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1,2,5-multi-substituted imidazole derivatives and their synthesis method and application

A synthesis method and imidazole technology are applied in the field of 1,2,5-polysubstituted imidazole derivatives and their synthesis, which can solve the problems of insufficient substrate use range, poor regioselectivity, and difficulty in obtaining raw materials, and achieve high atomic The effect of economy, low catalyst dosage and wide substrate versatility

Active Publication Date: 2021-12-03
PINGDINGSHAN UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] At present, although the synthesis methods of related 1,2,5-multi-substituted imidazole structures have been reported, there are disadvantages such as unavailable raw materials, insufficient range of substrates, cumbersome operations, and poor regioselectivity.

Method used

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  • 1,2,5-multi-substituted imidazole derivatives and their synthesis method and application
  • 1,2,5-multi-substituted imidazole derivatives and their synthesis method and application
  • 1,2,5-multi-substituted imidazole derivatives and their synthesis method and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0032] The structure of the 1,2,5-multi-substituted imidazole derivatives of the present invention is shown in formula (1):

[0033] (1)

[0034] Among them, R 1 is phenyl, C 1 -C 10 Alkyl-substituted phenyl, halogen-substituted phenyl, C 1 -C 10 Alkoxy-substituted phenyl, naphthyl, furyl, thienyl; R 2 is phenyl, C 1 -C 10 Alkyl-substituted phenyl, halogen-substituted phenyl, C 1 -C 10 Alkoxy-substituted phenyl, naphthyl, pyrrolyl, furyl, thienyl; R 3 is phenyl, C 1 -C 10 Alkyl-substituted phenyl, halogen-substituted phenyl, C 1 -C 10 Alkoxy substituted phenyl, naphthyl, thienyl.

[0035] Preferably, the R 1p-methylphenyl, p-chlorophenyl, p-bromophenyl, p-methoxyphenyl, 3,5-dichlorophenyl, 3,5-dimethylphenyl, m-bromophenyl, m-methylphenyl Oxyphenyl, o-methoxyphenyl, o-benzyloxyphenyl, o-fluorophenyl, 2-naphthyl, 2-pyrrolyl, 2-furyl, 2-thienyl; R 2 p-methylphenyl, p-chlorophenyl, p-bromophenyl, p-methoxyphenyl, 3,5-dichlorophenyl, 3,5-dimethylphenyl, m-bromo...

Embodiment 2

[0037] The synthesis method of 1,2,5-multi-substituted imidazole derivatives of the present invention uses styryl azide, aromatic aldehyde, and aromatic amine as raw materials, uses rhodium acetate and phosphoric acid as catalysts, and uses organic solvents as solvents to undergo a one-step reaction , to obtain the 1,2,5-multi-substituted imidazole derivatives; the reaction process is shown in the reaction formula (I):

[0038] (I)

[0039] Put the styryl azide, aromatic aldehyde, aromatic amine, rhodium acetate, and phosphoric acid in a reaction flask, then add an organic solvent to form a mixed solution, and react by heating to obtain the 1,2,5-polysubstituted Imidazole derivatives;

[0040] The phosphoric acid is a racemic phosphoric acid containing a binaphthol skeleton, as shown in formula (2):

[0041] (2).

[0042] The molar ratio of the raw materials is styryl azide compound: aromatic aldehyde: aromatic amine: rhodium acetate: phosphoric acid = (2.0-3.0): (1.0-...

Embodiment 3

[0047] The synthesis method of the 1,2,5-multi-substituted imidazole derivatives of this embodiment is different from that of Example 2 in that the molar ratio of the raw materials is styryl azide compound: aromatic aldehyde: aromatic amine: rhodium acetate : phosphoric acid=2.0:1.0:1.0:0.02:0.1.

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Abstract

The invention relates to the technical fields of synthetic medicine and chemical industry, in particular to a 1,2,5-multi-substituted imidazole derivative and its synthesis method and application. A 1,2,5-multi-substituted imidazole derivative, the structure of which is shown in the formula: wherein, R1 or R2 is phenyl, C1-C10 alkyl substituted phenyl, halogen substituted phenyl, C1-C10 Any one of alkoxy substituted phenyl, naphthyl, pyrrolyl, furyl and thienyl; R3 is phenyl, C1‑C10 alkyl substituted phenyl, halogen substituted phenyl, C1‑ Any one of C10 alkoxy-substituted phenyl, naphthyl and thienyl. The synthesis method of the 1,2,5-multi-substituted imidazole derivatives of the present invention has the advantages of high atom economy, high regioselectivity, cheap and easy-to-obtain raw materials, low catalyst consumption, simple and safe operation, and the like. Synthesized multi-substituted imidazole derivatives widely exist in marketed drug molecules and are important pharmaceutical intermediates.

Description

technical field [0001] The invention belongs to the fields of synthetic medicine and chemical industry, and in particular relates to a 1,2,5-multi-substituted imidazole derivative and its synthesis method and application. Background technique [0002] As an important class of pharmacophore, imidazole organic compounds have been widely used in medicinal chemistry and pesticide chemistry, especially in antifungal, antifungal, and treatment of trichomoniasis. Among them, the drug activity of 1,2,5-polysubstituted imidazoles is particularly prominent. For example, metronidazole and tinidazole, which are commonly used in the treatment of oral anaerobic bacteria, are both 1,2,5-polysubstituted imidazoles. Therefore, as an important class of pharmacophore, 1,2,5-multi-substituted imidazoles have great application potential in drug development. Therefore, the synthesis of 1,2,5-multi-substituted imidazole structures has always been a research hotspot for workers in organic synthesi...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D233/58C07D233/64C07D233/56C07D405/04C07D409/04
CPCC07D233/56C07D233/58C07D233/64C07D405/04C07D409/04
Inventor 李玖零郑新华白现广王福安夏西超陈秋李钦贾欣宇陈娟王敏郭佳康杨玉洁张依雯
Owner PINGDINGSHAN UNIVERSITY
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