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Synthesis method of 3-hydroxyl diazoester intermediate alkyne compound

A technology of hydroxydiazo ester group and synthesis method, which is applied in the direction of organic chemistry, etc., and can solve problems such as corrosion and difficult operation

Inactive Publication Date: 2016-08-24
HUBEI UNIV OF SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The existence of strong alkali has great corrosion on reaction instruments and equipment, and the ultra-low temperature limits the difficulty of operation

Method used

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  • Synthesis method of 3-hydroxyl diazoester intermediate alkyne compound
  • Synthesis method of 3-hydroxyl diazoester intermediate alkyne compound
  • Synthesis method of 3-hydroxyl diazoester intermediate alkyne compound

Examples

Experimental program
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Effect test

Synthetic example 1

[0027] Synthesis of 3-Hydroxydiazoacetate Ethylphenylacetylene Compounds

[0028] Add 20 mol% K to the reaction vessel 2 CO 3 , 0.2mmol phenylpropynaldehyde, then add 1ml N,N-dimethylformamide, 0.2mmol ethyl diazoacetate, react at 25°C, after the reaction, wash with water, then extract with organic solvent, dry, and distill under reduced pressure The solvent was removed by concentration, and the crude product was separated by column chromatography to obtain the target product with a yield of 45%.

Synthetic example 2

[0030] Synthesis of 3-Hydroxydiazoacetate ethyl p-methylphenylacetylene compound

[0031] Add 50mol% triethylamine, 0.2mmol p-tolylpropynaldehyde to the reaction vessel, then add 1ml acetonitrile, 0.24mmol ethyl diazoacetate, and react at 40°C. After the reaction, wash with water, and then wash with organic solvent Extraction, drying, distillation and concentration under reduced pressure to remove the solvent, the crude product was separated by column chromatography to obtain the target product with a yield of 61%.

Synthetic example 3

[0033] Synthesis of 3-Hydroxydiazoacetate ethyl p-chlorophenylacetylene compound

[0034] Add 100 mol% CS to the reaction vessel 2 CO 3 , 0.2mmol p-bromophenylpropynaldehyde, then add 1ml 1,4-dioxane, 0.3mmol ethyl diazoacetate, react at 60°C, after the reaction, wash with water, then extract with organic solvent, dry, reduce Pressure distillation concentrated to remove the solvent, and the crude product was separated by column chromatography to obtain the target product with a yield of 45%.

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Abstract

The invention provides a synthesis method of a 3-hydroxyl diazoester intermediate alkyne compound. The synthesis method comprises the following steps: with a diazoacetate compound and various kinds of substituted propiolaldehyde as raw materials, synthesizing the 3-hydroxyl diazoester intermediate alkyne compound in a mild alkaline environment. The synthesis method provided by the invention has the advantages of simple operation, mild reaction conditions, cheap and available raw materials, wide reaction substrate adaptability, high product selectivity and yield, environmental friendliness and the like and has a good industrial application prospect.

Description

【Technical field】 [0001] The invention relates to the field of organic synthesis, in particular to a method for synthesizing a 3-hydroxydiazo ester-based intermediate alkyne compound. 【Background technique】 [0002] 3-Hydroxydiazoester-based intermediate alkyne compounds have important chemical properties due to their unique structure, and alkyne-containing compounds are widely found in natural products, synthetic drugs and agricultural chemicals. These compounds have good biological activity and pharmaceutical activity. Compounds containing intermediate alkynes can also be widely used in the field of materials. In addition, the 3-hydroxydiazo ester-based intermediate alkyne compound also has an ester functional group, which is also widely used in the field of synthesis. The diazo group can also be used as an important leaving group in a specific environment, so the 3-hydroxydiazo ester Alkyne compounds are a very important class of synthetic intermediates, which can be us...

Claims

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Application Information

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IPC IPC(8): C07C245/18C07D333/24C07D213/55
CPCC07C245/18C07D213/55C07D333/24
Inventor 孙绍发蒋龙强陈秀玲汪舰郭海兵
Owner HUBEI UNIV OF SCI & TECH
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