Method for synthesizing 3-acyl hydrogenated azepine compounds

A technology of acyl hydrogenation azepine and synthesis method, which is applied in the direction of organic chemistry, etc., can solve the problems of limited synthesis method, low regioselectivity, and difficult synthesis of reaction substrate, so as to avoid the separation and purification process of intermediates and achieve high atom economy , The effect of copper salt economy

Active Publication Date: 2018-09-28
HENAN NORMAL UNIV
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Problems solved by technology

[0003] It should be pointed out that although 3-acylazepine compounds have high research value, their effective synthesis methods are still very limited, and these meth

Method used

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  • Method for synthesizing 3-acyl hydrogenated azepine compounds
  • Method for synthesizing 3-acyl hydrogenated azepine compounds
  • Method for synthesizing 3-acyl hydrogenated azepine compounds

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Embodiment 1

[0017]

[0018] 1a (0.5mmol, 88mg), 2a (0.6mmol, 90mg), acetonitrile (3mL), copper bromide (0.05mmol, 11mg) and di-tert-butyl peroxide (1mmol, 183μL) were sequentially added into the reaction tube, The reaction was stirred at 60° C. for 24 h under an atmosphere of air (1 atm). Then 10 mL of saturated brine was added to quench the reaction, extracted with ethyl acetate (10 mL×3), and the organic phases were combined and dried over anhydrous sodium sulfate. It was filtered, spin-dried, and separated on a silica gel column (petroleum ether / ethyl acetate=5 / 1) to obtain the syrupy product 3a (91 mg, 66%). The characterization data of this compound are as follows: 1 H NMR (400MHz, CDCl 3 )δ: 1.93-2.00(m, 4H), 2.84(t, J=6.4Hz, 2H), 4.03(t, J=6.0Hz, 2H), 6.96(d, J=8.0Hz, 2H), 7.04( t,J=7.2Hz,1H),7.25-7.29(m,3H),7.33-7.39(m,3H),7.52(dd,J 1 =7.6Hz,J 2 =1.6Hz,2H). 13 C NMR (100Hz, CDCl 3 )δ: 23.5, 25.3, 27.5, 50.6, 119.1, 119.4, 123.7, 128.0, 128.5, 129.5, 129.8, 141.2, 146.5, ...

Embodiment 2

[0020] 1a (0.5mmol, 88mg), 2a (0.6mmol, 90mg), acetonitrile (3mL), copper acetate (0.05mmol, 9mg) and di-tert-butyl peroxide (1mmol, 183μL) were sequentially added to the reaction tube. The reaction was stirred at 60° C. for 24 h under air (1 atm) atmosphere. Then 10 mL of saturated brine was added to quench the reaction, extracted with ethyl acetate (10 mL×3), and the organic phases were combined and dried over anhydrous sodium sulfate. It was filtered, spin-dried, and separated on a silica gel column (petroleum ether / ethyl acetate=5 / 1) to obtain the syrupy product 3a (58 mg, 42%).

Embodiment 3

[0022] 1a (0.5mmol, 88mg), 2a (0.6mmol, 90mg), acetonitrile (3mL), copper sulfate pentahydrate (0.05mmol, 12mg) and di-tert-butyl peroxide (1mmol, 183μL) were sequentially added into the reaction tube, The reaction was stirred at 60° C. for 24 h under an atmosphere of air (1 atm). Then 10 mL of saturated brine was added to quench the reaction, extracted with ethyl acetate (10 mL×3), and the organic phases were combined and dried over anhydrous sodium sulfate. It was filtered, spin-dried, and separated on a silica gel column (petroleum ether / ethyl acetate=5 / 1) to obtain the syrupy product 3a (44 mg, 32%).

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Abstract

The invention discloses a method for synthesizing 3-acyl hydrogenated azepine compounds, and belongs to the technical field of organic synthesis. The method comprises the steps of: adopting a seven-membered cyclic amine compound and 2-oxo-2-aryl acetic acid as raw materials, and performing a one-pot serial reaction to obtain the 3-acyl hydrogenated azepine compound directly, and the method comprises the specific operation steps of: dissolving the seven-membered cyclic amine compound 1 and 2-oxo-2-aryl acetic acid 2 in an organic solvent, then adding a copper salt catalyst and an oxidizing agent, and performing heating to raise the temperature for a reaction to obtain the 3-acyl hydrogenated azepine compound 3. The method has the advantages of a convenient operation process, mild conditions, a wide application range of the substrates and a potential prospect suitable for industrial amplification.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis, and in particular relates to a synthesis method of 3-acyl hydrogenated azepine compounds. Background technique [0002] 3-Acylazepines are an important class of seven-membered nitrogen-containing heterocycles. Compared with five-membered and six-membered nitrogen-containing heterocycles, although the distribution of seven-membered nitrogen-containing heterocycles in nature is relatively small, its remarkable pharmaceutical activity and unique reactivity make it an attractive choice for organic synthesis and drug development. The relevant research results also have important theoretical significance and application value. [0003] It should be pointed out that although 3-acylazepine compounds have high research value, their effective synthesis methods are still very limited, and these methods still have the disadvantages of difficult synthesis of reaction substrates, the need to use nob...

Claims

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Application Information

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IPC IPC(8): C07D223/04
CPCC07D223/04
Inventor 张新迎师晓楠范学森陈茜
Owner HENAN NORMAL UNIV
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