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3-acyl pyridine compound synthetic method

A synthesis method and technology of acylpyridine, which is applied in the field of synthesis of 3-acylpyridine compounds, can solve problems such as difficult availability of raw materials, poor atom economy, and many reaction steps, and achieve a wide application range, simple operation, and high synthesis efficiency. Effect

Active Publication Date: 2018-01-19
HENAN NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Although there are some synthetic methods of 3-acylpyridine compounds, these methods generally have disadvantages such as difficult access to raw materials, many reaction steps, poor atom economy, and high environmental factors. These shortcomings make their application in actual production very difficult. big limit

Method used

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Experimental program
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Embodiment 1

[0020]

[0021] Add 3-amino-1-phenyl-2-buten-1-one (2a, 0.5mmol, 80.6mg) into a 15mL reaction tube filled with N,N-dimethylformamide (2mL) and stir After dissolving, add propiophenone (1a, 0.6mmol, 80μL), Cu(OAc) 2 (0.05mmol, 9.1mg), 2,2'-bipyridine (bpy, 0.1mmol, 15.6mg) and 2,2,6,6-tetramethylpiperidine nitrogen oxide (TEMPO, 0.5mmol, 78.1mg) , the reaction tube was sealed in the presence of air, and then placed in an oil bath at 120° C. and stirred for 20 h. After the reaction was completed, the reaction tube was cooled to room temperature, water was added to quench the reaction, extracted with ethyl acetate (8 mL×3), and the organic phase was washed with water and saturated brine in sequence, and dried over anhydrous sodium sulfate. It was filtered, spin-dried, and separated by silica gel column (petroleum ether / ethyl acetate=20 / 1) to obtain the product 3a (105 mg, 77%) as a white solid. The characterization data of this compound are as follows: 1 H NMR (400MHz, CDCl...

Embodiment 2

[0023] Add 2a (0.5mmol, 80.6mg) into a 15mL reaction tube filled with toluene (2mL), stir to dissolve, then add propiophenone (1a, 0.6mmol, 80μL), Cu(OAc) 2 (0.05mmol, 9.1mg), 2,2'-bipyridine (0.1mmol, 15.6mg) and TEMPO (0.5mmol, 78.1mg), in the presence of air, the reaction tube was sealed, then placed in a 120 ° C oil bath and stirred Reaction 20h. After the reaction was completed, the reaction tube was cooled to room temperature, water was added to quench the reaction, and extracted with ethyl acetate (8 mL×3), and then the organic phase was washed with water and saturated brine in sequence, and dried over anhydrous sodium sulfate. It was filtered, spin-dried, and separated by silica gel column (petroleum ether / ethyl acetate=20 / 1) to obtain the product 3a (93 mg, 68%) as a white solid.

Embodiment 3

[0025] Add 2a (0.5mmol, 80.6mg) into a 15mL reaction tube containing chlorobenzene (2mL), stir to dissolve, then add 1a (0.6mmol, 80μL), Cu(OAc) 2 (0.05mmol, 9.1mg), 2,2'-bipyridine (0.1mmol, 15.6mg) and 4-hydroxy-2,2,6,6-tetramethylpiperidine nitrogen oxide (4-HO-TEMPO, 0.5mmol, 86.1mg), the reaction tube was sealed in the presence of air, and then placed in an oil bath at 120°C and stirred for 20h. After the reaction was completed, the reaction tube was cooled to room temperature, water was added to quench the reaction, and extracted with ethyl acetate (8 mL×3), and then the organic phase was washed with water and saturated brine in sequence, and dried over anhydrous sodium sulfate. It was filtered, spin-dried, and separated by silica gel column (petroleum ether / ethyl acetate=20 / 1) to obtain the product 3a (91 mg, 67%) as a white solid.

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Abstract

The invention discloses a 3-acyl pyridine compound synthetic method, which belongs to the technical field of organic synthesis. The synthetic method takes an enaminone compound and an alpha, beta-saturated ketone compound or an alpha, beta-saturated aldehyde compound as raw materials, and a 3-acyl pyridine compound is prepared under effect of a catalyst, a ligand and an oxidizing agent through a one-pot multi-step series reaction. The method has the advantages of simple operation, mild condition, and wide substrate application scope, and is suitable for industrial production.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis, and in particular relates to a synthesis method of 3-acylpyridine compounds. Background technique [0002] 3-Acylpyridine compounds are important nitrogen-containing heterocyclic compounds, and their structural skeletons are widely found in natural products. In addition, 3-acylpyridine compounds are also key intermediates for the preparation of various fine chemicals, and have a wide range of applications in the fields of materials and pharmaceuticals. Although there are some synthetic methods of 3-acylpyridine compounds, these methods generally have disadvantages such as difficult access to raw materials, many reaction steps, poor atom economy, and high environmental factors. These shortcomings make their application in actual production very difficult. Big restrictions. Therefore, researching and developing new methods for synthesizing 3-acylpyridine compounds from cheap and easy-to...

Claims

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Application Information

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IPC IPC(8): C07D213/50C07D405/04C07D409/04C07D215/20
Inventor 范学森陈光王泽张新迎
Owner HENAN NORMAL UNIV
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