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Method for synthesizing polysubstituted pyridin-2(1H)-one

A technology of ketone compounds and synthetic methods, applied in the field of organic synthesis, can solve the problems of complex steps, low yield, harsh reaction conditions and the like

Inactive Publication Date: 2008-02-13
NORTHEAST NORMAL UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] The object of the present invention is to provide a multi-substituted pyridine-2(1H)- A Novel Synthetic Method of Ketone Compounds

Method used

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  • Method for synthesizing polysubstituted pyridin-2(1H)-one
  • Method for synthesizing polysubstituted pyridin-2(1H)-one
  • Method for synthesizing polysubstituted pyridin-2(1H)-one

Examples

Experimental program
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Effect test

Embodiment 1

[0015] In a 50 ml round-bottom flask, add dry N,N-dimethylformamide (5 ml), cool to 0°C, add phosphorus oxychloride (4.0 mmol) dropwise within 30 minutes, and stir at 0°C In 20 minutes, add α-acetyl α-methylacetanilide (2 mmol) in N,N-dimethylformamide (20 mL) solution dropwise to the system within 30 minutes, then increase the temperature to 80°C and continue After stirring for 2 hours, the reaction was stopped. The reaction solution was poured into 100 ml of saturated brine, extracted twice with 50 ml of dichloromethane, and the organic phases were combined, washed twice with 50 ml of water, dried with 10 g of anhydrous sodium sulfate, and filtered. The organic solvent was evaporated, and a white product was obtained through silica gel column chromatography with a yield of 91%.

[0016]

Embodiment 2

[0018] In a 50 ml round bottom flask, add dry N,N-dimethylformamide (5 ml), cool to 0°C, add phosphorus oxychloride (5.0 mmol) dropwise within 30 minutes, and stir at 0°C In 20 minutes, N-(4-methylphenyl)-α-acetyl-α-methylacetamide (2 mmol) of N,N-dimethylformamide ( 20ml) solution, and then heated to 80℃, continue to stir for 2 hours, stop the reaction, the reaction solution was poured into 100ml of saturated brine, were extracted twice with 50ml of dichloromethane, and the organic phases were combined and washed with 50ml of water. Then, 10 grams of anhydrous sodium sulfate were dried, filtered, and the organic solvent was evaporated. The white product was separated by silica gel column chromatography with a yield of 86%.

[0019]

Embodiment 3

[0021] In a 50 ml round bottom flask, add dry N,N-dimethylformamide (5 ml), cool to 0°C, add phosphorus oxychloride (6.0 mmol) dropwise within 30 minutes, and stir at 5°C 15 minutes, N-(4-chlorophenyl)-α-acetyl-α-methylacetamide (2 mmol) of N,N-dimethylformamide (20 Ml) solution, and then heated to 80°C, continue to stir for 2 hours to stop the reaction, the reaction solution was poured into 100 ml of saturated brine, extracted twice with 50 ml of dichloromethane, and the organic phases were combined and washed twice with 50 ml of water. , 10 grams of anhydrous sodium sulfate, dried, filtered, evaporated to remove the organic solvent, and separated by silica gel column chromatography to obtain a white product with a yield of 87%.

[0022]

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Abstract

The invention belongs to an organic synthesis method, in particular relating to a synthesis method for the tic substitute pyridine-2 (1 H)-ketone compounds with the acetyl-acetylamine compounds under the reaction conditions of the Vilsmeier. The phosphorus oxychloride or phosphorus tribromide N, N-dimethylformamide mix and react to form the Vilsmeier reagent used in the reaction. The newly prepared Vilsmeier reagent is added into the reaction bottle provided with the return condenser and the blender; a reaction raw material (I) N, N-dimethylformamide solution expressed in the reaction formula is added into the system; the temperature is risen; the corresponding multi substituting pyridine-2 (1 H)-ketone compound (II) can be made after the column chromatography of the silica gel; the production rate is between 60 and 95 percent according to different reactions. The synthetic steps of the invention are fewer; the application scope is wide; the raw material is easy to get; the price is low; the functional group of the products is rich; the reaction conditions are mild; the production rate is high; the operation is easy; the invention is easy for the process of industrialization.

Description

Technical field: [0001] The invention belongs to an organic synthesis method, and particularly relates to a synthetic method for synthesizing polysubstituted pyridine-2(1H)-ketone compounds under Vilsmeier reaction conditions with acetylacetamide compounds. Background technique: [0002] Pyridine-2(1H)-ketone compounds are an important class of six-membered nitrogen-containing heterocyclic compounds, which are widely found in natural products and have important biological and pharmaceutical activities. At the same time, they are a kind of multifunctional organic synthesis intermediates, pyridine -2(1H)-ketone compounds have been widely used in organic synthesis, especially the synthesis of heterocyclic compounds. Judging from the current literature, there are two main types of existing synthetic methods for this type of compound: one type is synthesized from pyridine compounds using pyridine salt chemistry or pyridine N-alkylation reaction; the other type is synthesized by chain-...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D213/64
Inventor 董德文向德轩梁永久潘伟王科伟黄杰
Owner NORTHEAST NORMAL UNIVERSITY
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