A kind of synthetic method of c-3 difluoromethyl substituted quinoxalinone derivatives

A kind of quinoxalinone and difluoromethyl technology, which is applied in the field of synthesis of C-3-position difluoromethyl substituted quinoxalinone derivatives, can solve problems such as harsh conditions, and achieve reaction safety and reaction selectivity. Good, rich effect of synthetic methods

Active Publication Date: 2020-10-09
ZHEJIANG UNIV OF TECH
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AI Technical Summary

Problems solved by technology

Although the introduction of fluorine-containing groups at the C-3 position of quinoxalinones has been achieved through oxidative decarboxylation coupling or the catalysis of metal copper complexes (G. F. Hong, J. W. Yuan, J. H. Fu, G. Y. Pan, Z. W. Wang, L. R. Yang, Y. M. Xiao, P. Mao, X. M. Zhang, Org. Chem. Front. 2019, 6 , 1173; L. P. Wang, H. Y. Liu, F. F. Li, J. Q. Zhao, H. Y. Zhang, Y. C. Zhang, Adv. Synth. Catal. 2019, 361 , 2354), but the existing methods still have defects such as harsh conditions and excessive oxidant participation

Method used

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  • A kind of synthetic method of c-3 difluoromethyl substituted quinoxalinone derivatives
  • A kind of synthetic method of c-3 difluoromethyl substituted quinoxalinone derivatives

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Experimental program
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Embodiment 1

[0024] 1-Methylquinoxalinone (0.25 mmol, 40 mg), ethyl bromodifluoromethyl acetate (0.5 mmol, 101 mg), Ir(ppy) 3 (1.25 μmol, 0.8 mg), potassium carbonate (0.5 mmol, 69 mg) and N,N -Diisopropylethylamine (0.025 mmol, 3.2 mg) was added to a 10 mL solvent storage bottle, and MeCN (1.0 mL) was added as a solvent, under N 2 Under the protection of the atmosphere, the reaction was carried out under 3 w blue light irradiation at 25 °C for 12 h. After the reaction, the reaction system was washed with water and extracted with dichloromethane, then separated into an organic layer and an aqueous layer. After the organic layer was dried with anhydrous sodium sulfate, it was evaporated and concentrated under reduced pressure to remove the solvent to obtain a yellow oil. The yellow oil was separated by column chromatography, using a mixture of petroleum ether and ethyl acetate with a volume ratio of 30:1 as the eluent, collecting the eluate containing the target compound, distilling off t...

Embodiment 2

[0027] The inorganic base (potassium carbonate) in the system was replaced with sodium carbonate (0.5 mmol, 52.9 mg), and other operations were the same as in Example 1 to obtain 46 mg of white solid 2,2-difluoro-2-(4-methyl-3 -Oxo-3,4-dihydroquinoxalin-2-yl)-ethyl acetate, yield 65%.

Embodiment 3

[0029] Will N,N - The amount of diisopropylethylamine was changed to 0.05 mmol, and other operations were the same as in Example 1 to obtain 44 mg of white solid 2,2-difluoro-2-(4-methyl-3-oxo-3,4- Dihydroquinoxalin-2-yl)-ethyl acetate, yield 62%.

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Abstract

The invention discloses a synthesis method of a C-3-position difluoromethyl-substituted quinoxalinone derivative. The method comprises the steps of dissolving a quinoxalinone derivative, a bromodifluoromethyl compound, a photocatalyst, an inorganic base and an organic amine in an organic solvent for a reaction for 6-36 hours at the temperature of 20-60 DEG C under the irradiation of visible light;after the reaction is finished, carrying out posttreatment on a reaction system to obtain a target product, namely the C-3-position difluoromethyl-substituted quinoxalinone derivative. According to the method, light is adopted as a reaction energy source to realize C-3 difluoro methylation of quinoxalinone, so that the reaction is safer, environmentally friendly and lower in cost, the applicationrange of reaction substrates is expanded, and synthesis methods of C-3 substituted quinoxalinone compounds are diversified.

Description

technical field [0001] The invention relates to a synthesis method of C-3 difluoromethyl substituted quinoxalinone derivatives. Background technique [0002] The quinoxalinone structure is a commonly used pharmacophore in the field of drug design. Studies have confirmed that derivatives containing the core of this structure have a variety of pharmacological activities, including anti-tumor, anti-(true) bacteria, anti-coagulation, etc. As potential lead compounds, quinoxalinone structures have broad research prospects in the field of new drug development. In recent years, some progress has been made in the synthesis of quinoxalinone derivatives substituted at the C-3 position, mainly including: (1) the introduction of an aromatic ring at the C-3 position of quinoxalinones by metal or metal-free catalysis (K. Yin, R. H. Zhang, Org. Lett . 2017, 19 , 1530; J. W. Yuan, S. N. Liu, L. B. Qu, Adv. Synth. Catal . 2017, 359 , 4197); (2) The amino group was introduced at the C-3...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D241/44
CPCC07D241/44
Inventor 金灿孙彬庄小慧
Owner ZHEJIANG UNIV OF TECH
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