Method for preparing amide compound from 2-diazo-1, 3-dicarbonyl compound as acylating agent

A technology for dicarbonyl compounds and amide compounds, applied in the field of preparing amide compounds, can solve the problems of harsh reaction conditions, racemization of chiral compounds, influence and the like, and achieve the effects of mild reaction conditions, simple reaction operation and high reaction efficiency

Active Publication Date: 2017-04-05
山西师范大学
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Such as: acid chloride, acid anhydride, boron reagent, etc., which will produce a large number of by-products, which will bring inconvenience to separation and purification
In addition, due to the harsh reaction conditions, it will cause the racemization of chiral compounds
[0007] 2. Acid chloride, as the most commonly used acylating reagent, is often used in the preparation of amide compounds. The obvious disadvantages are: the reaction needs to add a base, and the chiral compound is prone to racemization; the reaction system will release HCl, and some are sensitive to acid The functional group (such as: Boc-) will be affected;
It has not been widely used due to harsh reaction conditions and other reasons.

Method used

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  • Method for preparing amide compound from 2-diazo-1, 3-dicarbonyl compound as acylating agent
  • Method for preparing amide compound from 2-diazo-1, 3-dicarbonyl compound as acylating agent
  • Method for preparing amide compound from 2-diazo-1, 3-dicarbonyl compound as acylating agent

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0055] The preparation method of N-butylbenzamide is as follows:

[0056] The structural formula is:

[0057]

[0058] Preparation process: Add 2-diazo-1,3-diphenylpropane-1,3-dione (375mg, 1.5mmol) and DMSO (1mL) sequentially into a reaction flask equipped with a stirring bar, and then add to the system Butylamine (1mmol) was added to the mixture, reacted at 20-50°C for 2.0 hours, the reaction was completed, water was added to the system to quench the reaction, and extracted three times with dichloromethane, the organic phases were combined, dried, the solvent was removed, and column chromatography was carried out. Separated to obtain N-butylbenzamide (90%, 160mg) with different substituents on the benzene ring with a purity of 99%

Embodiment 2

[0060] The preparation method of N-(cyclohexylmethyl) benzamide is as follows:

[0061] The structural formula is:

[0062]

[0063] Preparation process: Add 2-diazo-1,3-diphenylpropane-1,3-dione (375mg, 1.5mmol) and 1,4-dioxane ( 1mL), then add cyclohexylamine (1mmol, 113mg) to the system, and react at 20-50°C for 3.0 hours. After the reaction is completed, add water to the system to quench the reaction, and extract three times with dichloromethane, and combine the organic phases , dried, removed the solvent, and subjected to column chromatography to obtain N-(cyclohexylmethyl)benzamide (87%, 189 mg) with a purity of 99%.

Embodiment 3

[0065] The preparation method of N-benzylbenzamide is as follows:

[0066] The structural formula is:

[0067]

[0068] In the formula, R is H, OH, NH 2 , Cl

[0069] Preparation process: Add 2-diazo-1,3-diphenylpropane-1,3-dione (375mg, 1.5mmol)) and DMF (1mL) successively in a reaction flask equipped with a stirring bar, and then add Add substituted benzylamine (1mmol) to the system, and react at 20-50°C for 2.0 hours. After the reaction is completed, add water to the system to quench the reaction, and extract three times with dichloromethane, combine the organic phases, dry, remove the solvent, and Column chromatographic separation was carried out to obtain N-benzylbenzamide compounds with different substituents on the benzene ring with a purity of 99%.

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Abstract

The invention provides a method for preparing an amide compound from a 2-diazo-1, 3-dicarbonyl compound as an acylating agent under non-metallic catalysis and neutral conditions. The method uses 2-diazo-1, 3-dicarbonyl compound as a raw material and carries out different benzoyl protection on different amino compounds so that a series of amide compounds are prepared. The method is carried out under neutral conditions, prevents the limitation of reaction substrates under conventional alkaline conditions, and has mild reaction conditions, high reaction efficiency and a simple operation method. The method provides a new and convenient method for preparation of amide compounds and protection of amino groups and can be used in the fields of chemical medicine, biology and materials.

Description

technical field [0001] The invention belongs to the field of chemical industry, and specifically designs a method for preparing amide compounds by using 1,3-dicarbonyl compounds as acylation reagents under non-metallic neutral conditions. Background technique [0002] Amide bonds are ubiquitous in natural products and medicines, and amide compounds account for almost 25% of some important medicinal compounds and best-selling drugs. Because of the important role of amide compounds in organic chemistry, the simple and efficient preparation of amide compounds is also the goal that chemists have been pursuing. [0003] The synthesis methods of amide compounds reported in the existing literature can be roughly divided into three categories according to the difference of acylating reagents. [0004] 1. Amination reaction of carboxylic acid and its derivatives [0005] 1. Amination reaction of acid [0006] Due to the relatively low reactivity of carboxylic acids, the condensati...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C231/10C07C233/65C07C233/73C07C233/78C07C233/66C07C235/46C07D405/12C07D211/26C07B43/06
CPCC07B43/06C07C231/10C07D211/26C07D405/12C07C233/65C07C233/73C07C233/78C07C233/66C07C235/46
Inventor 陈雯雯
Owner 山西师范大学
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