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Method for synthesizing 1,2-disubstituted benzimidazole compounds from 3-hydroxy-2-naphthoic acid assisted with 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 difficult preparation of catalysts, tedious post-treatment process, poor reaction selectivity and the like, Achieve the effect of low synthesis cost, simple post-treatment and cheap catalyst

Active Publication Date: 2018-12-14
SHAANXI NORMAL UNIV
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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 benzimidazole compounds from 3-hydroxy-2-naphthoic acid assisted with titanocene dichloride
  • Method for synthesizing 1,2-disubstituted benzimidazole compounds from 3-hydroxy-2-naphthoic acid assisted with titanocene dichloride
  • Method for synthesizing 1,2-disubstituted benzimidazole compounds from 3-hydroxy-2-naphthoic acid assisted with 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 from 3-hydroxy-2-naphthoic acid assisted with titanocene dichloride. According to the method, o-phenylenediamine and aldehyde are used as raw materials, ethanol or methanol is used as a solvent, titanocene dichloride is used as a catalyst assisted with 3-hydroxy-2-naphthoic acid, and the 1,2-disubstituted benzimidazole compounds can be synthesized efficiently and selectively. The method provided by the invention is simple to operate, less in catalyst dosage, high in atomic economy, mild in reaction condition, short in reaction time, high in product yield, environmentally friendly, and excellent in selectivity for reaction products, and has broad application prospects for the synthesis of the 1,2-disubstituted benzimidazole compounds.

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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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
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