-02-4 1,2-dibutoxy-tetrachloro-ethane 
• 471-46-5 Oxalamide 
• 124831-91-0 3-(α-chlorobenzyl)-1,2-dihydroxyquinoxalin-2-one 

Downstream Products

• 91362-51-5 N-(1H-Benzoimidazol-2-ylmethyl)-benzene-1,2-diamine 
• 258-14-0 Chinoxalino<2,3-b>chinoxalin 

Relevant academic research and scientific papers

A surprising formation of novel bridged bis-benzimidazoles by oxidation of diaminoquinoxalines

A synthesis of novel hexacyclic bis-benzimidazoles 6 starting from 2,3-diarylamino-quinoxalines via an oxidative cyclization cascade is described. These very stable and high-melting derivatives are featured by their strong fluorescence in the blue region of the visible spectrum. The cyclization reaction between 2,3-dichloroquinoxaline and 1,2-phenylenediamine did not lead to derivatives of type 6. In this case, only fluoflavine 7 was isolated quantitatively.

The use of diethylene glycol in the synthesis of 2,2'-bibenzimidazole from o-phenylenediamine and oxalic acid

One- and two-step syntheses of 2,2'-bibenzimidazole were compared. Diethylene glycol was used as solvent that provides good solubility of the substrates. The limitation of the one-step preparation is the formation of the by-product, fluoflavine. The two-step synthesis proceeds with the separation of the intermediate product, 1,4-dihydroquinoxaline-2,3-dione, and the final product is only 2,2'-bibenzimidazole. The total yield of the two-step synthesis is above 85%.

Synthesis and characterization of electron-accepting nonsubstituted tetraazaacene derivatives

Oligoacenes are of interest as organic p-type semiconductors for use in electronic devices, but their use as n-type semiconductors is limited. N-Heteroacenes have been investigated as oligoacene-based n-type semiconductors due to their enhanced electron affinity. Herein, we report the synthesis, X-ray crystal structures, electrochemical, and field-effect transistor properties of TANC and BTANC.

Efficient synthesis and characterization of novel bibenzimidazole oligomers and polymers as potential conjugated chelating ligands

A simple and mild condensation route for the synthesis of novel bibenzimidazole oligomers and polymers is reported here using methyl 2,2,2-trichloroacetimidate as a key starting material. The dimer, trimer, tetramer, and polymers of bibenzimidazole were synthesized as a new series of potential conjugated chelating ligands for metallopolymer studies. The polymers show a maximum absorption at around 400 nm. The optical band gap of the polymer was estimated to be 2.68 eV.

Quantitative cascade condensations between o-phenylenediamines and 1,2-dicarbonyl compounds without production of wastes

o-Phenylenediamines 1 underwent a series of cascade condensations with 1,2-dicarbonyl compounds to afford quantitative yields (eight cases) of heterocycles in solid-state syntheses that avoided waste formation. The products were produced in pure form and did not require purifying workup. The components were ball-milled in stoichiometric ratio, or in exceptional cases they were melted together and heated in the absence of solvents (some of them giving quantitative yields). Benzils and 2-hydroxy-1,4-naphthoquinone afforded quinoxaline derivatives 3 and 5, 2-oxoglutaric acid gave a 3-oxodihydroquinoxaline 7, and oxalic acid afforded the dihydroquinoxaline-2,3-dione 9. This last condensed with la in the melt, to afford a mixture of bis(benzimidazolyl) 10 and fluoflavin 11. Alloxane hydrate provided a 100% yield of the 3-oxodihydroquinoxaline-2-carbonylureas 15/16 at room temperature. Parabanic acid required a melt reaction providing a 78% yield of 3-oxodihydroquinoxalinyl-2-urea 22 and side products. Despite numerous reaction steps, most of these uncatalyzed stoichiometric reactions proceeded quantitatively in the solid state to give only one product (plus water), with unsurpassed atom economy. If catalysis with HCl was tried, the results were inferior. If melt reactions were required it appeared to be advantageous to have the products crystallize directly at the reaction temperature. The synthetic results have been interpreted mechanistically and compared to some similar solution reactions that do not exhibit the benefits of the solid-state techniques. Wiley-VCH Verlag GmbH, 69451 Weinheim, Germany, 2002).

SYNTHESIS, STRUCTURE, AND CHEMICAL PROPERTIES OF SOME N-(3-CHLORO-2-QUINOXALYL)ARYLSULFONAMIDES

We have developed a method for synthesis of N-(3-chloro-2-quinoxalyl)sulfonamides by reaction of 2,3-dichloroquinoxaline with substituted arylsulfonamides.Based on the IR spectra, we have established that in the solid state, the synthesized compounds exis

Electrochemical reduction of quinoxalinoquinoxaline

The electrochemical reduction of quinoxalinoquinoxaline gives fluoflavine (2) the structure of which is discussed.The electrochemical reduction of fluoflavine in acidic medium leads to a hexahydroquinolinoquinoxaline.A reduction mechanism is proposed based on cyclic voltammetry results and preparative electrolysis.The results obtained in the case of quinoxalinoquinoxaline are used to rationalize the results obtained in the case of pyrazinopyrazines and pyrazinoquinoxalines.