67170-62-1

Upstream product

• 15462-02-9 2-ethoxy-1-(3,4-dimethoxy-phenyl)-2-hydroxy-ethanone 
• 95-54-5 1,2-diamino-benzene 
• 1835-02-5 2-Bromo-1-(3,4-dimethoxyphenyl)ethanone 
• 120-20-7 2-(3,4-dimethoxyphenyl)-ethylamine 
• 88-74-4 2-nitro-aniline 
• 1131-62-0 1-(3,4-dimethoxyphenyl)ethanone 
• 100537-41-5 4-quinoxalin-2-yl-pyrocatechol 
• 77-78-1 dimethyl sulfate 

Relevant academic research and scientific papers

Copper-catalyzed aerobic oxidative coupling of o-phenylenediamines with 2-aryl/heteroarylethylamines: direct access to construct quinoxalines

A copper-catalyzed oxidative coupling reaction of o-phenylenediamines with 2-aryl/heteroarylethylamines using molecular oxygen as an oxidant has been developed. This approach provides a practical and direct access to construct quinoxalines in excellent yields at room temperature. The reaction has a broad substrate scope and exhibits excellent functional-group tolerance. This method could be easily scaled up and applied to the synthesis of biologically active molecules bearing a quinoxaline structural scaffold.

Green synthesis of novel quinoxaline sulfonamides with antibacterial activity

A facile and efficient method was investigated for the synthesis of different quinoxalines by the reaction of o-phenylene diamine and 2-bromoacetophenones. This procedure was carried out in ethanol under catalyst-free conditions. Several sulfonamides were synthesized from 2-(4-methoxyphenyl)-quinoxaline in two steps. At first chlorosulfonation of 2-(4-methoxyphenyl) quinoxaline was done using chlorosulfonic acid and led to 2-methoxy-5-quinoxalin-2-yl-benzenesulfonyl chloride. Then quinoxaline sulfonamides were synthesized by the reaction of quinoxaline sulfonyl chloride with different aromatic amines under solvent-free conditions. All the products were obtained in excellent yields after an easy work-up and were evaluated for antibacterial activities against Staphylococcus spp. and Escherichiacoli bacteria.

Searching for Novel Inhibitors of the S. aureus NorA Efflux Pump: Synthesis and Biological Evaluation of the 3-Phenyl-1,4-benzothiazine Analogues

Bacterial resistance to antimicrobial agents has become an increasingly serious health problem in recent years. Among the strategies by which resistance can be achieved, overexpression of efflux pumps such as NorA of Staphylococcus aureus leads to a sub-lethal concentration of the antibacterial agent at the active site that in turn may predispose the organism to the development of high-level target-based resistance. With an aim to improve both the chemical stability and potency of our previously reported 3-phenyl-1,4-benzothiazine NorA inhibitors, we replaced the benzothiazine core with different nuclei. None of the new synthesized compounds showed any appreciable intrinsic antibacterial activity, and, in particular, 2-(3,4-dimethoxyphenyl)quinoline (6 c) was able to decrease, in a concentration-dependent manner, the ciprofloxacin MIC against the norA-overexpressing strains S. aureus SA-K2378 (norA++) and SA-1199B (norA+/A116E GrlA).

A simple and straightforward approach to quinoxalines by iron/sulfur-catalyzed redox condensation of o-nitroanilines and phenethylamines

In situ generated iron sulfide from elemental sulfur and ferric chloride was found to be a highly efficient catalyst for the redox condensation cascade reaction between o-nitroanilines and 2-arylethylamines. This method constitutes a new atom-, step-, and redox-economical route to 2-arylquinoxalines.

Synthesis of functionalized benzimidazoles and quinoxalines catalyzed by sodium hexafluorophosphate bound Amberlite resin in aqueous medium

A very simple, eco-friendly, and versatile method for the selective synthesis of 1,2-disubstituted benzimidazoles and quinoxalines in water-methanol (1:1) mixture with the aid of resin bound hexafluorophosphate ion as catalyst is reported. The method is also effective for the incorporation of quinoxaline nucleus at the A ring of pentacyclic triterpenoid, friedelin. A plausible mechanism for the formation of disubstituted benzimidazole has also been suggested.

Synthesis of functionalized benzimidazoles and quinoxalines catalyzed by sodium hexafluorophosphate bound Amberlite resin in aqueous medium

A very simple, eco-friendly, and versatile method for the selective synthesis of 1,2-disubstituted benzimidazoles and quinoxalines in water-methanol (1:1) mixture with the aid of resin bound hexafluorophosphate ion as catalyst is reported. The method is also effective for the incorporation of quinoxaline nucleus at the A ring of pentacyclic triterpenoid, friedelin. A plausible mechanism for the formation of disubstituted benzimidazole has also been suggested.

Synthesis of libraries of quinoxalines through eco-friendly tandem oxidation-condensation or condensation reactions

A facile and expeditious solid-phase synthesis of libraries of quinoxalines promoted on KF-alumina surface via tandem oxidation-condensation or condensation reactions is reported. The reaction protocol is operationally simple and mild. Moreover, solvent-free reaction condition makes the reaction procedure eco-friendly and economically viable.