63536-44-7

Upstream product

• 1196-57-2 quinoxalin-2⁽¹⁾-one 
• 1196-57-2 2-hydroxyquinoxaline 
• 100-39-0 benzyl bromide 
• 14003-34-0 3-methyl-2-oxo-1,2-dihydroquinoxaline 
• 100-44-7 benzyl chloride 
• 59564-59-9 1,2,3,4-tetrahydroquinoxalin-2-one 
• 5428-05-7 n-(2-nitrophenyl)glycine ethyl ester 
• 1493-27-2 ortho-nitrofluorobenzene 
• 100-46-9 benzylamine 
• 95-54-5 1,2-diamino-benzene 
• 1239573-83-1 N-benzyl-2-chloro-N-(2-bromophenyl)acetamide 
• 1239573-73-9 N-benzyl-2-chloro-N-(2-iodophenyl)-acetamide 
• 2564-06-9 N-benzyl-2-chloroacetamide 
• 116547-92-3 N-(2-iodophenyl)methanesulfonamide 

Downstream Products

• 1196-57-2 quinoxalin-2⁽¹⁾-one 
• 84546-74-7 3-methyl-1-benzylquinoxaline-2(1H)-one 

Relevant academic research and scientific papers

Electro-reductive C-H cyanoalkylation of quinoxalin-2(1H)-ones

Herein, we report a practical electro-reductive protocol for the direct C–H cyanoalkylation of quinoxalin-2(1H)-ones via iminyl radical-mediated ring opening. These mild reactions proceed under metal-, reductant-, and reagent-free conditions to provide synthetically useful cyanoalkylated quinoxalin-2(1H)-ones.

Photoinitiated Multicomponent Anti-Markovnikov Alkoxylation over Graphene Oxide

The development of graphene oxide–based heterogeneous materials with an economical and environmentally–friendly manner has the potential to facilitate many important organic transformations but proves to have few relevant reported reactions. Herein, we explore the synergistic role of catalytic systems driven by graphene oxide and visible light that form nucleophilic alkoxyl radical intermediates, which enable an anti-Markovnikov addition exclusively to the terminal alkenes, and then the produced benzyl radicals are subsequently added with N–methylquinoxalones. This photoinduced cascade radical difunctionalization of olefins offers a concise and applicable protocol for constructing alkoxyl–substituted N–methylquinoxalones.

Method for catalytically preparing 3-sulfur substituted quinoxalinone derivative

The invention relates to a method for catalytically preparing a 3-sulfur substituted quinoxalinone derivative. The method comprises the following steps of: firstly preparing a 3-(thiophenyl) quinoxaline-2 (1H)-ketone derivative, then adding the 3-(thiophenyl) quinoxaline-2 (1H)-ketone derivative, disulfide, an oxidizing agent and a catalyst into a reaction container, adding a solvent, reacting under the light irradiation of a blue lamp, and after the reaction is completed, filtering, extracting, concentrating, separating and purifying to obtain the 3-sulfur substituted quinoxalinone derivative. According to the invention, the problem that a traditional catalyst needs high-temperature reaction is solved, disulfide is used as a raw material, the problem that foul thiophenol and thiol substances are used as raw materials traditionally is solved, and a green and efficient synthesis method is used to promote industrialization of a reaction system; and meanwhile, quinoxalinone compounds with different substituent groups are also efficiently expanded.

N, N, N', N'-Tetramethylethylenediamine-Enabled Photoredox-Catalyzed C-H Methylation of N-Heteroarenes

Aiming at the valuable methylation process, readily available and inexpensive N,N,N′,N′-tetramethylethylenediamine (TMEDA) was first identified as a new methyl source in photoredox-catalyzed transformation in this work. By virtue of this simple methylating reagent, a facile and practical protocol for the direct C-H methylation of N-heteroarenes was developed, featuring mild reaction conditions, broad substrate scope, and scalability. Mechanistic studies disclosed that a sequential photoredox, base-assisted proton shift, fragmentation, and tautomerization process was essentially involved.

Light-driven selective aerobic oxidation of (iso)quinoliniums and related heterocycles

Selective C1-H/C4-H carbonylation of N-methylene iminium salts, catalyzed by visible-light photoredox and oxygen in the air, has been reported. A ruthenium complex acts as a chemical switch to conduct two different reaction pathways and to afford two diff

C?H Methylation of Iminoamido Heterocycles with Sulfur Ylides**

The direct methylation of N-heterocycles is an important transformation for the advancement of pharmaceuticals, agrochemicals, functional materials, and other chemical entities. Herein, the unprecedented C(sp2)-H methylation of iminoamido heterocycles as nucleoside base analogues is described. Notably, trimethylsulfoxonium salt was employed as a methylating agent under aqueous conditions. A wide substrate scope and excellent level of functional-group tolerance were attained. Moreover, this method can be readily applied to the site-selective methylation of azauracil nucleosides. The feasibility of gram-scale reactions and various transformations of the products highlight the synthetic potential of the developed method. Combined deuterium-labeling experiments aided the elucidation of a plausible reaction mechanism.

Visible-Light-Promoted Switchable Synthesis of C-3-Functionalized Quinoxalin-2(1H)-ones

A visible-light-promoted synthesis of quinoxalin-2(1H)-ones has been developed using 9-mesityl-10-methylacridinium perchlorate as an organo-photocatalyst. The atmosphere-controlled method (Ar/air) enabled the selective synthesis of hydroxyl- and acyl-containing quinoxalin-2(1H)-ones under mild reaction conditions without the use of any metal catalysts or toxic reagents. A fluorescent labelling experiment showed that hydroxyl-containing quinoxalin-2(1H)-ones may have utility in various biological applications as potent fluorophores. (Figure presented.).

Simple and green synthesis of benzimidazoles and pyrrolo[1,2-: A] quinoxalines via Mamedov heterocycle rearrangement

A method for the synthesis of coupling compounds of benzimidazoles and pyrrolo[1,2-a]quinoxalines via Mamedov Heterocycle Rearrangement is reported here. This method was conducted at room temperature and only solvent (HOAc) was required. A series of 4-(1H-benzo[d]imidazol-2-yl)pyrrolo[1,2-a]quinoxaline derivatives were obtained in moderate to good yields.

Metal-Free Direct Oxidative C?N Bond Coupling of Quinoxalin-2(1H)-ones with Azoles under Mild Conditions

Direct C3?H amination of quinoxalin-2(1H)-ones with azoles under mild conditions promoted by PIFA has been achieved in good yield in a very fast manner. Mechanistic study revealed that the reaction proceeds through a radical process. In addition, this method could be applied to gram-scale reaction.

K2S2O8-catalyzed highly regioselective amidoalkylation of diverse N-heteroaromatics in water under visible light irradiation

A K2S2O8-catalyzed versatile C(sp2)-C(sp3) bond formation with N-heteroaromatics and γ-lactams/amides was developed. Quinoxalin-2(1H)-one, quinoline, isoquinoline, phthalazine, and benzothiazole reacted with γ-lactams/amides to give the corresponding C(sp2)-H amidoalkylation products in moderate to good yields with high regioselectivity. This visible-light-induced photocatalyst-free reaction was conducted in H2O at ambient temperature, which comply with the principles of "green chemistry". The new K2S2O8 catalytic mechanism was investigated with control experiments.