1-(3-N-substituted-carbazolyl)-3-aryl-3-diacetyl methyne-acetone and preparation method thereof

A technology based on diacetyl methine and carbazolyl, applied in botany equipment and methods, chemicals for biological control, biocides, etc., can solve the problem of low reaction catalyst efficiency, long reaction time, and product yield Low-level problems, to achieve the effect of good catalytic effect, short reaction time and simple reaction process

Inactive Publication Date: 2017-07-18
SHAANXI UNIV OF SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The traditional Michael addition is a reflux method using methanol as a solvent, the reaction catalyst efficiency is low, the product yield is low, there are many by-products, and the reaction time is as long as 24h

Method used

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  • 1-(3-N-substituted-carbazolyl)-3-aryl-3-diacetyl methyne-acetone and preparation method thereof
  • 1-(3-N-substituted-carbazolyl)-3-aryl-3-diacetyl methyne-acetone and preparation method thereof
  • 1-(3-N-substituted-carbazolyl)-3-aryl-3-diacetyl methyne-acetone and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0042]Add 0.0055mol acetylacetone, 0.0055mol sodium hydroxide (solid, granular) and 30mL absolute ethanol in sequence to a 250mL dry three-neck flask equipped with a condensing reflux tube and a stirring device, stir at room temperature for about 5min, and mix well Finally, dissolve 0.001mol of 1-(3-N-methyl-carbazolyl)-3-p-chlorophenyl-propenone in 30mL of absolute ethanol, and use a dropper to slowly Add it dropwise into a three-necked flask. After the dropwise addition, slowly raise the temperature of the water bath to 80°C, keep the temperature at 80°C, stir at a constant speed of 70rad / min and react for 100min. The reaction progress was monitored by TLC, and a developer with a volume ratio of V (ethyl acetate): V (petroleum ether) = 1:5 was selected. After the reaction is complete, stop the reaction, let the reaction system drop to room temperature slowly, add 20mL of 3°C cold water, let it stand still, a solid precipitates, filter with suction, wash the filter cake repea...

Embodiment 2

[0048] Add 0.0055mol acetylacetone, 0.0055mol sodium hydroxide (solid, granular) and 30mL absolute ethanol in sequence to a 250mL dry three-neck flask equipped with a condensing reflux tube and a stirring device, stir at room temperature for about 5min, and mix well Finally, dissolve 0.001mol of 1-(3-N-methyl-carbazolyl)-3-phenyl-propenone in 30mL of absolute ethanol, and slowly add it dropwise with a dropper while stirring at a constant speed with a stirrer Put it into a three-neck flask, after the dropwise addition, slowly raise the temperature of the water bath to 80°C, keep the temperature at 80°C, stir at a constant speed of 70rad / min and react for 100min. The reaction progress was monitored by TLC, and a developer with a volume ratio of V (ethyl acetate): V (petroleum ether) = 1:5 was selected. After the reaction is complete, stop the reaction, let the reaction system drop to room temperature slowly, add 20mL of 3°C cold water, let it stand still, a solid precipitates, f...

Embodiment 3

[0052] Add 0.0055mol acetylacetone, 0.0055mol sodium hydroxide (solid, granular) and 30mL absolute ethanol in sequence to a 250mL dry three-neck flask equipped with a condensing reflux tube and a stirring device, stir at room temperature for about 5min, and mix well Finally, 0.001mol of 1-(3-N-methyl-carbazolyl)-3-(2-thienyl)-propenone was dissolved in 30mL of absolute ethanol, and the The tube was slowly added dropwise into the three-necked flask. After the dropwise addition, the temperature of the water bath was slowly raised to 80°C, and the temperature was maintained at 80°C. Stirring at a constant speed of 70rad / min and reacted for 100min. The reaction progress was monitored by TLC, and a developer with a volume ratio of V (ethyl acetate): V (petroleum ether) = 1:5 was selected. After the reaction is complete, stop the reaction, let the reaction system drop to room temperature slowly, add 20mL of 3°C cold water, let it stand still, a solid precipitates, filter with suctio...

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Abstract

The invention discloses 1-(3-N-substituted-carbazolyl)-3-aryl-3-diacetyl methyne-acetone and a preparation method thereof. The structural formula of the 1-(3-N-substituted-carbazolyl)-3-aryl-3-diacetyl methyne-acetone is as shown in the description. The preparation method comprises the following steps of: adding 1-(3-N-substituted-carbazolyl)-3-aryl-acrylketone, sodium hydroxide, acetylacetone and absolute ethyl alcohol into a reaction container; performing a heating reflux reaction under stirring; after reaction, adding a proper amount of cold water; leaving the mixture to stand for a while to separate out a solid; performing suction filtration; repeatedly washing the filter cake to neutral; recrystallizing the filter cake with absolute ethyl alcohol; and evaporating the solvent with a rotary evaporator and performing vacuum drying to obtain a target product. By selecting a cheap and easily available catalyst sodium hydroxide, the catalytic effect is good and side reactions are unlikely to happen. A classical reflux method is adopted, so that the preparation method is simple in post-treatment, high in yield and short in reaction time, and the prepared product has the functions of sterilizing, inhibiting bacteria, weeding and etc.

Description

technical field [0001] The invention belongs to the field of chemical synthesis, and particularly relates to 1-(3-N-substituted-carbazolyl)-3-aryl-3-diacetylmethine-acetone and a preparation method thereof. Background technique [0002] Carbazole is an important heterocyclic compound. The carbazole ring is easy to form a relatively stable positive ion. Drugs containing the core structure of carbazole compounds have been widely found in many natural plants. research interests of workers. It contains large conjugated system and strong electron transfer in the molecule, has strong electron donating ability and hole transport ability, and high thermal stability and photochemical stability; its derivatives are widely used in photoelectric materials, dyes, medicine, Supramolecular recognition, chemical sensing and other fields have a wide range of potential applications. More importantly, carbazole compounds are easy to carry out structural modification of functional groups, and...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D209/86C07D409/06C07D405/06A01N43/38A01P1/00A01P3/00A01P13/00A61P31/00
CPCA01N43/38C07D209/86C07D405/06C07D409/06
Inventor 尹大伟王雨薇刘玉婷黄涛吴倩倩辛宏刘一嘉盛娇
Owner SHAANXI UNIV OF SCI & TECH
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