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Synthesis of 2-phenylimidazo[1,2-a]pyridoquinoxaline-2(1H)-one derivative

A technology of phenylimidazole and 2-a, which is applied in the field of compound preparation, can solve the problems of large amount of metal and the influence of drug activity detection, etc., and achieve the effect of low cost, few steps and short synthesis steps

Inactive Publication Date: 2018-06-19
CHONGQING UNIV OF ARTS & SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

There are also many metals that catalyze the reaction. Palladium, rhodium, rubidium, nickel, etc. can catalyze similar reactions, but compared with multi-component reactions, metal catalysts often contain less metal in the separation of the final product. Large, the activity detection of drugs is affected to a certain extent

Method used

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  • Synthesis of 2-phenylimidazo[1,2-a]pyridoquinoxaline-2(1H)-one derivative
  • Synthesis of 2-phenylimidazo[1,2-a]pyridoquinoxaline-2(1H)-one derivative
  • Synthesis of 2-phenylimidazo[1,2-a]pyridoquinoxaline-2(1H)-one derivative

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Embodiment 1

[0048] where R 1 is a hydrogen atom, R 2 is a hydrogen atom, R 3 For a hydrogen atom, that is, 3-(2-phenylimidazo[1,2- a ]pyridin-3-yl)quinoxaline-2(1 H )-ketone synthesis, the specific steps are as follows:

[0049] In a 20 ml microwave reaction tube, first dissolve Boc-protected aniline compound (1.0 mmol) and ethyl glyoxylate (1.0 mmol) in 10 ml of isopropanol, and react at 60°C for 30 minutes. Then 4-toluenesulfonyl chloride (0.2 mmol) and imidazo[1,2- a ] Pyridine compounds (1.0 mmol) were sequentially added to the solution, the reaction solution was stirred at 60°C for 5 hours, and then the reaction was detected by thin-layer chromatography. After the end of the reaction, the solution was blown dry with nitrogen. After dissolving in N,N-dimethylformamide (DMF, 10 ml), potassium carbonate (5 mmol) was added and reacted in a microwave oven at 160°C for 20 minutes. After the reaction tube was cooled to room temperature in a microwave oven, it was dissolved with ethyl ...

Embodiment 2

[0052] where R 1 is halogen, R 2 is a hydrogen atom, R 3 For a hydrogen atom, that is, 3-(8-bromo-2-phenylimidazo[1,2- a ]pyridin-3-yl)quinoxaline-2(1 H )-ketone synthesis, the specific steps are as follows:

[0053] In a 20 ml microwave reaction tube, first dissolve Boc-protected aniline compound (1.0 mmol) and ethyl glyoxylate (1.0 mmol) in 10 ml of isopropanol, and react at 60°C for 30 minutes. Then 4-toluenesulfonyl chloride (0.2 mmol) and bromoimidazo[1,2- a ] Pyridine compounds (1.0 mmol) were sequentially added to the solution, the reaction solution was stirred at 60°C for 5 hours, and then the reaction was detected by thin-layer chromatography. After the end of the reaction, the solution was blown dry with nitrogen. After dissolving in N,N-dimethylformamide (DMF, 10 ml), potassium carbonate (5 mmol) was added and reacted in a microwave oven at 160°C for 20 minutes. After the reaction tube was cooled to room temperature in a microwave oven, it was dissolved with e...

Embodiment 3

[0056] where R 1 Disubstituted by methyl and halogen, R 2 is a hydrogen atom, R 3 For a hydrogen atom, that is, 3-(8-bromo-6-methyl-2-phenylimidazo[1,2- a ]pyridin-3-yl-1)quinoxaline-2(1 H )-ketone synthesis, the specific steps are as follows:

[0057] In a 20 ml microwave reaction tube, first dissolve Boc-protected aniline compound (1.0 mmol) and ethyl glyoxylate (1.0 mmol) in 10 ml of isopropanol, and react at 60°C for 30 minutes. Then 4-toluenesulfonyl chloride (0.2 mmol) and methylbromoimidazo[1,2- a ] Pyridine compounds (1.0 mmol) were sequentially added to the solution, the reaction solution was stirred at 60°C for 5 hours, and then the reaction was detected by thin-layer chromatography. After the end of the reaction, the solution was blown dry with nitrogen. After dissolving in N,N-dimethylformamide (DMF, 10 ml), potassium carbonate (5 mmol) was added and reacted in a microwave oven at 160°C for 20 minutes. After the reaction tube was cooled to room temperature in...

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Abstract

The invention relates to a preparation method of a 2-phenyl-imidazo[1,2-a]pyridoquinoxaline-2(1H)-one ketone derivative. The method comprises the following steps: performing a multi-component reactionused as a basis to obtain a condensation product, performing simple post-treatment, deprotecting the post-treated condensation product under an alkaline condition, and performing microwave-assisted ring closure to obtain the 2-phenylimidazo[1,2-a]pyridoquinoxaline-2(1H)-one derivative with potential anticancer activity.

Description

technical field [0001] The invention belongs to the field of compound preparation methods, especially a 2-phenylimidazo[1,2- a ] Rapid preparation method and application of pyridoquinoxalin-2(1H)-one derivatives. Background technique [0002] Imidazopyridine derivatives generally have good biological activity, and have many applications in diabetes-related drugs, as well as anti-tumor and anti-bacterial. According to reports, this type of compound has many applications in the treatment of tumor-related cancer diseases, such as lung cancer, liver cancer, pancreatic cancer and blood-related cancers. In addition, quinoxaline derivatives are the pharmacophore of many biologically active compounds, and their derivatives have various pharmacological activities, and are widely used as antitumor agents, antibacterial agents, HIV-1 reverse transcriptase inhibitors, anticoagulants, Hypoglycemic agents, etc., also have broad development and application prospects. [0003] Such compo...

Claims

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Application Information

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IPC IPC(8): C07D471/04A61P35/00
CPCC07D471/04
Inventor 徐志刚陈中祝唐典勇孟江平
Owner CHONGQING UNIV OF ARTS & SCI
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