Synthesis method of C-3-position difluoromethyl-substituted quinoxalinone derivative

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 present invention relates to a method for synthesizing C-3 difluoromethyl substituted quinoxalinone derivatives. Background technique [0002] The structure of quinoxalinone is a commonly used pharmacophore in the field of drug design. Studies have confirmed that the derivatives containing the nucleus 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, which mainly include: (1) the introduction of an aromatic ring at the C-3 position of quinoxalinone (K. Yin, RH Zhang, Org. Lett . 2017, 19 , 1530; J. W. Yuan, S. N. Liu, L. B. Qu, Adv. Synth. Catal . 2017, 359 , 4197); (2) The introduction of amino groups at the C-3 position of quino...

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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

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