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Method for synthesizing 2,4,5-three substitutive imidazole ring derivative through enzyme catalysis

A synthesis method and technology of imidazole rings, which are applied in the field of synthesizing 2,4,5-trisubstituted imidazole ring derivatives, can solve the problems of complicated operation and severe reaction conditions, and achieve high reaction yield and mild reaction conditions , The effect of less discharge of three wastes

Inactive Publication Date: 2015-03-18
HANGZHOU NORMAL UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

These methods have disadvantages such as complicated operation and severe reaction conditions.

Method used

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  • Method for synthesizing 2,4,5-three substitutive imidazole ring derivative through enzyme catalysis
  • Method for synthesizing 2,4,5-three substitutive imidazole ring derivative through enzyme catalysis

Examples

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Embodiment 1

[0022] Embodiment 1: the synthesis of 2-(2-chloro-phenyl)-4,5-diphenyl-1H-imidazole

[0023] Add about 0.5mmol of benzil, about 0.5mmol of o-chlorobenzaldehyde, about 1.5mmol of ammonium acetate, 3mL of ethanol, about 0.035g of lipase (Lipase AT30) into a 10mL test tube, and shake the reaction at a temperature of 45°C After about 9 hours to the end of the reaction, the clear liquid was collected by centrifugation for precipitation, and the crude product was subjected to silica gel column chromatography (developing solvent: petroleum ether / ethyl acetate=5 / 1) to obtain 0.12 g of the compound, with a yield of 73%.

[0024] Product characterization: Mp: 197.2-197.5℃. IR(KBr) 3411, 2812, 1592, 1383, 1357, 1078, 764.1H NMR (400MHz, CDCl3), δ7.31-7.47(m, 10H), 7.53-7.67( m,4H).

Embodiment 2

[0025] Example 2: Synthesis of 2-(2-chloro-phenyl)-4,5-diphenyl-1H-imidazole

[0026] Add about 0.5mmol of benzil, about 0.5mmol of o-chlorobenzaldehyde, about 1.5mmol of ammonium acetate, 3mL of ethanol, and about 0.035g of α-Amylase from Aspergillus oryzae into a 10mL test tube. Shake the reaction at 45°C for about 9 hours until the end of the reaction, centrifuge the clear liquid to precipitate the solvent, and the crude product is subjected to silica gel column chromatography (developing solvent: petroleum ether / ethyl acetate=5 / 1) to obtain 0.075g of the compound with a yield of 45 %.

[0027] Product characterization: Mp: 197.2-197.5℃. IR(KBr) 3411, 2812, 1592, 1383, 1357, 1078, 764.1H NMR (400MHz, CDCl3), δ7.31-7.47(m, 10H), 7.53-7.67( m,4H).

Embodiment 3

[0028] Example 3: Synthesis of 2-(2-chloro-phenyl)-4,5-diphenyl-1H-imidazole

[0029] Add about 0.5mmol of benzil, about 0.5mmol of o-chlorobenzaldehyde, about 1.5mmol of ammonium acetate, 3mL of ethanol, and about 0.035g of α-Amylase from Aspergillus oryzae into a 10mL test tube. Shake the reaction at 30°C for about 9 hours until the end of the reaction, centrifuge the clear liquid to precipitate the solvent, and the crude product is subjected to silica gel column chromatography (developing solvent: petroleum ether / ethyl acetate=5 / 1) to obtain 0.098g of the compound with a yield of 60 %.

[0030] Product characterization: Mp: 197.2-197.5℃. IR(KBr) 3411, 2812, 1592, 1383, 1357, 1078, 764.1H NMR (400MHz, CDCl3), δ7.31-7.47(m, 10H), 7.53-7.67( m,4H).

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Abstract

The invention discloses a method for synthesizing 2,4,5-three substitutive imidazole ring derivative shown in a formula (I) through enzyme catalysis. The synthesis method comprises the step of reacting under enzyme catalysis action with dibenzoyl and R-CHO ammonium acetate as reactants in an organic solvent, so as to obtain the 2,4,5-three substitutive imidazole ring derivative, wherein the enzyme is selected from the following enzymes: lipase AT30, alpha-amylase from hog pancreas, diastase from aspergillus oryzae, trypsin NB from porcinepancreas and albumin from bovine. The method disclosed by the invention has mild conditions and higher yield and is environment-friendly.

Description

(1) Technical field [0001] The invention relates to a method for synthesizing 2,4,5-trisubstituted imidazole ring derivatives. (2) Background technology [0002] Imidazole and its derivatives have proton-accepting properties, conjugated acid-base properties, and complex coordination properties, and enjoy the reputation of "biocatalyst" and "bioligand". In nature, imidazole, as the active center functional group of many enzymes, participates in important biochemical reactions and plays a very important role in life activities. Many drugs, enzyme inhibitors, etc. also contain imidazole central functional group. At the same time, it is a common heterocyclic compound in natural products and medicines. It has a variety of biological activities and pharmacological activities. Its biological activities such as antibacterial, antiviral, and anti-inflammatory are very significant in medicine. It is also commonly used in epoxy resin curing (accelerator) agents. , urethane catalyst, ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C12P17/10C12P17/16
Inventor 郑辉施巧月杜奎梅怡嘉章鹏飞
Owner HANGZHOU NORMAL UNIVERSITY