49568-76-5

Upstream product

• 124831-91-0 3-(α-chlorobenzyl)-1,2-dihydroxyquinoxalin-2-one 
• 289704-35-4 2-oxo-3-(α-thiocyanobenzyl)-1,2-dihydroquinoxaline 
• 24949-43-7 3-benzylquinoxalin-2-one 
• 16439-95-5 4-phenyl-2,3-dihydro-1H-1,5-benzodiazepin-2-one 
• 1196-57-2 quinoxalin-2⁽¹⁾-one 
• 6125-26-4 phenyl(2-phenyl-2,3-dihydrobenzo[d]thiazol-2-yl)methanone 
• 6323-89-3 3-[2-phenylethenyl]quinoxalin-2(1H)-one 
• 100-52-7 benzaldehyde 
• 611-73-4 Benzoylformic acid 
• 156-06-9 2-oxo-3-(phenyl)propionic acid 
• 95-54-5 1,2-diamino-benzene 
• 6476-17-1 ethyl 3-bromo-2-oxo-3-phenylpropionate 
• 881-90-3 4-benzylidene-2-methyl-2-oxazolin-5-one 
• 24949-43-7 3-benzylquinoxalin-2-ol 

Downstream Products

• 14428-35-4 1,3-diphenyl-1H-pyrazolo<3,4-b>quinoxaline 
• 109002-28-0 3-phenyl-1-(p-tolyl)-1H-pyrazolo<3,4-b>quinoxaline 
• 92868-25-2 1-methyl-3-benzoylquinoxalin-2(1H)-one 
• 1322668-82-5 2-[2-(4-nitrophenyl)-5-phenylimidazol-4-yl]benzimidazole 

Relevant academic research and scientific papers

The kornblum reaction of α-substituted 3-benzyl-1,2-dihydro-2-oxoquinoxalines. Synthesis and structure of 3-benzoyl-2-oxo-1,2-dihydroquinoxaline

A method has been developed for the preparation of 3-benzoyl-2-oxo-1,2-dihydroquinoxaline by the reaction of 3-(α-chlorobenzyl)-1,2-dihydroquinoxaline under Kornblum reaction conditions to the corresponding α-azido derivative and then acid fission of the latter. The structure of the target ketone has been confirmed by x-ray analysis.

Metal-free oxidative coupling of quinoxalin-2(1: H)-ones with arylaldehydes leading to 3-acylated quinoxalin-2(1 H)-ones

A facile TBHP-mediated direct oxidative coupling of quinoxalin-2(1H)-ones with arylaldehydes has been developed under metal-free conditions. This method provided a convenient and efficient approach to various 3-acylated quinoxalin-2(1H)-ones from readily available starting materials with excellent regioselectivity. This reaction proceeded efficiently under mild conditions over a broad range of substrates and with functional group tolerance.

Oxidative dehydrobromination of 3-(α-bromobenzyl)quinoxalin-2(1H)- ones according to Kornblum as a simple and efficient synthetic route to quinoxalyl aryl ketones

Condensation of ethyl 3-aryl-3-bromo-2-oxopropanoates with o-phenylenediamine in acetic acid gave 3-(α-bromobenzyl)quinoxalin-2(1H)- ones which were converted in high yield into the corresponding 3-aroylquinoxalin-2(1H)-ones via oxidative dehydrobrominati

Direct photoexcitation of benzothiazolines: Acyl radical generation and application to access heterocycles

An acyl radical generation and functionalization strategy through direct photoexcitation of benzothiazolines has been developed. The formed acyl radical species can either be trapped by quinoxalin-2-ones to realize their C(3)-H functionalization or trigger a cascade radical cyclization with isonitriles to synthesise biologically important phenanthridines. The synthetic value of this protocol can be further illustrated by the modification of quinoxalin-2-ones, containing important natural products and drug-based complex molecules.

Intramolecular oxidative rearrangement: I2/TBHP/DMSO-mediated metal free facile access to quinoxalinone derivatives

Iodine/TBHP/DMSO mediated oxidative rearrangement of 3-styrylquinoxalin-2(1H)-one led to the formation of 3-aroylquinoxalin-2(1H)-ones in good to high yields via Kornblum oxidation. This methodology proceeds under mild conditions via oxidative aryl migrat

Eosin Y as a direct hydrogen-atom transfer photocatalyst for the C3-H acylation of quinoxalin-2(1H)-ones

Visible light promoted eosin Y catalyzed selective C3-H acylation of quinoxalin-2(1H)-ones has been developed in a green and sustainable manner. In contrast to the conventional anionic eosin Y-based photoredox process, neutral eosin Y acts as the actual c

Activated carbon/Br?nsted acid-promoted aerobic benzylic oxidation under “on-water” condition: Green and efficient synthesis of 3-benzoylquinoxalinones as potent tubulin inhibitors

Green chemistry is becoming the favored approach to preparing drug molecules in pharmaceutical industry. Herein, we developed a clean and efficient method to synthesize 3-benzoylquinoxalines via activated carbon promoted aerobic benzylic oxidation under “on-water” condition. Moreover, biological studies with this class of compounds reveal an antiproliferative profile. Further structure modifications are performed and the investigations exhibited that the most active 12a could inhibit the microtubule polymerization by binding to tubulin and thus induce multipolar mitosis, G2/M phase arrest, and apoptosis of cancer cells. In addition, molecular docking studies allow the rationalization of the pharmacodynamic properties observed. Our systematic studies provide not only guidance for applications of O2/AC/H2O system, but also a new scaffold targeting tubulin for antitumor agent discovery.

Preparation method 3 -acyl quinoxalinone derivatives

The invention discloses a method for preparing a 3-acyl quinoxaline ketone derivative (I) and belongs to the field of organic chemistry The method comprises the following steps: by taking a substituted quinoxaline-2-ketone derivative and aldehyde or benzyl alcohol as raw materials, and a 70% tert-butyl hydroperoxide (TBHP) solution as an oxidant, performing a heating reaction in a solvent withoutmetal catalysis, thereby synthesizing the 3-acyl quinoxaline ketone derivative. Compared with a conventional synthesis method, the method has the advantages that firstly, the raw materials are cheap and easy to obtain, the 3-acyl quinoxaline ketone derivative is synthesized at one step, the cost is low, and good application prospects can be achieved; secondly, the method is gentle in reaction condition, high in yield, convenient to operate, beneficial to industrial production and the like, and the reactions are carried out under an air condition. The derivative has potential application in fields such as medicines, chemical engineering and materials, and the invention provides a novel way for synthesis of 3-acyl quinoxaline ketone derivatives. (Refer to Specification).

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

Photoredox Catalyst Free, Visible Light-Promoted C3?H Acylation of Quinoxalin-2(1H)-ones in Water

A method for the synthesis of 3-acyl quinoxalin-2(1H)-ones through visible-light promoted decarboxylative acylation of α-oxo-carboxylic acids with quinoxalin-2(1H)-ones was developed. The reaction was performed in aqueous phase and photoredox catalyst was not required to run the process. (Figure presented.).