25187-19-3

Upstream product

• 532-54-7 oxo-phenyl-acetaldehyde oxime 
• 95-83-0 4-Chloro-1,2-phenylenediamine 
• 1076-59-1 3-phenyl-4H-isoxazol-5-one 
• 38622-91-2 [(p-methylphenyl)sulfonylmethyl]isonitrile 
• 100-52-7 benzaldehyde 
• 582-24-1 1-phenyl-2-hydroxyethanone 
• 98-86-2 acetophenone 
• 4636-16-2 iodoacetophenone 
• 31541-36-3 3-benzoylmethylidene-2-oxindole 
• 20913-05-7 (Benzoylmethylene)triphenylphosphorane 
• 64-04-0 phenethylamine 
• 89-63-4 4-Chloro-2-nitroaniline 
• 100-41-4 ethylbenzene 
• 100-42-5 styrene 

Downstream Products

• 57433-56-4 2-Phenyl-6-chlorchinoxalin-4-oxid 
• 1221687-19-9 (R)-6-chloro-2-phenyl-1,2,3,4-tetrahydroquinoxaline 

Relevant academic research and scientific papers

Iron-catalyzed one-pot synthesis of quinoxalines: Transfer hydrogenative condensation of 2-nitroanilines with vicinal diols

Here, we report iron-catalyzed one-pot synthesis of quinoxalines via transfer hydrogenative condensation of 2-nitroanilines with vicinal diols. The tricarbonyl (η4-cyclopentadienone) iron complex, which is well known as the Kn?lker complex, catalyzed the oxidation of alcohols and the reduction of nitroarenes, and the corresponding carbonyl and 1,2-diaminobenzene intermediates were generated in situ. Trimethylamine N-oxide was used to activate the iron complex. Various unsymmetrical and symmetrical vicinal diols were applied for transfer hydrogenation, resulting in quinoxaline derivatives in 49-98% yields. A plausible mechanism was proposed based on a series of control experiments. The major advantages of this protocol are that no external redox reagents or additional base is needed and that water is liberated as the sole byproduct. This journal is

Ionic-Liquid-Catalyzed Synthesis of Imines, Benzimidazoles, Benzothiazoles, Quinoxalines and Quinolines through C?N, C?S, and C?C Bond Formation

We report the tetramethyl ammonium hydroxide catalyzed oxidative coupling of amines and alcohols for the synthesis of imines under metal-free conditions by utilizing oxygen from air as the terminal oxidant. Under the same conditions, with ortho-phenylene diamines and 2-aminobenzenethiols the corresponding benzimidazoles and benzothiazoles were obtained. Quinoxalines were obtained from ortho-phenylene diamines and 1-phenylethane-1,2-diol, the conditions were then extended to the synthesis of quinoline building blocks by reaction of 2-amino benzyl alcohols either with 1-phenylethan-1-ol or acetophenone derivatives. The formation of C?N, C?S and C?C bonds was achieved under metal-free conditions. A broad range of amines (aromatic, aliphatic, cyclic and heteroaromatic) as well as benzylic alcohols including heteroaryl alcohols reacted smoothly and provided the desired products. The mild reaction conditions, commercially available catalyst, metal-free, good functional-group tolerance, broad range of products (imines, benzimidazoles, benzothiazoles, quinoxalines and quinolines) and applicability at gram scale reactions are the advantages of the present strategy.

Iron(II)-Catalyzed Aerobic Biomimetic Oxidation of N-Heterocycles

Herein, an iron(II)-catalyzed biomimetic oxidation of N-heterocycles under aerobic conditions is described. The dehydrogenation process, involving several electron-transfer steps, is inspired by oxidations occurring in the respiratory chain. An environmentally friendly and inexpensive iron catalyst together with a hydroquinone/cobalt Schiff base hybrid catalyst as electron-transfer mediator were used for the substrate-selective dehydrogenation reaction of various N-heterocycles. The method shows a broad substrate scope and delivers important heterocycles in good-to-excellent yields.

Visible light promoted tandem dehydrogenation-deaminative cyclocondensation under aerobic conditions for the synthesis of 2-aryl benzimidazoles/quinoxalines fromortho-phenylenediamines and arylmethyl/ethyl amines

Visible light promoted domino synthesis of 2-aryl benzimidazoles is reported through the reaction ofortho-phenylenediamines and arylmethyl amines under aerobic conditions. The methodology has wide substrate scope and tolerates a wide range of functional groups affording the products in high yields. The use of arylethyl amines instead of arylmethyl amines gives 2-aryl quinoxalines.

A heterogeneous catalytic strategy for facile production of benzimidazoles and quinoxalines from primary amines using the Al-MCM-41 catalyst

This study reports a straightforward heterogeneous catalytic (Al-MCM-41) approach to synthesize nitrogen heterocycle moieties from primary amines under solvent-free conditions. The Al-MCM-41 catalyst was prepared using a hydrothermal method and characterized by various analytical techniques. The probability and limitations of the catalytic methodology were presented with various substrates. The catalytic method grants an attractive route to a wide variety of benzimidazole and quinoxaline moieties with good to excellent yields. The gram scale reaction and reusability (up to five cycles) of the Al-MCM-41 catalyst would greatly benefit industrial applications. This journal is

A quantum-chemical approach to develop tetrahydroquinoxaline as potent ferroptosis inhibitors

Ferroptosis is a recently characterized form of regulated necrosis with the iron-dependent accumulation of (phospho)lipid hydroperoxides (LOOH). It has attracted considerable attention for its putative involvement in diverse pathophysiological processes, such as cardiovascular disease and neurodegeneration. Here we describe the discovery of tetrahydroquinoxaline, a novel scaffold of ferroptosis inhibitors based on quantum chemistry methods. Tetrahydroquinoxaline deviates showed very good inhibition of ferroptosis, while being non cytotoxic for human cancer cells. And, the advantage of them is their small molecular weight (MW. = 148 Da) that can be coupled with other drugs to form multi-target drugs to better meet the treatment of complicated diseases.

Nickel-Catalyzed Direct Synthesis of Quinoxalines from 2-Nitroanilines and Vicinal Diols: Identifying Nature of the Active Catalyst

The inexpensive and simple NiBr2/1,10-phenanthroline system-catalyzed synthesis of a series of quinoxalines from both 2-nitroanilines and 1,2-diamines is demonstrated. The reusability test for this system was performed up to the seventh cycle, which afforded good yields of the desired product without losing its reactivity significantly. Notably, during the catalytic reaction, the formation of the heterogeneous Ni-particle was observed, which was characterized by PXRD, XPS, and TEM techniques.

Iridium-Catalyzed Carbenoid Insertion of Sulfoxonium Ylides for Synthesis of Quinoxalines and β-Keto Thioethers in Water

Sulfoxonium ylides as safe carbene precursors are described for iridium-catalyzed carbene insertions and annulation, providing a facile and green approach to access a variety of quinoxaline derivatives in water. This water-mediated method also allows the preparation of β-keto thioethers under mild condition.

Bonded- A nd discreted-Lindqvist hexatungstate-based copper hybrids as heterogeneous catalysts for the one-pot synthesis of 2-phenylquinoxalines: Via 2-haloanilines with vinyl azides or 3-phenyl-2 H-azirines

One bonded- A nd one discreted-Lindqvist hexatungstate-based copper hybrids (Cu-POMs) ([Cu2(O)OH (phen)2]2[W6O19]?6H2O (1) and [Cu2(phen)4Cl] [HW6O19]?2H2O (2) (phen = 1,10-phenanthroline)) were controllably synthesized and routinely characterized. Cu-POM

Cooperative iridium complex-catalyzed synthesis of quinoxalines, benzimidazoles and quinazolines in water

Herein, an efficient methodology for the synthesis of a diverse class of N-heterocyclic moieties, such as quinoxalines, benzimidazoles and quinazolines, was developed in water using bio-renewable alcohols. The quinoxalines were successfully synthesized from a wide range of diamines and nitroamines with diols in air. Interestingly, benzimidazoles and quinazolines were synthesized with excellent isolated yields without using any external base. Finally, the preparative scale synthesis of various N-heterocycles and pharmaceutically active quinoxalines established the practicability of this protocol. For this iridium system, a metal-ligand cooperative mechanism was proposed based on kinetic and DFT studies.