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Method for preparing alpha-aryl nitrile compound

A compound and aryl nitrile technology, applied in the field of preparing α-aryl nitrile compounds, can solve the problems of diversity of reaction substrates, limited scope of application, harsh reaction conditions, etc., and achieve easy products, mild reaction conditions and good selectivity. Effect

Active Publication Date: 2018-08-17
ZHEJIANG NORMAL UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, no matter which method is used, it faces many problems such as the diversity of reaction substrates, limited scope of application, and harsh reaction conditions.

Method used

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  • Method for preparing alpha-aryl nitrile compound
  • Method for preparing alpha-aryl nitrile compound
  • Method for preparing alpha-aryl nitrile compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0023]

[0024] N 2 Under protection, redistilled dichloromethane (5 mL) was added to a 25 ml reaction tube, then 161 mg (0.5 mmol) of iodobenzene diacetate was added, and then 180 microliters of trimethylsilyl trifluoromethanesulfonate was added (TMSOTf, 1.0mmol), the reaction solution was stirred at room temperature for 5min, and finally 198mg (0.6mmol) of α-tributyltin acetonitrile was added at -78°C, stirred for 5min, and the reaction progress was tracked by thin-layer chromatography. After the reaction was completed, saturated Sodium bicarbonate solution (3ml) quenched the reaction, slowly warmed to room temperature, then extracted with dichloromethane (3mL×3), the organic phase was dried over anhydrous sodium sulfate, concentrated in vacuo, and separated by column chromatography (Rf=0.19 , Developing agent: petroleum ether / ethyl acetate=40 / 1, v / v), the obtained product α-aryl nitrile compound is a white solid, and the yield is 86%.

[0025] The target product is char...

Embodiment 2

[0029]

[0030] N 2 Under protection, redistilled dichloromethane (5mL) was added to a 25ml reaction tube, then 161mg (0.5mmol) of iodobenzene diacetate was added, and then 180 microliters of TMSOTf (1.0mmol) was added, and the reaction solution was heated at room temperature Stir at low temperature for 5min, and finally add 223mg (0.6mmol) of α-tributyltinvaleronitrile at -78°C, stir for 5min, track the reaction progress with thin-layer chromatography, add saturated sodium bicarbonate solution (3ml) to quench the reaction after the reaction , slowly warming up to room temperature, then extracting with dichloromethane (3mL×3), the organic phase was dried over anhydrous sodium sulfate, concentrated in vacuo, separated by column chromatography (Rf=0.33, developing solvent: petroleum ether / ethyl acetate =40 / 1, v / v), the obtained product α-aryl nitrile compound was a yellow oil, and the yield was 77%.

[0031] The target product is characterized as follows:

[0032] 1 H NMR ...

Embodiment 3

[0035]

[0036] N 2 Under protection, redistilled dichloromethane (5mL) was added to a 25ml reaction tube, then 161mg (0.5mmol) of iodobenzene diacetate was added, and then 180 microliters of TMSOTf (1.0mmol) was added, and the reaction solution was heated at room temperature Stir for 5 minutes, and finally add 252 mg (0.6 mmol) of α-tributyltin phenylpropionitrile at -78 ° C, stir for 5 minutes, track the reaction process with thin-layer chromatography, add saturated sodium bicarbonate solution (3 ml) after the reaction is completed to quench reaction, slowly warming to room temperature, and then extracting with dichloromethane (3mL×3), the organic phase was dried over anhydrous sodium sulfate, concentrated in vacuo, and separated by column chromatography (Rf=0.27, developing solvent: petroleum ether / ethyl acetate Ester=40 / 1, v / v), the product obtained was a yellow oil with a yield of 69%.

[0037] The target product is characterized as follows:

[0038] 1 H NMR (600MHz...

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PUM

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Abstract

The invention discloses a method for preparing an alpha-aryl nitrile compound, and the method comprises rearrangement reaction of a diacetoxyl aryl iodide represented by the formula (I) and an alpha-tin-substituted nitrile compound represented by the formula (II) in the presence of trimethylsilyl trifluoromethanesulfonate to synthesize the alpha-aryl nitrile compound represented by the formula (III). The method has mild reaction conditions, good selectivity, high yield, easy separation of products and simple operation and other advantages.

Description

technical field [0001] The invention belongs to the field of organic chemical synthesis, in particular to a new method for preparing alpha-aryl nitrile compounds. Background technique [0002] The cyano group has good functional group derivatization and is a "star" group in the synthetic chemistry of drugs. Through simple hydrolysis or reduction reaction, the cyano group can be efficiently converted into carboxylic acid (Tetrahedron Lett.2014,55,3802-3804.), to prepare amides (Inorg.Chim.Acta.2005,358,1-21), (J.Org.Chem.1987,52,3901-3904.), aldehydes (Tetrahedron Lett.2002,43,1395-1396.) and amines (J.Med.Chem.1993,36,3300-3307.) compound. [0003] Among these cyano compounds, α-aryl nitrile compounds have attracted much attention, because α-aryl nitrile compounds widely exist in various natural product molecules, and are also important structural units in many drug molecules. For example, diphenoxylate: a drug used to treat diarrhea; anastrozole: a drug used to treat bre...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C253/30C07C255/35C07C255/37C07C255/41C07F7/18
CPCC07C253/30C07F7/1892C07C255/35C07C255/37C07C255/41
Inventor 黄鑫张亚鸽曾婷婷靳慧全许滢
Owner ZHEJIANG NORMAL UNIVERSITY
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