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A kind of photocatalytic synthesis method of 3-aryl-n-methylquinoxalin-2(1h)-one compound

A technique for aryl formyl peroxide and methylquinoxaline is applied in the field of photocatalytic synthesis of 3-aryl-N-methylquinoxaline-2(1H)-one compounds, which can solve the problem of yield Low, difficult to obtain phase transfer catalyst, long reaction time and other problems, to achieve the effect of high yield, good compatibility and high reaction selectivity

Active Publication Date: 2021-12-31
HUNAN UNIV OF SCI & ENG
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Taking the latest reported synthesis method as an example, such as (Chem-Eur.J., 2020, 26, 369-373) discloses a method using arylhydrazine as an aryl source, under the action of a special phase transfer catalyst 2D-COF-1 , undergoes a free radical reaction mechanism through blue light irradiation, and arylhydrazine replaces the C-H on the quinoxalin-2(1H)-one compound C3 through dehydration, as shown in the following reaction formula 1. The 2D-COF-1 used in this method Phase transfer catalysts are not easy to obtain, and the reaction time is long and the yield is low
Another example (RSC Adv., 2020, 10, 3615-3624) discloses that phenylhydrazine is used as an aryl source, and under the oxidation of potassium persulfate, it undergoes a free radical reaction mechanism under heating conditions to perform dehydration to replace quinoxa The C-H on the lin-2(1H)-one compound C3 is shown in the following reaction formula 2. This method needs to be reacted under heating conditions, and the reaction time is long and the yield is low

Method used

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  • A kind of photocatalytic synthesis method of 3-aryl-n-methylquinoxalin-2(1h)-one compound
  • A kind of photocatalytic synthesis method of 3-aryl-n-methylquinoxalin-2(1h)-one compound
  • A kind of photocatalytic synthesis method of 3-aryl-n-methylquinoxalin-2(1h)-one compound

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Embodiment 1～5

[0043] The following examples 1 to 5 all react according to the following reaction equation, mainly to investigate the yield situation of different substrates reacting under optimal conditions:

[0044]

[0045] The specific operation steps are: in a 10mL quartz reaction tube, sequentially add N-methylquinoxaline-2(1H)-one (0.3mmol), aryl peroxide (0.45mmol) and EtOAc (1.5mL) , The resulting mixed solution is irradiated with visible light with a wavelength of 415-420nm at a light source power of 6W. TLC plate was used to track the reaction progress, and the reaction time was 3 hours. After the reaction, the extract was concentrated by a rotary evaporator, and purified by column chromatography using petroleum ether / ethyl acetate as eluent.

Embodiment 1

[0047] Compound 1, yield 88%, 1-methyl-3-phenylquinoxalin-2(1H)-one;

[0048]

[0049] 1 H NMR (400MHz, CDCl 3 ):δ=8.32–8.30(m,2H),7.94(dd,J 1 =8.0Hz,J 2 =2.0 Hz,1H),7.59–7.54(m,1H),7.49–7.47(m,3H),7.39–7.32(m,2H),3.77(s,3H);

[0050] 13 C NMR (100MHz, CDCl 3 ): δ=154.7, 154.1, 136.0, 133.3, 133.1, 130.4, 130.3, 129.5, 128.0, 123.7, 113.5, 29.3.

Embodiment 2

[0052] Compound 2, yield 75%, 1-methyl-3-(p-tolyl)quinoxalin-2(1H)-one;

[0053]

[0054] 1 H NMR (400MHz, CDCl 3 ): δ=8.25(d, J=8.0Hz, 2H), 7.92(dd, J 1 =8.0Hz,J 2 =1.6Hz,1H),7.56–7.51(m,1H),7.37–7.28(m,4H),3.75(s,3H),2.42(s,3H);

[0055] 13 C NMR (100MHz, CDCl 3 ): δ=154.7, 153.9, 140.6, 133.3, 133.2, 133.1, 130.3, 130.0, 129.5, 128.8, 123.6, 113.5, 29.2, 21.5.

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Abstract

The invention discloses a photocatalytic synthesis method of a 3-aryl-N-methylquinoxaline-2(1H)-ketone compound. The method is to synthesize N-methylquinoxaline under the condition of 415-420nm purple light irradiation Line-2(1H)-one compound and aryl formyl peroxide react in one pot in ethyl acetate solution to generate 3-aryl-N-methylquinoxaline-2(1H)-one compound; the The method has the advantages of mild conditions, simple operation, environmental protection, easy access to raw materials, excellent compatibility of substrate functional groups, and high reaction yield.

Description

technical field [0001] The present invention relates to a photocatalytic synthesis method of 3-aryl-N-methylquinoxalin-2(1H)-one compound, in particular to a kind of aryl formyl peroxide compound as aryl source, The invention discloses a method for directly decarboxylating and substituting C-3 hydrogen under irradiation conditions, and highly selectively synthesizing 3-aryl-N-methylquinoxalin-2(1H)-one compounds, belonging to the technical field of organic intermediate synthesis. Background technique [0002] Quinoxaline-2(1H)-one compound is a commonly used pharmacophore in the field of drug research. The derivatives of the parent structure have a variety of physiological and pharmacological activities, and are widely used as anticancer drugs, antitumor drugs, antibacterial drugs, etc. , is a class of potential multi-purpose lead compounds with broad development and application prospects. In fact, quinoxalinone and the modified functional groups on the quinoxalinone parent...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D241/44
CPCC07D241/44
Inventor 何卫民谢龙勇彭莎杨丽华
Owner HUNAN UNIV OF SCI & ENG