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A kind of preparation method of 1,2-substituted benzimidazole derivatives

A technology of benzimidazoles and derivatives, applied in 1 field, can solve the problems of many side reactions and wastes, low atom utilization rate, unfriendly environment, etc., and achieves green post-treatment, small catalyst dosage, and reaction specificity. strong effect

Active Publication Date: 2019-08-06
HUAQIAO UNIVERSITY
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, there are many problems in these methods: 1) the use of halogenated substances is not friendly to the environment; 2) most of the reactions are multi-step reactions with low yield and low efficiency; 3) there are many side reactions and wastes, and the utilization rate of atoms is relatively low ; 4) The substrate is complex and difficult to obtain, etc.

Method used

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  • A kind of preparation method of 1,2-substituted benzimidazole derivatives
  • A kind of preparation method of 1,2-substituted benzimidazole derivatives
  • A kind of preparation method of 1,2-substituted benzimidazole derivatives

Examples

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Effect test

Embodiment 1

[0021] Preparation of 2-phenyl-1-p-toluenesulfonylbenzimidazole, Ts = p-toluenesulfonyl

[0022]

[0023] N-phenylbenzamidine 0.2mmol, p-toluenesulfonyl azide 0.3mmol, dichloro(pentamethylcyclopentadienyl) iridium (IIl) dimer 0.008mmol, bistrifluoromethanesulfonimide Add 0.032mmol of silver salt and 0.2mmol of phenylacetic acid to a test tube containing a stirring bar and add 2mL of 1,2-dichloroethane solvent, place in an oil bath at 80°C, react for 12h, remove the heat source from the reaction, and cool to room temperature . The reaction solution was concentrated and purified by column chromatography to obtain 75.9 mg of the target product with a yield of 97%. The NMR characterization of this compound is as follows: 1 H NMR (400MHz, CDCl3) δ8.20 (d, J = 7.3Hz, 1H), 7.72 (d, J = 7.9Hz, 1H), 7.61 (d, J = 7.8Hz, 2H), 7.54 (dd, J =11.2, 4.5Hz, 1H), 7.48-7.36(m, 4H), 7.32(d, J=8.2Hz, 2H), 7.09(d, J=8.2Hz, 2H), 2.32(s, 3H). 13 C NMR (101MHz, CDCl3) δ 154.03, 145.64, 142.61, ...

Embodiment 2

[0025] Preparation of 4-fluoro-2-phenyl-1-p-toluenesulfonylbenzimidazole, Ts = p-toluenesulfonyl

[0026]

[0027] N-(2-fluorophenyl)benzamidine 0.2mmol, p-toluenesulfonyl azide 0.3mmol, dichloro(pentamethylcyclopentadienyl) iridium(III) dimer 0.008mmol, bistrifluoro Add 0.032mmol of methanesulfonylimide silver salt and 0.2mmol of phenylacetic acid to a test tube containing a stirring bar and add 2mL of 1,2-dichloroethane solvent, place it in an oil bath at 80°C, and react for 12 h. Remove from heat and cool to room temperature. The reaction solution was concentrated and purified by column chromatography to obtain 47.2 mg of the target product, with a yield of 62%. The NMR characterization of this compound is as follows: 1 H NMR (400MHz, CDCl 3 )δ8.00(d, J=8.3Hz, 1H), 7.61(d, J=7.3Hz, 2H), 7.55(t, J=7.4Hz, 1H), 7.45(t, J=7.5Hz, 2H) , 7.36(td, J=8.3, 5.2 Hz, 1H), 7.31(d, J=8.2Hz, 2H), 7.09(t, J=7.6Hz, 3H), 2.32(s, 3H). 13 C NMR (101MHz, CDCl 3 )δ154.22, 153.65 (d, J=25...

Embodiment 3

[0029] Preparation of 4-bromo-2-phenyl-1-p-toluenesulfonylbenzimidazole, Ts = p-toluenesulfonyl

[0030]

[0031] N-(2-bromophenyl)benzamidine 0.2mmol, p-toluenesulfonyl azide 0.3mmol, dichloro(pentamethylcyclopentadienyl) iridium(III) dimer 0.008mmol, bistrifluoro Add 0.032mmol of methanesulfonylimide silver salt and 0.2mmol of phenylacetic acid to a test tube containing a stirring bar and add 2mL of 1,2-dichloroethane solvent, place it in an oil bath at 80°C, and react for 12 h. Remove from heat and cool to room temperature. The reaction solution was concentrated and purified by column chromatography to obtain 50.3 mg of the target product, with a yield of 60%. The NMR characterization of this compound is as follows: 1 H NMR (400MHz, CDCl 3 )δ8.18(d, J=8.3Hz, 1H), 7.60-7.56(m, 3H), 7.53(d, J=7.5Hz, 1H), 7.44(t, J=7.6Hz, 2H), 7.30( dt, J=8.0, 3.9 Hz, 3H), 7.10(d, J=8.3Hz, 2H), 2.33(s, 3H). 13 C NMR (101MHz, CDCl 3 )δ154.42, 146.02, 141.22, 134.69, 134.30, 131.01, 130...

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Abstract

The invention discloses a preparation method of a 1,2-substituted benzimidazole derivative. The preparation method comprises the following steps: uniformly mixing an N-phenyl amidine derivative, a nitrine derivative, an acid compound, a catalyst, a metal salt and an organic solvent; and performing a reaction for 10-13h at 78-82 DEG C in an air atmosphere to obtain the 1,2-substituted benzimidazole derivative. The method disclosed by the invention can be used for synthesizing a compound with a benzimidazole derivative framework, which cannot be synthesized by other methods. The used raw materials are easily available, and the preparation method is high in yield, mild in reaction condition, wide in primer range, small in catalyst dosage, strong in reaction specificity and simple and green in post-treatment, and the utilization ratio of atoms reaches up to 90% and above.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis, and in particular relates to a preparation method of 1,2-substituted benzimidazole derivatives. Background technique [0002] Benzimidazole derivatives are a class of nitrogen-containing heterocyclic organic compounds with a wide range of uses, and have important application values ​​in natural products, biomedicine, pesticides, ligands, and organic synthesis. They have a variety of physiological activities (such as: anti-inflammatory, antispasmodic, antihistamine, anti-cancer, inhibition of cyclooxygenase, HIV-1 reverse transcriptase inhibitor, etc.) and clinical applications, etc., have been favored by many scientists . Therefore, the research on new synthesis methods of multi-substituted benzimidazole derivatives has important application value and has attracted the attention of researchers in related fields. [0003] The traditional method of synthesizing benzimidazole derivatives...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D235/08C07D235/18C07D235/02
CPCC07D235/02C07D235/08C07D235/18
Inventor 崔秀灵徐林华
Owner HUAQIAO UNIVERSITY
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