13362-56-6

Upstream product

• 3171-45-7 4,5-dimethyl-1,2-phenylenediamine 
• 134-81-6 benzil 
• 451-40-1 phenyl benzyl ketone 
• 119-53-9 2-hydroxy-2-phenylacetophenone 
• 17059-74-4 3-(Dimethylamino)-1,2-diphenyl-2-propen-1-on 
• 5088-12-0 (E)-2-bromo-1,2-diphenylethenyl acetate 
• 501-65-5 diphenyl acetylene 
• 6972-71-0 4,5-dimethyl-2-nitrobenzenamine 
• 492-70-6 1,2-diphenyl-1,2-ethanediol 
• 1684-14-6 2,3-diphenylquinoxaline 
• 95-54-5 1,2-diamino-benzene 

Downstream Products

• 282528-05-6 6,7-bis(bromomethyl)-2,3-diphenylquinoxaline 
• 1117700-52-3 diethyl 1,4-dihydro-6,7-dimethyl-2,3-diphenylquinoxaline-1,4-dicarboxylate 
• 1117700-48-7 6,7-dimethyl-2a,3-diphenylazetidino[1,2-a]quinoxaline 
• 1262801-97-7 6,7-dimethyl-2,3-bis(2-nitrophenyl)quinoxaline 
• 1296867-24-7 C₂₆H₂₂N₂O₄ 
• 282528-08-9 2,3-diphenyl-8,9-dihydro-6H-8λ⁴-[1,2]oxathiino-[4,5-g]quinoxalin-8-one 

Relevant academic research and scientific papers

An environmentally friendly, cost effective synthesis of quinoxalines: The influence of microwave reaction conditions

A convenient, environmentally friendly and novel synthesis of quinoxalines using silica gel as the catalyst is described. The choice of microwave conditions has been shown to have a substantial impact on the reaction outcome with closed-vessel microwave irradiation resulting in the formation of quinoxalines in high yields and short reaction times. Preliminary mechanistic investigations have indicated that a slight build-up in pressure has a major impact on the reaction outcome.

One-pot aqueous-phase synthesis of quinoxalines through oxidative cyclization of deoxybenzoins with 1,2-phenylenediamines catalyzed by a zwtterionic Cu(II)/calix[4]arene complex

A green protocol for the synthesis of quinoxalines has been developed from catalytic oxidative cyclization of deoxybenzoins with 1,2-phenylenediamines in water. The optimal conditions are involved in the use of a water-soluble mononuclear copper(II) complex of a zwitterionic calix[4]arene [Cu(II)L(H2O)]I2 (1, H4L?=?[5,11,17,23–tetrakis (trimethylammonium)–25,26,27,28–tetrahydroxycalix[4]arene]) as a catalyst in alkali solution after refluxing for 15?h in O2. The target quinoxaline and its derivatives were obtained in good yields (up to 88%). The procedure described in this paper is simple, practical and environmentally benign.

An environmentally benign attribute for the expeditious synthesis of quinoxaline and its derivatives

A simple, efficient, and environmentally friendly ionic liquid mediated protocol for the synthesis of quinoxaline derivatives using carbonyl substrate and phenylenediamines has been described. A range of ionic liquids were synthesized, characterized via IR, 1H and 13C NMR and used as a solvent as well as catalyst for above protocol. The catalytic activities of ILs were evaluated and the relationship between the catalytic activity and acidity was discussed. It was also found that among the all ILs, [Bmim]CF3SO3 was the most effective, eco-friendly and less expensive solvent and catalyst for the above etiquette. This method is of significant value due to the eco-friendly nature of ionic liquid and non usage of separate catalyst to drive the reaction forward. The protocol proves to be efficient and environmentally benign in terms of good to excellent yields, low reaction times, simple work-up, ease of recovery, and reusability of ionic liquid for six times.

Copper-catalyzed synthesis of valuable heterocyclic compounds using a tandem oxidation process approach

The synthesis of quinoxalines via a tandem oxidation process using a copper acetate monohydrate/2,2,6,6-tetramethylpiperidine N-oxyl (TEMPO) oxidative system has been described. Using this approach, a series of quinoxaline derivatives were formed in good yields within short reaction times under microwave irradiation. The oxidative system was also extended to the selective synthesis of dihydropyrazines and pyrazines.

Ionic liquid 1-butyl-3-methylimidazolium bromide ([bmim]Br): A green and neutral reaction media for the efficient, catalyst-free synthesis of quinoxaline derivatives

Quinoxaline derivatives were produced in excellent yields and short reaction times via the condensation of 1,2-diamines with 1,2-diketones in the neutral ionic liquid 1-butyl-3-methylimidazolium bromide ([bmim]Br) under catalyst-free and microwave irradia

PTSA-catalyzed one-pot synthesis of quinoxalines using DMSO as the oxidant

An efficient p-toluene sulfonic acid–catalyzed, one-pot, two-step oxidative system for cyclization of o-diaminobenzene with 1,2-diaryl-2-hydroxyethanone to quinoxalines was described. A nontoxic, readily available oxidant, dimethylsulfoxide (DMSO), was applied in this process. A broad range of substrates was applied to this method, and target compounds were obtained with good yields.

Silica sulfuric acid (SSA)/polyethylene glycol (PEG) as a recyclable system for the synthesis of quinoxalines and pyrazines

An efficient and facile method has been developed for the condensation of 1,2-diamines with-hydroxyketones in polyethylene glycol (PEG) to quinoxalines and pyrazines with good yields in the presence of silica sulfuric acid (SSA). The important features of the methodology are simple operations, environmentally friendliness, and no requirement for metal catalysts. Additionally, the catalyst system (SSA/PEG) could be recovered easily and reused.

Ruthenium?p-cymene complexes with acylthiourea, and its heterogenized form on graphene oxide act as catalysts for the synthesis of quinoxaline derivatives

Synthesis of a series of half-sandwich Ru(II) complexes (1-5) containing acylthiourea ligand is reported herein. All the Ru(II) complexes were well characterized by analytical and spectroscopic (UV-Vis, FT-IR, NMR and mass spectrometry) methods. Molecular structures of two (2 and 3) of the complexes were confirmed by single crystal X-ray diffraction, and the complexes adopted pseudo-octahedral geometry around Ru. Catalytic ability of the Ru complexes was evaluated in the synthesis of quinoxaline compounds from various 2-nitroaniline and hydroxy ketone derivatives via transfer hydrogenation approach. Active homogeneous catalyst was heterogenized by supporting it on graphene oxide, and the heterogeneous equivalent was characterized by Raman, XPS, TEM, SEM and ICP-OES techniques. Activity of the heterogeneous catalyst was tested, and it can be reused up to five cycles without any loss in activity.

NaOH-Mediated Direct Synthesis of Quinoxalines from o-Nitroanilines and Alcohols via a Hydrogen-Transfer Strategy

A NaOH-mediated sustainable synthesis of functionalized quinoxalines is disclosed via redox condensation of o-nitroamines with diols and α-hydroxy ketones. Under optimized conditions, various o-nitroamines and alcohols are well tolerated to generate the desired products in 44-99% yields without transition metals and external redox additives.

Iron-Catalyzed Hydrogen Transfer Reduction of Nitroarenes with Alcohols: Synthesis of Imines and Aza Heterocycles

A straightforward and selective reduction of nitroarenes with various alcohols was efficiently developed using an iron catalyst via a hydrogen transfer methodology. This protocol led specifically to imines in 30-91% yields, with a good functional group tolerance. Noticeably, starting from o-nitroaniline derivatives, in the presence of alcohols, benzimidazoles can be obtained in 64-72% yields when the reaction was performed with an additional oxidant, DDQ, and quinoxalines were prepared from 1,2-diols in 28-96% yields. This methodology, unprecedented at iron for imines, also provides a sustainable alternative for the preparation of quinoxalines and benzimidazoles.