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

A quinoxalinone and synthesis method technology, which is applied in the field of synthesis of C-3 alkyl substituted quinoxalinone derivatives, can solve the problems of increasing the emission of toxic and harmful substances, increasing energy consumption, high reaction temperature, etc., and achieving Reduce waste discharge, save resources, and have good reaction selectivity

Active Publication Date: 2019-11-12
ZHEJIANG UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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

Method used

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

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0029] Add N-methylquinoxalinone (1.0mmol, 160mg), N-(2,2-dimethyl)propionyloxyphthalimide (1.2mmol, 296mg), trifluoroacetic acid (0.5mmol, 57mg), Na 2 -eosin Y (0.01mmol, 7mg), DMSO (3.0mL), reaction system with N 2 Protected and reacted at room temperature for 40h under 3W white light irradiation. After the reaction is finished, the reaction solution is washed with water and extracted with dichloromethane, and then separated to obtain an aqueous layer and an organic layer. The organic layer is dried with anhydrous sodium sulfate, and the filter residue is removed by filtration. Separation, using a mixed solvent of petroleum ether and ethyl acetate with a volume ratio of 15:1 as an eluent, collecting the eluate containing the target compound, evaporating the solvent and drying to obtain the target product N-methyl-3-tert-butyl Quinoxalinone (white solid) 209mg, yield is 97%, its chemical structural formula is:

[0030] Characterization data: white solid, melting point: 6...

Embodiment 2

[0032] The photocatalyst (Na 2 -eosin Y) is replaced by RoseBengal of equivalent molar amount, other operation is the same as embodiment 1, the quality that obtains target product N-methyl-3-tert-butylquinoxalinone (white solid) is 108mg, and its yield is 50 %.

Embodiment 3

[0034] Replace the white light source in the system with green light or blue light of the same power, other operations are the same as in Example 1, and the quality of the target product N-methyl-3-tert-butylquinoxalinone (white solid) is 162mg and 106mg, the yields were 75% and 49%.

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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...

Claims

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Application Information

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IPC IPC(8): C07D241/44
CPCC07D241/44
Inventor 孙彬金灿颜志阳
Owner ZHEJIANG UNIV OF TECH
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