119426-73-2

Upstream product

• 89-62-3 4-methyl-2-nitroaniline 
• 610-39-9 3,4-Dinitrotoluene 
• 33609-48-2 3,4-dinitrobenzophenone 
• 528-45-0 3,4-dinitrobenzoic acid 
• 39070-63-8 4-benzoylbenzene-1,2-diamine 
• 431-03-8 dimethylglyoxal 
• 6971-33-1 4-methyl-2-nitro-1-nitrosobenzene 

Downstream Products

• 119426-46-9 5-(2',3'-Dimethyl-quinoxalin-6'-yl)-5-phenyl-imidazolidine-2,4-dione 

Relevant academic research and scientific papers

Ionic liquid functionalized cellulose as an efficient heterogeneous catalyst for the facile and green synthesis of benzoxazine, pyrazine and quinoxaline derivatives in aqueous media

Immobilization of acidic ionic liquid, 1-methyl-3-(3-trimethoxysilylpropyl) imidazolium hydrogen sulfate on cellulose (Cell-[pmim]HSO4) as an efficient heterogenous catalyst for the simple and environmentally benign synthesis of benzoxazine, pyrazine and quinoxaline derivatives in aqueous media at room temperature is described. The catalyst was characterized by FTIR spectroscopy and X-ray diffraction pattern. This method provides several advantages such as mild reaction conditions, environmentally friendly catalyst, good to excellent yields and simple work-up procedure.

Microwave-assisted synthesis of quinoxaline derivatives using glycerol as a green solvent

A rapid, efficient, and reliable catalyst-free procedure for the synthesis of quinoxaline derivatives in glycerol under focused microwave irradiation was developed. The reaction proceeded in glycerol without any catalyst making this methodology valuable from both economic and environmental viewpoints.

Synthesis of quinoxaline derivatives catalyzed by PEG-400

Polyethylene glycol (PEG) was found to be an effective catalyst for the condensation of 1,2-diamines with 1,2-dicarbonyl compounds to afford the corresponding quinoxaline derivatives in excellent yields under mild reaction conditions.

An experimental and theoretical study of intramolecular regioselective oxidations of 6-substituted 2,3-dimethylquinoxaline derivatives

An experimental and theoretical study of the regioselective Riley oxidation was conducted on a series of 2,3-dimethyl-6-substituted-quinoxalines bearing EWG (NO2, CN, CF3, Cl, Br, F, COOH, COOMe, COPh) and EDG (2,3-dimethylquinoxaline, OMe, OH, NH2) substituents. The nitrogen lone pair of electrons of the symmetric benzopyrazine moiety initiates the oxidation and promotes nucleophilic competition between the two active sites to give carbaldehyde regioisomers a and b. The mesomeric effect provides the dominant contribution to the regioselectivity. The compounds were characterized by NMR, measuring the 1H, 13C, pfg-HSQC, pfg-HMBC, and 15N, 1H correlation signals established by pfg-HMQC. The nucleophilic reactivity of nitrogen was evaluated by 1H NMR titration and analyzed using Perrin linearization to determine the reactivity ratio, ΔK, of the N4 and N1 nitrogen atoms. The structures were optimized using density functional theory at the ωB97XD/6-311G++(d,p) level of theory. The highest occupied molecular orbitals modeled using the HF/6-311G++(d,p) functionals revealed an asymmetric electron density that confirmed the asymmetric nucleophilicity of the nitrogen centers. These values agreed with the experimentally measured ΔK ratios. The PM6 theoretical calculations of the heats of formation of the mesomeric forms and intermediates of (2,3-dimethyl-6-substituted-quinoxalines)-SeO2 allowed us to identify the reaction routes that minimized energy expenditures. The regioselectivities were explained in terms of the energetic diagrams of the regioisomers. All compounds evaluated indicated a preference toward forming regioisomer b, except for the derivative bearing the EDG substituent (2,3-dimethylquinoxaline) which displayed a preference for regioisomer a.

Microwave-assisted synthesis of quinoxalines in peg-400

A rapid and efficient procedure for the synthesis of quinoxaline derivatives has been achieved by condensation of aryl-1,2-diamines with 1,2-dicarbonyl compounds catalyzed by polyethylene glycol under CEM-focused microwave-irradiation conditions. Copyright

6-Lithioquinoxalines and Their Transformations

6-Bromo-2,3-diphenylquinoxaline reacts with butyllithium to give the 6-lithio derivative in a yield of more than 80%, which reacts with electrophiles such as benzophenone, Michler ketone, methyl ethyl ketone, iodine, selenium, and dimethylformamide to give the corresponding quinoxaline derivatives. 6-Bromo-2,3-dimethylquinoxaline is metallated with butyl- and phenyllithium at the methyl groups and benzene ring. These organolithium compounds react with benzophenone to give the corresponding diphenyl- and triaryl-carbinols, whose yield and ratio were determined by HPLC. These results open prospects for preparing new quinoxaline derivatives substituted at the annelated benzene ring.

Reactions of 4-benzoyl-o-phenylenediamine: Synthesis of dihydro-1,5-benzodiazepines, quinoxalines and benzimidazoles

Condensation of 4-benzoyl-o-phenylenediamine (1) with different ketones under mild conditions using acetic acid as catalyst results in dihydro-benzodiazepines, quinoxalines and benzimidazoles.