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Synthesis method of 3-gamma-lactam/amide alkyl substituted quinoxalinone derivative

A quinoxalinone and amidoalkyl technology, which is applied in the field of synthesis of 3-γ-lactam/amidoalkyl substituted quinoxalinone derivatives, can solve the problem of increasing post-processing difficulty, high reaction temperature, and substrates. Scope limitation and other issues, to achieve the effect of being suitable for popularization and application, simple reaction operation and mild reaction conditions

Active Publication Date: 2021-08-17
ZHEJIANG UNIV OF TECH
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] In 2016, it was reported in the literature (J.Org.Chem.2016,81,3017-3022) that persulfate catalyzed the carbon-carbon coupling of benzothiazole and N-alkylamide under thermal initiation conditions, although this method can efficiently Construct amidoalkyl substitution of benzothiazole, but require higher reaction temperature and equivalent potassium persulfate
This reaction requires a specific substrate, the substrate range is limited, and a metal catalyst is used, which increases the difficulty of post-treatment (J.Org.Chem.2020, 85, 4430-4440)

Method used

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  • Synthesis method of 3-gamma-lactam/amide alkyl substituted quinoxalinone derivative
  • Synthesis method of 3-gamma-lactam/amide alkyl substituted quinoxalinone derivative
  • Synthesis method of 3-gamma-lactam/amide alkyl substituted quinoxalinone derivative

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0021] Example 1 3-(1-methyl-5-oxopyrrolidin-2-yl)quinoxalin-2(1H)-one (IV-a)

[0022]

[0023] Add compound (I) quinoxalin-2-one (58.4mg, 0.4mmol), potassium persulfate (27mg, 0.1mmol), 1-methylpyrrolidone (396mg, 4mmol) in a three-necked flask equipped with magnetic stirring, Water (1.5 mL) was added to the mixture, the mixture was exposed to the air and irradiated under 3W blue light, stirred and reacted at 25°C for 19 hours, the reaction solution was washed with saturated brine, the mixture was extracted with ethyl acetate, and the combined organic Anhydrous Na 2 SO 4 Dry and concentrate under reduced pressure. The crude product was purified on a silica gel column using dichloromethane / methanol at a volume ratio of 50:1 to obtain the target product with a yield of 62% and an HPLC purity of 98.6%. 1 H NMR (400MHz, DMSO-d 6 )δ12.51(s,1H),7.74(dd,J=8.2,1.4Hz,1H),7.55–7.51(m,1H),7.33–7.28(m,2H),5.05(dd,J=9.0, 3.0Hz,1H),2.71(s,3H),2.46–2.34(m,1H),2.32–2.20(m,2H),1.99–1....

Embodiment 2

[0024] Example 2 6,7-Dimethyl-3-(1-methyl-5-oxopyrrolidin-2-yl)quinoxalin-2(1H)-one (IV-b)

[0025]

[0026] Add compound (I) 6,7-dimethylquinoxalin-2-one (69.6mg, 0.4mmol), potassium persulfate (54mg, 0.2mmol), 1-methyl Pyrrolidone (198mg, 2mmol), acetonitrile (1.5mL) was added to the mixture, the mixture was exposed to air and irradiated under 3W white light, stirred and reacted at 25°C for 18 hours, the reaction solution was washed with saturated brine, and the mixture was washed with acetic acid Ethyl ether extraction, combined organic layer with anhydrous Na 2 SO 4 Dry and concentrate under reduced pressure. The crude product was purified on a silica gel column using dichloromethane / methanol at a volume ratio of 60:1 to obtain the target product with a yield of 55% and an HPLC purity of 98.8%.

[0027] 1 H NMR (400MHz, DMSO-d 6 )δ12.38(s,1H),7.52(s,1H),7.07(s,1H),5.02(dd,J=8.8,3.2Hz,1H),2.69(s,3H),2.46–2.34(m ,1H),2.30(s,3H),2.27(s,3H),2.24–2.17(m,2H),1.93–1.86(m...

Embodiment 3

[0028] Example 3 1-methyl-3-(1-methyl-5-oxopyrrolidin-2-yl)quinoxalin-2(1H)-one (IV-c) (a:b=100:3, Crude product was detected by NMR)

[0029]

[0030]Add compound (I) 1-methylquinoxalin-2-one (64mg, 0.4mmol), ammonium persulfate (22.8mg, 0.1mmol), 1-methylpyrrolidone (99mg , 1mmol), dichloromethane (1.5mL) was added to the mixture, the mixture was exposed to the air and irradiated under 3W green light, stirred and reacted at 25°C for 20 hours, the reaction solution was washed with saturated brine, and the mixture was washed with acetic acid Ethyl ether extraction, combined organic layer with anhydrous Na 2 SO 4 Dry and concentrate under reduced pressure. The crude product was purified on a silica gel column using n-hexane / ethyl acetate at a volume ratio of 1:1 to obtain the target product with a yield of 79.5% and an HPLC purity of 97.8%. 1 H NMR (400MHz, CDCl 3 )δ7.84(d,J=8.0Hz,1H),7.57(t,J=7.8Hz,1H),7.37–7.32(m,2H),5.16(dd,J=8.6,2.6Hz,1H), 3.70(s,3H),2.84(s,3H),2.5...

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Abstract

The invention discloses a synthesis method of a 3-gamma-lactam / amide alkyl substituted quinoxalinone derivative, which comprises the following steps: adding a quinoxaline-2-ketone compound, an amide compound and a catalyst into a solvent according to a certain proportion, exposing in air, stirring and reacting at 25-70 DEG C under the illumination of a light source, and after the reaction is finished, carrying out post-treatment on the reaction liquid to obtain the target compound 3-position amide alkyl substituted quinoxalinone derivative. According to the green synthesis method, the 3-gamma-lactam / amide alkyl substituted quinoxalinone derivative is synthesized from a quinoxaline-2-ketone compound through a C-C coupling method by taking oxygen in air as an oxidizing agent under the catalysis of visible light / persulfate. The method has the advantages of cheap and easily available raw materials, simple process, mild reaction conditions, environmental friendliness, high product purity and yield and the like.

Description

technical field [0001] The present invention relates to a kind of synthetic method of 3-γ-lactam / amide alkyl substituted quinoxalinone derivatives, specifically a kind of in the presence of visible light / persulfate catalyst, using oxygen in the air as oxidant to produce quinoxalinone A green synthesis method for synthesizing 3-γ-lactam / amidoalkyl substituted quinoxalinone derivatives from oxalin-2-ones via C-C coupling. Background technique [0002] Quinoxaline derivatives have important application value, and the C-3 functionalization reaction of quinoxalinone is a research hotspot. [0003] Amide and lactam structures are ubiquitous in natural products and medicines, and the change of substituent structure on the γ-lactam ring makes 2-pyrrolidone derivatives exhibit different biological activities, such as anti-inflammatory, anti-tumor, anti-HIV , Anti-senile dementia, etc. The structure modification of this kind of compound has good research prospect. [0004] In 2016,...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D403/04C07D413/04C07D241/44C07D403/06
CPCC07D403/04C07D413/04C07D241/44C07D403/06Y02B20/00
Inventor 周嘉第李坚军任全磊周鹏
Owner ZHEJIANG UNIV OF TECH
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