6639-86-7

Usage

Chemical Properties

Yellow Solid

Uses

Quinoxaline derivative. Bactericidal activity.

InChI:InChI=1/C9H8N2O2/c1-7-6-10(12)8-4-2-3-5-9(8)11(7)13/h2-6H,1H3

Upstream product

• 7251-61-8 2-methylquinoxaline 
• 480-96-6 benzofurazan oxide 
• 24309-97-5 N-(2-hydroxyethyl)-3-oxobutanamide 
• 105686-38-2 N,N-Dimethyl-3-(trimethylsilyl)-1-propen-1-amin 
• 67-64-1 acetone 
• 74200-06-9 3-methyl-1,4-dioxide-quinoxaline-2-carboxylic acid 
• 18916-45-5 3-Methylquinoxaline 1-Oxide 
• 6795-30-8 3-methylquinoxaline-2-carboxaldehyde-1,4-di-N-oxide 
• 123-75-1 pyrrolidine 
• 4202-14-6 dimethyl (2-oxopropyl)phosphonate 
• 123-38-6 propionaldehyde 
• 1322877-87-1 C₆H₄N₂O₂*C₄₂H₇₀O₃₅ 
• 88-74-4 2-nitro-aniline 
• 236092-93-6 benzofuroxane N-oxide 

Downstream Products

• 17626-51-6 1,4-dioxoquinoxaline-2-carboxaldehyde 
• 18080-66-5 2-(bromomethyl)quinoxaline 1,4-dioxide 
• 84125-21-3 2-{(E)-2-[5-(4-Chloro-phenyl)-furan-2-yl]-vinyl}-quinoxaline 1,4-dioxide 
• 84137-87-1 4-{5-[(E)-2-(1,4-Dioxy-quinoxalin-2-yl)-vinyl]-furan-2-yl}-benzoic acid ethyl ester 
• 84285-55-2 2-(1,4-Dioxy-quinoxalin-2-yl)-1-[5-(4-nitro-phenyl)-furan-2-yl]-ethanol 
• 84125-17-7 2-<β-(o-Chlorophenyl)vinyl>quinoxaline di-N-oxide 
• 84125-12-2 1-(2-Chloro-phenyl)-2-(1,4-dioxy-quinoxalin-2-yl)-ethanol 
• 84125-16-6 2-[(E)-2-(4-Nitro-phenyl)-vinyl]-quinoxaline 1,4-dioxide 
• 84125-11-1 2-(1,4-Dioxy-quinoxalin-2-yl)-1-(4-nitro-phenyl)-ethanol 
• 84125-18-8 2-<β-(2,4-Dichlorophenyl)vinyl>quinoxaline di-N-oxide 
• 84125-13-3 1-(2,4-Dichloro-phenyl)-2-(1,4-dioxy-quinoxalin-2-yl)-ethanol 
• 7251-61-8 2-methylquinoxaline 
• 17357-92-5 3-methylquinoxaline-2-carboxamide 
• 80765-49-7 2-phenacylidene-3-methyl-1H-quinoxaline 4-oxide 

Relevant academic research and scientific papers

Synthesis and Biological Evaluation of New Quinoxaline Derivatives as Antioxidant and Anti-Inflammatory Agents

We report the synthesis, anti-inflammatory, and antioxidant activities of novel quinoxaline and quinoxaline 1,4-di-N-oxide derivatives. Microwave-assisted methods have been used to optimize reaction times and to improve yields. The tested compounds presented important scavenging activities and promising in vitro inhibition of soybean lipoxygenase (LOX). Two of the best LOX inhibitors (compounds 7b and 8f) were evaluated as invivo anti-inflammatory agents using the carrageenin-induced edema model. One of them (compound 7b) showed important in vivo anti-inflammatory effect (41%) similar to that of indomethacin (47%) used as the reference drug. Synthesis and Biological Evaluation of New Quinoxaline Derivatives as Antioxidant and Anti-Inflammatory Agents Asuncion Burguete, Eleni Pontiki, Dimitra Hadjipavlou-Litina*, Saioa Ancizu, Raquel Villar, Beatriz Solano, Elsa Moreno, Enrique Torres, Silvia Perez, Ignacio Aldana and Antonio Monge The synthesis, anti-inflammatory and antioxidant activities of new quinoxaline derivatives are reported. The new compounds exhibit important scavenging activities and promising values of in vitro inhibition of soybean LOX, One of them shows strong in vivo anti-inflammatory effect similar to that of indomethacin used as the reference drug.

Effective promotion of beirut reaction by-cyclodextrin in water

A mild and highly efficient, environmentally friendly procedure has been developed for the conversion from benzofurazan-N-oxides to quinoxaline di-N-oxides in the presence of-cyclodextrin in water at room temperature with excellent yields. The application of cyclodextrin precludes the use of organic solvent, and the catalyst can be recovered and reused in subsequent reactions with the same catalytic activity. Herein, the Beirut reaction is carried out in the medium of water for the first time. The reaction mechanism was proposed based on the inclusion complexation of-cyclodextrin with benzofurazan-N-oxides which was confirmed by 1H NMR, ultraviolet/visible spectrum, and infrared spectroscopy. Copyright

First synthesis of 2-phosphonylated quinoxaline 1,4-dioxides: An extension to the Beirut reaction

An extension of the Beirut reaction for the preparation of the first members of the 2-phosphonylated quinoxaline 1,4-dioxide series is described. Contrary to their carboxylated equivalents, preparation of these new compounds could not be achieved under basic conditions but required the use of powdered molecular sieves. Good and reproducible yields were obtained only when the initial suspension in THF was transformed into a pasty film by slow evaporation of ca. 90% of the initial solvent volume.

A new efficient route for the formation of quinoxaline N-oxides and N,N′-dioxides using HOF·CH3CN

HOF·CH3CN, a very efficient oxygen-transfer agent made readily from fluorine and aqueous acetonitrile, was reacted with various quinoxaline derivatives to give the corresponding mono N-oxides and especially the N,N′-dioxides in very good yields under mild conditions and short reaction times.

An Improved and Efficient Synthesis of Quinoxalinecarboxamide 1,4-Dioxides from Benzofuroxan and Acetoacetamides in the Presence of Calcium Salts

An improved and efficient method for the preparation of the title compounds 3 is described.Thus, quinoxalinecarboxamide 1,4-dioxides 3 are synthesized in high yields by reaction of benzofuroxan 1 with acetoacetamides 2 in the presence of catalytic amounts of calcium salts and ethanolamine.The reaction is assumed to involve a chelate mechanism with 4 as intermediate.Side reactions are studied by means of HPLC and TLC.

Silylenamines as Synthons for Silylated Heterocycles

The silylenamines 1a-c react with different unsaturated electrophiles to form cyclic adducts containing sulfur (2, 4, 17) oxygen (10, 14, 22), and nitrogen (19, 20, 21) in the ring.The reaction of 1a with acetylenedicarboxylate leads to the cyclobutene 8 which is opened to the pentadiene 9c, whereby the regioselectivity typical for enamines is always observed.

Quinoxaline derivatives

The synthesis of quinoxaline and benzimidazole-N-oxides and of ester and amide derivatives of 3-hydroxy-2-quinoxalinecarboxylic acid by a novel process consisting of the reaction between a benzofuroxan and an activated methylene-containing compound under basic conditions.

Cosmetic composition for imparting to human skin a coloration resembling a natural tan

A cosmetic composition for imparting to human skin after exposure to sunlight a coloration resembling a natural tan comprises a cosmetic vehicle suitable for topical application to the skin and an effective amount of at least one compound of the formula STR1 wherein R1 and R2 each independently represent hydrogen, an aliphatic radical having 1-18 carbon atoms, carbalkoxy having 2-5 carbon atoms, acyl having 2-5 carbon atoms, aryl, aryl substituted by alkyl having 1-4 carbon atoms or hydroxy, a heterocycle containing 4-6 members, substituted or not by alkyl having 1-4 carbon atoms, halogen or hydroxy, or R1 and R2 together form a saturated ring containing 4-12 chains, optionally substituted by alkyl having 1-4 carbon atoms, halogen or hydroxy, or bridged and containing a heteroatom selected from N, O or S; and R3 represents hydrogen, a lower aliphatic group containing 1-6 carbon atoms, lower alkoxy containing 1-4 carbon atoms or halogen, with the proviso that R1, R2 and R3 are not hydrogen simultaneously; and an acid addition salt thereof.