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Synthetic method for 1H-pyrrole-2,5-dione derivative

A technology of derivatives and diketones, applied in the field of preparing 1H-pyrrole-2, can solve the problems of unfriendly environment, low yield of suzuki reaction and the like

Active Publication Date: 2018-05-01
CHONGQING UNIV OF ARTS & SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0009] Generally, the suzuki reaction has a low reaction yield and is not environmentally friendly due to the use of metal catalysts

Method used

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  • Synthetic method for 1H-pyrrole-2,5-dione derivative
  • Synthetic method for 1H-pyrrole-2,5-dione derivative
  • Synthetic method for 1H-pyrrole-2,5-dione derivative

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Experimental program
Comparison scheme
Effect test

Embodiment 1-10

[0078] According to the above-mentioned general preparation method, the following compounds 1-10 were prepared using corresponding starting materials.

[0079] Compound 1 (yield: 75% purity: greater than 95%)

[0080]

[0081] 1 H NMR (400MHz, CDCl 3 )δ7.47-7.38(m, 2H), 7.36-7.27(m, 3H), 7.16(d, J=8.8Hz, 2H), 7.12(s, 1H), 7.06-6.94(m, 2H), 6.77 -6.65(m, 2H), 6.49(d, J=8.8Hz, 2H), 4.76(s, 2H), 3.77(s, 3H).

[0082] 13 C NMR (100MHz, CDCl 3 )δ 171.81, 168.35, 159.27, 136.52, 135.64, 134.34, 131.34, 131.13, 128.70, 128.64, 127.84, 122.51, 121.50, 117.01, 113.10, 113.10, 104.22, 55.88

[0083] Compound 2 (yield: 73% purity: greater than 95%)

[0084]

[0085] 1 H NMR (400MHz, CDCl 3 )δ7.45(d, J=7.0Hz, 2H), 7.38-7.27(m, 3H), 7.15-7.06(m, 3H), 7.05-6.95(m, 5H), 6.62(d, J=7.6Hz , 2H), 4.78(s, 2H).

[0086] 13 C NMR (100MHz, CDCl 3 )δ 171.81, 168.25, 136.59, 136.28, 136.13, 129.74, 129.32, 128.69, 128.67, 128.31, 127.81, 127.34, 127.27, 124.55, 121.55, 102.79, 77.34,...

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Abstract

The invention provides a method for synthesizing a 1H-pyrrole-2,5-dione derivative through a one-pot multi-component reaction. The method is simple in operation steps and can prepare the 1H-pyrrole-2,5-dione derivative with high yield and high purity.

Description

technical field [0001] The present application relates to a process for the preparation of 1H-pyrrole-2,5-dione derivatives. Background technique [0002] 1H-pyrrole-2,5-dione derivatives have good antibacterial activity and antiviral activity, and can be used as angiogenesis inhibitors and kinase inhibitors, among which there is a relatively strong effect on glycogen synthase-3 (GSK-3) The strong inhibitory effect can be used as an important lead compound for treating tumors. In addition, 1H-pyrrole-2,5-dione derivatives can also inhibit homologous recombination (HR, Homologous Recombination) in cells, thereby killing cells. [0003] Currently, the synthesis of 1H-pyrrole-2,5-dione derivatives requires at least three steps. For example, Hiroaki Imoto, Kensuke Naka et al. described in Chem.Eur.J.2015, 21, 12105-12111 that 2,3-dichloromaleic anhydride was used as a raw material, followed by a 2-step reaction with an amino compound and then a suzuki reaction Similar compoun...

Claims

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Application Information

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IPC IPC(8): C07D207/456C07D405/04
CPCC07D207/456C07D405/04
Inventor 陈中祝徐志刚唐典勇孟江平
Owner CHONGQING UNIV OF ARTS & SCI