154640-54-7

Upstream product

• 1235982-73-6 ethyl (2-oxo-3,4-dihydroquinoxalin-1(2H)-yl)acetate 
• 1196-57-2 quinoxalin-2⁽¹⁾-one 
• 95-54-5 1,2-diamino-benzene 
• 1196-57-2 2-hydroxyquinoxaline 
• 105-36-2 ethyl bromoacetate 

Relevant academic research and scientific papers

Metal-free C3-H acylation of quinoxalin-2(1: H)-ones with α-oxo-carboxylic acids

Direct C3-H acylation of quinoxalin-2(1H)-ones with α-oxocarboxylic acids under thermo conditions promoted by PIDA has been achieved in a moderate to good yield in a very fast manner. Mechanistic study revealed that the reaction proceeds via a radical pro

Photoinduced ligand to metal charge transfer enabling cerium mediated decarboxylative alkylation of quinoxalin-2(1H)-ones

Here, we report the cerium-mediated decarboxylative alkylation of quinoxalin-2(1H)-ones utilizing feedstock carboxylic acids as a radical precursor via photoinduced-LMCT. This operationally simple protocol overcomes the limitation of the direct use of carboxylic acids to access alkyl radicals. Spectroscopic investigations reveal the photoinduced LMCT and CO2 evolving events. We have utilized a broad range of alkyl carboxylic acids (1° to 3° acids), amino acids and pharmaceutically-important acids as a coupling partner to synthesise the desired alkylated heterocyclic product in good to excellent yields.

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.

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.

Direct functionalization of quinoxalin-2(1H)-one with alkanes: C(sp2)-H/C(sp3)-H cross coupling in transition metal-free mode

Considering the significance of pharmaceutically important heterocycles, efficient and highly versatile protocols for the functionalization of diverse heterocycles with easily accessible feedstock are crucial. Here, we have reported selective alkylation of quinoxalin-2(1H)-one with a broad class of hydrocarbons having different C(sp3)-H bonds with varying bond strengths using di-tert-butyl peroxide (DTBP) as an alkoxyl radical mediator for hydrogen atom transfer (HAT). This dehydrogenative coupling approach utilizes feedstock chemicals such as cycloalkanes, cyclic ethers and alkyl arenes as coupling partners. This protocol exhibits good functional group compatibility and selectivity regarding both heterocycles and unactivated alkanes. Moreover, this methodology allows functionalization of relatively strong C-H bonds of adamantane and exclusive selectivity towards 3° C(sp3)-H bonds is observed. We also illustrate the applicability of this C(sp2)-H/C(sp3)-H cross-coupling for practical access to bioactive pharmaceuticals.

Electro-oxidative C-H azolation of quinoxalin-2(1H)-ones

We have developed a practical, general protocol for direct C-H azolation reactions of quinoxalin-2(1H)-ones by electro-oxidative cross-coupling. These mild reactions proceed under metal-, oxidant-, and reagent-free conditions to provide synthetically useful azolated quinoxalin-2(1H)-ones. Furthermore, the reactions can be carried out with a pencil lead as an electrode and a 3 V battery as a power source, revealing the remarkable flexibility of this protocol.

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.

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.

Electrochemical chlorination and bromination of electron-deficient C[sbnd]H bonds in quinones, coumarins, quinoxalines and 1,3-diketones

The electrochemistry-promoted chlorination and bromination of electron-deficient C[sbnd]H bonds was developed, using quinones, coumarins, quinoxalines and 1,3-diketones. This protocol features readily available and safe halogen sources (hydrochloric acid and KBr), high site-selectivity and mild reaction conditions. It could provide an efficient access to a series of chlorinated and brominated quinones, coumarins, quinoxalines and 1,3-diketones.