Polysubstitution imidazole calixarene derivative and preparation method thereof

A technology of arene derivatives and derivatives, applied in organic chemistry and other fields, can solve problems that cannot satisfy researchers' research on the application performance of calixarene derivatives, and achieve the effect of novel structure, fewer steps, and easy post-processing

Inactive Publication Date: 2013-06-05
QIQIHAR UNIVERSITY
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0005] The purpose of the present invention is to overcome the contradiction that the structure of the existing single imidazolium calixarene derivative cannot satisfy the researcher's research on the application performance of the calixarene derivative, and provide a structure of a multi-substituted imidazole calixarene derivative and preparation method

Method used

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  • Polysubstitution imidazole calixarene derivative and preparation method thereof
  • Polysubstitution imidazole calixarene derivative and preparation method thereof
  • Polysubstitution imidazole calixarene derivative and preparation method thereof

Examples

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Effect test

example 1

[0021] Example 1: Preparation of Polysubstituted Imidazocalixarene Derivative 1

[0022] (5,17-Di-tert-butyl-11,23-bis(2,4,5-triphenylimidazolyl)-25,27-dibutoxycalix[4]arene)

[0023] Diaminocalixarene derivative (5.0 mmol), benzil (7.5 mmol), benzaldehyde (5.0 mmol) and ammonium acetate (5.0 mmol) were added to 100 mL of acetic acid, and the temperature was slowly raised to 120 °C for 10 hours. After the reaction is completed, add about ice water while still hot, stir rapidly, use 5% NaOH solution to adjust the pH value of the reaction system between 7 and 8, and precipitate a large amount of solid; after filtration, the solid is dissolved in dichloromethane, and saturated brine is used. The organic phase was washed 2-3 times and dried over anhydrous magnesium sulfate overnight. The drying agent was filtered off and the organic phase was concentrated to give the crude product as a dark red oil. The crude product was recrystallized from chloroform to obtain 5,17-di-tert-buty...

example 2

[0024] Example 2: Preparation of polysubstituted imidazole calixarene derivatives 2

[0025] (5,17-Di-tert-butyl-11,23-bis(4,5-diphenyl-2-p-chlorophenylimidazolyl)-25,27-dibutoxycalix[4]arene)

[0026] Diaminocalixarene derivative (5.0 mmol), benzil (8.0 mmol), p-chlorobenzaldehyde (6.0 mmol) and ammonium acetate (7.5 mmol) were added to the reaction 100 mL of formic acid, and the temperature was slowly raised to 100 °C for reaction 12 Hour. After the reaction is completed, add about ice water while still hot, stir rapidly, use 5% NaOH solution to adjust the pH value of the reaction system between 7 and 8, and precipitate a large amount of solid; after filtration, the solid is dissolved in dichloromethane, and saturated brine is used. The organic phase was washed 2-3 times and dried over anhydrous magnesium sulfate overnight. The drying agent was filtered off and the organic phase was concentrated to give the crude product as a dark red oil. The crude product was recrystall...

example 3

[0027] Example 3: Preparation of multiple substituted imidazolium calixarene derivatives 3

[0028] (5,17-di-tert-butyl-11,23-bis(4,5-diphenyl-2-p-methoxyphenylimidazolyl)-25,27-dibutoxycalix[4]arene)

[0029] Diaminocalixarene derivative (5.0 mmol), benzil (10.0 mmol), p-methoxybenzaldehyde (10.0 mmol) and ammonium acetate (10.0 mmol) were added to the reaction 100 mL of isopropanol, and the temperature was slowly raised to 80 °C, react for 12 hours. After the reaction is over, add about ice water while it is hot, stir quickly, adjust the pH value of the reaction system between 7 and 8 with 5% NaOH solution, and precipitate a large amount of solids; The organic phase was washed 2-3 times, and dried overnight with anhydrous magnesium sulfate. The desiccant was filtered off, and the organic phase was concentrated to obtain a dark red oily crude product. The crude product was recrystallized from acetonitrile to obtain 5,17-di-tert-butyl-11,23-bis(4,5-diphenyl-2-p-methoxypheny...

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Abstract

The invention relates to a polysubstitution imidazole calixarene derivative and a preparation method thereof. The structure of the kind of compound is as follows. The polysubstitution imidazole calixarene derivative is novel in structure and overcomes the defect, of being single in structure, of imidazole calixarene. The provided compound is prepared by four groups including diamino [4] calixarene derivatives, o-dicarbonyl compounds, aldehydes and ammonium acetate in a one-step method. The method is simple, raw materials are easy to obtain, steps are few, post treatment is easy, operation is simple, the generation rate is high and the polysubstitution imidazole calixarene derivative and the preparation method thereof are suitable for industrial manufacture.

Description

technical field [0001] The invention relates to a structure of a polysubstituted imidazole calixarene derivative and a preparation method of the polysubstituted imidazole calixarene derivative. Background technique [0002] As the third-generation supramolecular host compound, calixarene has attracted the attention of many researchers due to its unique "cavity" structure and recognition performance. The functional modification of calixarene is an important topic in the study of calixarene host compounds. Designing and constructing calixarene derivatives with specific functional groups and cavity structures is the first step in the study of calixarene properties. Imidazoles are a class of small-molecule five-membered heterocyclic compounds containing two N atoms, which are important structural fragments of many biomolecules. Its bare N atom makes imidazole interact with specific guest molecules in different ways, so as to realize the recognition of imidazole to guest molecul...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D233/60C07D233/64
Inventor 赵冰阮耀宇阚伟王丽艳邓启刚
Owner QIQIHAR UNIVERSITY
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