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Method for synthesizing 1,2-disubstituted benzimidazoles with 3-hydroxy-2-naphthoic acid and titanocene dichloride

A technology of dichlorotitanocene and benzimidazole is applied in the field of synthesis of 1,2-disubstituted benzimidazole compounds, and can solve the problems of tedious post-treatment process, poor reaction selectivity, difficult preparation of catalysts, and the like, To achieve the effect of simple post-processing, cheap catalyst and low synthesis cost

Active Publication Date: 2021-10-01
SHAANXI NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Catalysts reported in the literature include oxalic acid, proline, zinc-proline, zinc chloride, Bi(OTf) 3 , Yb(OTf) 3 , In(OTf) 3 , Silica-supported sulfuric acid, lactic acid, CuI nanoparticles, TiO 2 Nanoparticles and some other acids, the main disadvantages of these methods are the use of expensive reagents, difficult catalyst preparation, long reaction time, narrow substrate range, cumbersome post-treatment process, poor reaction selectivity

Method used

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  • Method for synthesizing 1,2-disubstituted benzimidazoles with 3-hydroxy-2-naphthoic acid and titanocene dichloride
  • Method for synthesizing 1,2-disubstituted benzimidazoles with 3-hydroxy-2-naphthoic acid and titanocene dichloride
  • Method for synthesizing 1,2-disubstituted benzimidazoles with 3-hydroxy-2-naphthoic acid and titanocene dichloride

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0013] Synthesis of 1-Benzyl-2-phenyl-(1H)-benzimidazole

[0014]

[0015] Add 0.1081g (1mmol) o-phenylenediamine, 0.0025g (0.01mmol) titanocene dichloride, 224μL (2.2mmol) benzaldehyde, and 2mL ethanol to the reaction flask, stir at 30°C for 20min, and remove the ethanol by rotary evaporation under reduced pressure. Using silica gel as a stationary phase, ethyl acetate and petroleum ether as a developing solvent, 1-benzyl-2-phenyl-(1H)-benzimidazole was obtained by column chromatography with a yield of 95%. The spectral data of the product are: 1 H NMR (400MHz, CDCl 3 )δ:7.89(d,J=8.0Hz,1H),7.70(dd,J=7.6,1.8Hz,2H),7.45(d,J=7.2Hz,3H),7.36-7.28(m,4H), 7.25-7.18(m,2H),7.10(d,J=6.7Hz,2H),5.45(s,2H); 13 C NMR (101MHz, CDCl 3 )δ: 154.30, 143.10, 136.42, 136.09, 130.09, 129.35, 129.18, 128.89, 127.91, 126.88, 126.06, 123.22, 122.88, 119.99, 110.69, 48.49.

Embodiment 2

[0017] Synthesis of 1-(4-methylbenzyl)-2-p-tolyl-(1H)-benzimidazole

[0018]

[0019] In this example, the benzaldehyde in Example 1 was replaced with an equimolar amount of p-tolualdehyde, stirred at 40°C for 4 hours, and the other steps were the same as in Example 1 to obtain 1-(4-methylbenzyl)- 2-p-Tolyl-(1H)-benzimidazole, the yield was 80%. The spectral data of the product are: 1 H NMR (400MHz, CDCl 3 )δ: 7.92(d, J=8.0Hz, 1H), 7.64(d, J=7.9Hz, 2H), 7.36-7.29(m, 1H), 7.27(d, J=7.9Hz, 2H), 7.22( q,J=7.5,6.5Hz,2H),7.14(d,J=7.8Hz,2H),7.01(d,J=7.8Hz,2H),5.40(s,2H),2.42(s,3H), 2.35(s,3H); 13 C NMR (101MHz, CDCl 3 )δ: 154.25, 143.20, 139.91, 137.32, 136.09, 133.43, 129.63, 129.38, 129.10, 127.21, 125.84, 122.76, 122.46, 119.77, 110.47, 48.08, 21.36, 21.02.

Embodiment 3

[0021] Synthesis of 1-(4-methoxybenzyl)-2-(4-methoxyphenyl)-(1H)-benzimidazole

[0022]

[0023] In this example, the benzaldehyde in Example 1 was replaced by an equimolar amount of p-methoxybenzaldehyde, stirred at 50°C for 5 hours, and the other steps were the same as in Example 1 to obtain 1-(4-methoxybenzyl )-2-(4-methoxyphenyl)-(1H)-benzimidazole, its productive rate is 96%, and the spectral data of product is: 1 H NMR (400MHz, CDCl 3 )δ: 7.71(d, J=8.0Hz, 1H), 7.50(d, J=8.4Hz, 2H), 7.14(dt, J=7.9, 3.9Hz, 1H), 7.06(d, J=3.7Hz, 2H), 6.87(d, J=8.3Hz, 2H), 6.81(d, J=8.5Hz, 2H), 6.69(d, J=8.4Hz, 2H), 5.20(s, 2H), 3.66(s, 3H), 3.61(s, 3H); 13 C NMR (101MHz, CDCl 3 )δ: 160.83, 159.03, 154.05, 143.08, 136.02, 130.61, 128.37, 127.14, 123.12, 122.69, 122.47, 122.32, 119.56, 114.33, 114.12, 113.99, 110.462, 55.7

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Abstract

The invention discloses a method for synthesizing 1,2-disubstituted benzimidazole compounds with 3-hydroxy-2-naphthoic acid in cooperation with titanocene dichloride. The method uses o-phenylenediamine and aldehyde as raw materials, and ethanol or Methanol is used as a solvent, titanocene dichloride is used as a catalyst, and 3-hydroxy-2-naphthoic acid is supplemented to efficiently and selectively synthesize 1,2-disubstituted benzimidazoles. The method of the invention is simple in operation, less in catalyst consumption, high in atom economy, mild in reaction conditions, short in reaction time, high in product yield, environmentally friendly, and has excellent selectivity for reaction products, and is useful for synthesizing 1,2-disubstituted benzene And imidazole compounds have broad application prospects.

Description

technical field [0001] The invention belongs to the technical field of synthesis of 1,2-disubstituted benzimidazole compounds, and specifically relates to a synthesis of 1,2-disubstituted benzimidazoles using titanocene dichloride and 3-hydroxy-2-naphthoic acid as catalysts. Method for imidazoles. Background technique [0002] Benzimidazole derivatives, as substances with a special nitrogen-containing heterocyclic structure, have important applications in medicinal chemistry. Due to their unique pharmacological properties and biological activities, many drugs with benzimidazole as the core structure have been used in clinical and commercialized. Studies have shown that benzimidazole derivatives exhibit different biological activities against many viruses such as influenza virus, human cytomegalovirus, and HIV virus. In addition, they also have anti-ulcer, anti-cancer, anti-diabetic, anti-bacterial, anti-microbial, anti-hypertensive, anti-inflammatory, anti-convulsant, anti...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D235/18C07D405/14C07D409/14
CPCC07D235/18C07D405/14C07D409/14
Inventor 高子伟庄梦媛张伟强孙华明苏洁马富余
Owner SHAANXI NORMAL UNIV