Method for preparing 3-acyl quinoxaline ketone derivative

A technology for acylquinoxalinone and derivatives, which is applied in the field of synthesis of 3-acylquinoxalinone derivatives, which can solve the problems that do not conform to the development of green chemistry, require transition metal catalysis, and difficult to obtain raw materials, etc., so as to avoid purification The effect of mild treatment and reaction conditions and a wide range of applications

Active Publication Date: 2018-05-15
HENAN UNIVERSITY OF TECHNOLOGY
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Although these documents report methods for the synthesis of 3-acylquinoxalinone derivatives, these methods often have disadvantages such as difficult access to raw materials, many reaction steps, poor atom economy, or the need for transition metal catalysis, and do not conform to the development of green chemistry. requirements, so that their application in actual production is greatly restricted

Method used

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  • Method for preparing 3-acyl quinoxaline ketone derivative
  • Method for preparing 3-acyl quinoxaline ketone derivative
  • Method for preparing 3-acyl quinoxaline ketone derivative

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0019] Example 1.R 1 =-R 2 =-H, R 3 When =-Ph, the preparation of 3-(benzoyl)quinoxalin-2-one derivatives

[0020] Add quinoxalin-2-one (0.2mmol, 29.2mg) and benzaldehyde (0.4mmol, 42.4mg) in 25mL round-bottomed flask, then add mass percentage content 70% peroxy tert-butanol aqueous solution (0.8mmol, 104mg), and finally add 2mL of 1,2-dichloroethane as solvent. React at 70°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 concentrating under reduced pressure, it was separated and purified by column chromatography (eluent: ethyl acetate / petroleum ether=1 / 2) to obtain 0.043 g of a colorless solid with a yield of 85.0%.

[0021]

[0022] Colorless solid, melting point mp 251-252°C. 1 H NMR(400MHz,DMSO)δ:12.88(s,1H), 7.98(d,J H-H =7.0Hz,2H),7.83(dd,J H-H =8.1Hz,J H-H =1.1Hz,1H),7.74(t,J H-H =...

Embodiment 2

[0023] Example 2.R 1 =-PhCH 2 , R 2 =-H,R 3 Preparation of 1-benzyl-3-(benzoyl)quinoxalin-2-one derivatives when =-Ph

[0024]Add 1-benzylquinoxalin-2-one (0.2mmol, 47.2mg) and benzaldehyde (0.4mmol, 42.4mg) in a 25mL round-bottomed flask, and then add 70% mass percent peroxy tert-butanol aqueous solution (0.8mmol, 104 mg), and finally 2mL of 1,2-dichloroethane was added as a solvent. React at 65°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 concentrating under reduced pressure, it was separated and purified by column chromatography (eluent: ethyl acetate / petroleum ether=1 / 6) to obtain 0.054 g of a colorless solid with a yield of 80.0%.

[0025]

[0026] Yellow solid, melting point 128-129°C. 1 H NMR (400MHz, CDCl 3 )δ:8.01(dd,J H-H =8.0Hz,J H-H =1.4Hz,2H),7.92(dd,J H-H =8.4Hz,J H-H ...

Embodiment 3

[0027] Example 3.R 1 =-C 6 h 13 , R 2 =-H,R 3 When =-Ph, the preparation of 1-n-hexyl-3-(benzoyl)quinoxalin-2-one derivatives

[0028] Add 1-n-hexylquinoxalin-2-one (0.2mmol, 46.0mg) and benzaldehyde (0.4mmol, 42.4mg) in a 25mL round bottom flask, then add di-tert-butoxy peroxide (0.6mmol, 87.6 mg), and finally add 2 mL of acetone as a solvent. React at 60°C for 8 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 / 8) to obtain 0.055 g of a colorless solid with a yield of 83.0%.

[0029]

[0030] viscous liquid. 1 H NMR (400MHz, CDCl 3 )δ:7.98-7.96(m,2H),7.93(dd,J H-H =7.8 Hz,J H-H =1.3Hz,1H),7.68-7.59(m,2H),7.47(t,J H-H =7.8Hz,2H),7.41-7.37(m,2H), 4.27(t,J H-H =7....

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Abstract

The invention discloses a method for preparing a 3-acyl quinoxaline ketone derivative (I) and belongs to the field of organic chemistry The method comprises the following steps: by taking a substituted quinoxaline-2-ketone derivative and aldehyde or benzyl alcohol as raw materials, and a 70% tert-butyl hydroperoxide (TBHP) solution as an oxidant, performing a heating reaction in a solvent withoutmetal catalysis, thereby synthesizing the 3-acyl quinoxaline ketone derivative. Compared with a conventional synthesis method, the method has the advantages that firstly, the raw materials are cheap and easy to obtain, the 3-acyl quinoxaline ketone derivative is synthesized at one step, the cost is low, and good application prospects can be achieved; secondly, the method is gentle in reaction condition, high in yield, convenient to operate, beneficial to industrial production and the like, and the reactions are carried out under an air condition. The derivative has potential application in fields such as medicines, chemical engineering and materials, and the invention provides a novel way for synthesis of 3-acyl quinoxaline ketone derivatives. (Refer to Specification).

Description

technical field [0001] The invention belongs to the technical field of organic synthesis, and in particular relates to a synthesis method of 3-acylquinoxalinone derivatives. Background technique [0002] Quinoxalinone is a common pharmacophore in the field of drug design. Derivatives containing the core of this structure have a variety of pharmacological activities and are widely used as antitumor agents, antibacterial agents, HIV-I reverse transcriptase inhibitors, anticoagulant Blood agents, hypoglycemic agents, etc., are the structural skeleton of many natural products, and they are playing an increasingly important role in the field of chemistry. Among the numerous quinoxalinone derivatives, 3-acylquinoxalinone derivatives, as important structural units, also have important biological activities, such as tumor cell proliferation inhibitors, dishidine reductase inhibitors, antibacterial and antibacterial Tumor function, and often used in the synthesis of drugs, natural p...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D241/44C07D409/06
CPCC07D241/44C07D409/06
Inventor 袁金伟游利琴傅俊豪肖咏梅毛璞杨亮茹屈凌波
Owner HENAN UNIVERSITY OF TECHNOLOGY
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