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Method for synthesizing benzimidazole and derivative

A technology for the synthesis of benzimidazole and its derivatives, which can solve problems such as incompatibility and practical offset, and achieve short reaction time, good functional group tolerance, and excellent yield. effect with purity

Inactive Publication Date: 2019-01-25
CHONGQING MEDICAL UNIVERSITY
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, the practicability of these methods is offset by special reactors and stoichiometric catalysts
Recently, Sun proposed a new scheme using 4 equivalents of phenyl silicon (PhSiH3) as a cocatalyst for the synthesis of benzimidazoles (Zhu J, Zhang Z, Miao C, Liu W, Sun W. Tetrahedron.2017:73 :3458.), but it turns out that this synthetic method is incompatible when extended to substrates containing electron-donating groups

Method used

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  • Method for synthesizing benzimidazole and derivative
  • Method for synthesizing benzimidazole and derivative
  • Method for synthesizing benzimidazole and derivative

Examples

Experimental program
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Embodiment 1

[0050] The general method of embodiment 1 synthetic benzimidazole derivatives (2a-3e)

[0051] Add 1a (0.54 g, 5 mmol), imidazole hydrochloride (0.09 g, 0.5 mmol) and 2 mL of N,N-dimethylformamide into a 10 mL three-neck round flask. The resulting solution was warmed to 120° C. and stirred at this temperature for reaction, followed by TLC plate detection. When the reaction was complete, 25 mL of water was added, and the resulting mixture was extracted twice with 25 mL of ethyl acetate. The combined organic layers were washed sequentially with H 2 O (50 mL), then brine (50 mL), then dried over anhydrous Na 2 SO 4 , filtered and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel and recrystallized from petroleum ether and ethyl acetate or petroleum ether / EA to give the desired product.

[0052] General method for the synthesis of benzimidazole derivatives (3f-3j)

[0053] A mixture of 1a (0.54 g, 5 mmol), imidazole hydrochlorid...

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Abstract

The invention provides a method for synthesizing benzimidazole and its derivative. The synthesis of polyfunctional benzimidazole and 2-substituted benzimidazole is achieved by imidazole chloride catalyzed o-phenylenediamine cyclization. The method is simple and economical and strong in practicability. No catalyst or additive is added. The synthesis method has good functional group tolerance, excellent yield and purity and short reaction time, does not require harsh reaction conditions and is suitable for industrial production.

Description

technical field [0001] The invention relates to benzimidazole and derivatives thereof, in particular to a synthesis method of benzimidazole and derivatives thereof. Background technique [0002] Benzimidazoles are a class of benzoheterocyclic compounds containing two nitrogen atoms, which are the structural units of various drugs. Many benzimidazole compounds have significant biological activity, and have important medical value in antitumor, anticancer, antiviral, bactericidal, anti-inflammatory and antiparasitic aspects. At the same time, benzimidazole compounds can also be used in the fields of corrosion inhibitors, transition metal ligands, simulating natural superoxidase (SOD) biological activities, surface active treatment agents, new curing agents for epoxy resins, and chemiluminescence. The traditional synthesis methods of benzimidazole compounds are mainly divided into two types, one is prepared by reacting o-phenylenediamine and its derivatives with carboxylic aci...

Claims

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Application Information

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IPC IPC(8): C07D235/06C07D235/02C07D235/08C07D235/18C07D401/04
CPCC07D235/02C07D235/06C07D235/08C07D235/18C07D401/04
Inventor 袁建勇田青强罗雯李丹代泽树王华均王雪桐
Owner CHONGQING MEDICAL UNIVERSITY
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