Synthetic method for C-3 position alkyl-substituted quinoxalinone derivatives based on Minisci reaction

Abstract

The invention discloses a synthetic method for C-3 position alkyl-substituted quinoxalinone derivatives. The method comprises the following steps: under a N2 protective atmosphere and visible light irradiation, adding one quinoxalinone derivative represented by a formula (I), one N-alkylcarbonyloxyphthalimide compound represented by a formula (II), a photocatalyst and an additive into an organic solvent, performing a reaction, and after the reaction is completed, performing post-treatment on the reaction liquid system to obtain one C-3 position alkyl-substituted quinoxalinone derivative represented by a formula (III), wherein a reaction formula is shown in the description, in the formula (I) and (III), the substituent group R<1> is one selected from the group consisting of H, C1-C3 alkyl,benzyl and propargyl, and the substituent group R<2> is one selected from the group consisting of H, methoxy, fluoro, chloro, bromo and trifluoromethyl; and in the formula (II) and (III), the substituent group R<3> is one selected from the group consisting of C1-C8 linear or branched alkyl, C5-C6 cycloalkyl and a C3-C5 alkenyl. The method provided by the invention uses visible light as an energy source for the reaction, so that the reaction conditions are milder, and the production operation is safer; and the substrate of the reaction is cheap and easy to obtain, so that the production costs can be reduced.

Description

technical field [0001] The invention relates to a synthesis method of C-3 alkyl-substituted quinoxalinone derivatives based on Minisci reaction. Background technique [0002] Quinoxalinone derivatives are structural nuclei found in natural compounds that play an important role. Studies have shown that quinoxalinone derivatives, especially C-3 alkyl substituted quinoxalinone derivatives, have good biological activity. It is mainly used as an inhibitor of various enzymes in the human body. In addition, quinoxalinone derivatives play an important role in the field of organic synthesis and materials. [0003] The synthesis of C-3 alkyl-substituted quinoxalinone mainly has the following methods: (1) through the coupling of 1,2-phenylenediamine and α, β-diketone ester; (2) using metal copper to catalyze Realize the benzylation of the C-3 position of quinoxalinone; (3) use TBHP as an oxidant without metal catalysts, introduce ether or cycloalkane at the C-3 position of quinoxali...

AI Technical Summary

Problems solved by technology

The above methods often require the participation of metal catalysts and excessive oxidants, which increases the emission of toxic and harmful substances

In addition, these methods require a higher reaction temperature, which not only increases the consumption of energy, but also reduces the safety of production.

In addition, the limited range of substrates also greatly limits the application of these methods

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