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Preparation method of 3-alkyl quinoxaline-2(1H)-ketone compound

A technology of ketone compounds and alkylquinones, which is applied in the field of organic synthesis, can solve problems such as unrealized reactions, and achieve the effects of good applicability, reduced reaction costs and energy consumption, and high reaction efficiency

Inactive Publication Date: 2019-08-13
HUNAN UNIV OF SCI & ENG
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Although these reports have enriched the synthetic methods of 3-alkylquinoxalin-2(1H)-ones, the alkylation reactions reported in these reports are limited to relatively special alkyl groups such as oxyalkylation or cyanoalkylation. Alkylation, the general type of alkylation reaction, such as methylation, ethylation, isopropylation, cyclopropylation and some long-chain alkylation reactions with functional groups, the reactions reported so far cannot be realized

Method used

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  • Preparation method of 3-alkyl quinoxaline-2(1H)-ketone compound
  • Preparation method of 3-alkyl quinoxaline-2(1H)-ketone compound
  • Preparation method of 3-alkyl quinoxaline-2(1H)-ketone compound

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Embodiment 1

[0045]

[0046] Add iodobenzene diacetate (10mmol) and propionic acid (20mmol) into a round-bottomed flask, dissolve them in 25ml of chloroform, and concentrate to dryness under reduced pressure at 50°C to obtain iodobenzene dipropionate 2b, which is used directly for Next reaction.

[0047] At 25°C, in a 10mL reaction tube, sequentially add 1-methylquinoxaline-2(1H)-one 1a (0.2mmol), iodobenzene dipropionate 2b (0.44mmol), Ru(bpy) 3 Cl 2 ·6H 2 O (0.002mmol), PEG-200 (1mL), mixed evenly, and then stirred and reacted for 8h under the irradiation of 3w blue LED light. After the reaction was detected by TLC, cyclopentyl methyl ether (2ml×3) was added for extraction, and the upper layer extract was taken and concentrated in vacuum at 50°C until there was no solvent to obtain a crude product, which was then extracted with petroleum ether at a volume ratio of 2:1 Wash with ethyl acetate mixed eluent, flash column chromatography on silica gel to obtain 3-ethyl-1-methylquinoxali...

Embodiment 2

[0050]

[0051] Add iodobenzene diacetate (10mmol) and cyclohexanecarboxylic acid (20mmol) in a round bottom flask, dissolve in 25ml of chloroform, and concentrate to dryness under reduced pressure at 50°C to obtain iodobenzene dicyclohexanecarboxylate 2c without purification , used directly in the next reaction.

[0052] At 25°C, in a 10mL reaction tube, sequentially add 1-methylquinoxaline-2(1H)-one 1a (0.2mmol), iodobenzene dicyclohexanecarboxylate 2c (0.44mmol), Ru(bpy) 3 Cl 2 ·6H 2 O (0.002mmol), PEG-200 (1mL), mixed evenly, and then stirred and reacted for 6h under the irradiation of 3w blue LED light. After the reaction was detected by TLC, cyclopentyl methyl ether (2ml×3) was added for extraction, and the upper layer extract was taken and concentrated in vacuum at 50°C until there was no solvent to obtain a crude product, which was then extracted with petroleum ether at a volume ratio of 2:1 Wash with ethyl acetate mixed eluent, silica gel column flash column chr...

Embodiment 3

[0055]

[0056] Add iodobenzene diacetate (10mmol) and n-octanoic acid (20mmol) into a round-bottomed flask, dissolve them in 25ml of chloroform, and concentrate to dryness under reduced pressure at 50°C to obtain iodobenzene dioctanoate 2d, which is directly used in the next step without purification. One step reaction.

[0057] At 25°C, in a 10mL reaction tube, sequentially add 1-methylquinoxaline-2(1H)-one 1a (0.2mmol), iodobenzene dioctanoate 2d (0.44mmol), Ru(bpy) 3 Cl 2 ·6H 2 O (0.002mmol), PEG-200 (1mL), mixed evenly, and then stirred and reacted for 8h under the irradiation of 3w blue LED light. After the reaction was detected by TLC, cyclopentyl methyl ether (2ml×3) was added for extraction, and the upper layer extract was taken and concentrated in vacuum at 50°C until there was no solvent to obtain a crude product, which was then extracted with petroleum ether at a volume ratio of 2:1 Wash with ethyl acetate mixed eluent, silica gel column flash column chromato...

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Abstract

The invention discloses a preparation method of a 3-alkyl quinoxaline-2(1H)-ketone compound. According to the method, aliphatic carboxylic acid reacts with iodobenzene diacetate to obtain dialiphaticcarboxylic acid iodobenzene, and the dialiphatic carboxylic acid iodobenzene and a quinoxaline ketone compound are subjected to a visible-light catalytic reaction under the action of a photocatalyst to obtain the 3-alkyl quinoxaline ketone compound. Compared with the prior art, the synthesis method has the advantages that the raw materials such as a quinoxaline-2(1H)-ketone derivative and fatty acid in use are cheap and easy to obtain, so that the cost is reduced; lighting can be carried out at room temperature, conditions are mild, the product is obtained in one step, the reaction yield is high, the operation is environmentally friendly, and industrial production is facilitated; the method is good in functional group applicability and can obtain various 3-alkyl quinoxaline-ketone compoundderivatives, and a brand-new synthetic path is provided for the 3-alkyl quinoxaline-2(1H)-ketone compound.

Description

technical field [0001] The present invention relates to a kind of synthetic method of quinoxalinone derivatives, particularly relate to taking quinoxalin-2(1H)-ketone compound as starting material, under the action of dialiphatic carboxylic acid iodobenzene and photocatalyst, The invention discloses a method for preparing 3-alkylquinoxalin-2(1H)-one through visible light catalysis, belonging to the technical field of organic synthesis. Background technique [0002] Nitrogen heterocyclic derivatives are important constituents of active natural products and synthetic drugs. Compounds containing this core structure are widely used in medicine, pesticides, and industrial dyes. They are a class of compounds with a wide range of potential uses. As an important class of nitrogen heterocyclic derivatives, quinoxaline-2(1H)-ones have been widely used in natural products, pharmacy and materials science, among which 3-alkylquinoxaline-2(1H )-Kone derivatives have attracted the interes...

Claims

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Application Information

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IPC IPC(8): C07D241/44
CPCC07D241/44
Inventor 谢龙勇蒋丽林谭家希包文虎刘开建
Owner HUNAN UNIV OF SCI & ENG
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