A kind of synthetic method of C-3 alkyl-substituted quinoxalinone derivatives based on minisci reaction

Abstract

The invention discloses a synthesis method of C-3 alkyl substituted quinoxalinone derivatives based on the Minisci reaction. 2 Under protective atmosphere and visible light irradiation, as the quinoxalinone derivative shown in formula (I), the quinoxalinone derivative shown in formula (II) N ‑Alkanoyloxyphthalimide compounds, photocatalysts and additives are added into an organic solvent for reaction. After the reaction, the reaction liquid system is post-treated to obtain the C‑3 alkyl group represented by formula (III). Substituted quinoxalinone derivatives; the reaction formula is as follows: In formula (I) and formula (III), substituent R 1 Is H, C1‑C3 alkyl, benzyl or propargyl; substituent R 2 Is H, methoxy, fluorine, chlorine, bromine or trifluoromethyl; in formula (II) and formula (III), substituent R 3 It is one of C1-C8 linear or branched chain alkyl, C5-C6 cycloalkyl, and C3-C5 alkenyl. The invention uses visible light as the energy source of 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, which can reduce the production cost.

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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