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Method for regioselectively synthesizing 7-arylseleno quinoxalinone derivative

A technology of quinoxalinone and synthetic method, which is applied in the field of synthesis of 7-arylselenoquinoxalinone derivatives, can solve the problems of narrow application range of substrates, etc., achieve easy preparation of raw materials, reduce waste of resources, reduce Effects of Environmental Pollution

Pending Publication Date: 2020-09-22
HENAN UNIVERSITY OF TECHNOLOGY
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0012] In 2018, Yang Daoshan et al. (Yang DS, Li GQ, Xing, CY, et al. Org. Chem. Front., 2018, 5, 2974-2979.) reported that 3-arylamino aromatic Soybein derivatives and diaryl diselenides in the oxidizing agent (NH 4 ) 2 S 2 o 8 Under the action of 3-aryl selenyl-4-arylamino coumarin derivatives, the shortcoming of this reaction is that the 4-position of coumarin needs to be pre-functionalized, and the scope of application of the substrate is narrow. The reaction formula is as follows:
At present, the functionalization of quinoxalinone mainly includes alkylation, arylation, benzylation, phosphorylation, acylation, alkoxylation, fluoroalkylation, alkylthio Etherification, etc. There are few reports on the research methods of introducing aryl selenyl functional groups on the quinoxalinone skeleton, especially the synthetic method of introducing aryl selenyl functional groups at the 7-position of quinoxalinone with high selectivity has not been reported so far, and still exists. The necessity of continuing research and exploration is also the basis and motivation for the present invention to be accomplished

Method used

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  • Method for regioselectively synthesizing 7-arylseleno quinoxalinone derivative
  • Method for regioselectively synthesizing 7-arylseleno quinoxalinone derivative
  • Method for regioselectively synthesizing 7-arylseleno quinoxalinone derivative

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0033] Example 1.R 1 =-Me, R 2 When =-Ph, the preparation of 1-methyl-7-phenylselenoquinoxalin-2 (1H)-one derivatives

[0034] Add 1-methylquinoxalin-2(1H)-one (0.2mmol, 32.0mg) and diphenyldiselenide (0.2mmol, 62.8mg) in a 25mL round bottom flask, then add 70% peroxygen An aqueous solution of tert-butanol (0.5mmol, 65.0mg), and finally 2mL of 1,2-dichloroethane was added as a solvent. React at 80°C for 5 hours; after the reaction, remove the solvent under reduced pressure, add 10 mL of ethyl acetate to the residue, wash twice with 20 mL of saturated brine; wash the organic layer with anhydrous Na 2 SO 4 After drying and concentration under reduced pressure, it was separated and purified by column chromatography (eluent: ethyl acetate / petroleum ether=1 / 5) to obtain 0.054 g of a colorless solid with a yield of 85.0%.

[0035]

[0036]1 H NMR (400MHz, CDCl 3 )δ:8.26(s,1H),7.95(d,J H-H =1.9Hz,1H),7.65(dd,J H-H =8.6Hz,J H-H =1.9Hz,1H),7.50-7.48(m,2H),7.30-7.27(m,3H),7.2...

Embodiment 2

[0037] Example 2.R 1 =-CH 2 CH 2 CH 3 , R 2 =-Ph, the preparation of 1-n-propyl-7-phenylselenoquinoxalin-2 (1H)-one derivatives

[0038] Add 1-propylquinoxaline-2(1H)-one (0.2mmol, 37.6mg) and diphenyldiselenide (0.2mmol, 62.8mg) into a 25mL round bottom flask, then add di-tert-butoxy Base peroxide (0.5mmol, 73.0mg), and finally add 2mL DMF as solvent. React at 90°C for 6 hours; after the reaction, remove the solvent under reduced pressure, add 10 mL of ethyl acetate to the residue, wash twice with 20 mL of saturated brine; wash the organic layer with anhydrous Na 2 SO 4 After drying and concentration under reduced pressure, it was separated and purified by column chromatography (eluent: ethyl acetate / petroleum ether=1 / 6) to obtain 0.060 g of a colorless solid with a yield of 87.0%.

[0039]

[0040] 1 H NMR (400MHz, CDCl 3 )δ:8.23(s,1H),7.94(d,J H-H =1.9Hz,1H),7.61(dd,J H-H =8.7Hz,J H-H =1.9Hz,1H),7.49-7.46(m,2H),7.26-7.24(m,3H),7.21(d,J H-H =8.7Hz, 1H), 4.13(...

Embodiment 3

[0041] Example 3.R 1 =-CH 2 COOC 2 h 5 , R 2 When =-Ph, the preparation of 1-ethoxyethyl-7-phenylselenoquinoxalin-2 (1H)-one derivatives

[0042] In a 25mL round bottom flask, add 1-ethoxyethylquinoxalin-2(1H)-one (0.2mmol, 46.4 mg) and diphenyl diselenide (0.2mmol, 62.8mg), then add Selectfluor Fluorine reagent (0.5mmol, 177.0mg), finally add 1mL MeCN and 1mL H 2 O is a mixed solvent. React at 80°C for 2 h; after the reaction, remove the solvent under reduced pressure, add 10 mL of ethyl acetate to the residue, wash twice with 20 mL of saturated brine; wash the organic layer with anhydrous Na 2 SO 4 After drying and concentration under reduced pressure, it was separated and purified by column chromatography (eluent: ethyl acetate / petroleum ether=1 / 3) to obtain 0.070 g of a colorless solid with a yield of 90.0%.

[0043]

[0044] 1 H NMR (400MHz, CDCl 3 )δ:8.31(s,1H),7.97(d,J H-H =1.9Hz,1H),7.61(dd,J H-H =8.6Hz,J H-H =1.9Hz,1H),7.52-7.50(m,2H),7.31-7.29(m,3H),6...

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Abstract

The invention discloses a preparation method of a 7-arylseleno quinoxalinone derivative (I), and belongs to the technical field of organic synthetic chemistry. The 7-arylseleno quinoxalinone derivative is synthesized by taking a substituted quinoxaline-2 (1H)-ketone derivative and diaryl diselenide as raw materials and a Selectfluor fluorine reagent and the like as an oxidizing agent without metalcatalysis. Compared with an existing synthesis method, the synthesis method has the following advantages that (1) the 7-arylseleno quinoxalinone derivative is synthesized in one step, raw materials and reagents are cheap and easy to obtain, the cost is low, and the application prospect is good; (2) only quinoxalinone 7-carbon with low electron cloud density is subjected to arylselenylation, and high regioselectivity is achieved; (3) the reaction conditions are mild, the reaction is carried out under the air condition, the yield is high, the operation is convenient, and the industrial production is facilitated. The derivative has potential application in the fields of medicine, chemical engineering, materials and the like, and a new way is provided for synthesis of the 7-arylseleno quinoxalinone derivative.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis, and in particular relates to a synthesis method of 7-aryl selenylquinoxalinone derivatives. Background technique [0002] Selenium has anti-cancer, anti-oxidation, enhances human immunity, antagonizes harmful heavy metals, regulates vitamin absorption, regulates protein synthesis in the human body, and enhances reproductive function. It is also an important component of peroxidase in muscles and has been widely used Synthesis of medicines, polymer materials, and pesticides, for example, Ebselen (Ebselen) is a new type of anti-inflammatory drug molecule containing a selenide structure developed by Japan's Daiichi Pharmaceutical and Germany's Nattermann. Organoselenium compounds widely exist in natural products and biologically active organic molecules, and have anti-senile dementia, prevention of Parkinson's disease, thymus cancer, and anti-tumor effects. In addition, selenium is also t...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D241/44C07D409/12
CPCC07D241/44C07D409/12
Inventor 马梦瑶杨亮茹张洋杨腾宇袁金伟游利琴肖咏梅毛璞屈凌波
Owner HENAN UNIVERSITY OF TECHNOLOGY
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