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A kind of preparation method of 2-substituted benzoxazole compound

A technology for benzoxazole and aldehyde compounds, which is applied in the field of preparation of 2-substituted benzoxazole compounds, and achieves the effects of cheap and easy-to-obtain raw materials, simple and easy operation, and high reaction efficiency

Inactive Publication Date: 2017-12-12
HENAN NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, although the above-mentioned synthetic methods have their own advantages, there are also certain shortcomings and deficiencies. Therefore, it is necessary to design a 2-substituted benzoxazole compound with high reaction efficiency and good reproducibility without adding additional additives. Preparation

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0014] Dissolve 109.2mg (1mmol) of o-aminophenol and 106.2mg (1mmol) of benzaldehyde in 3mL of xylene, heat up to 120°C for 1 hour, then cool down to room temperature, add 52mg (0.20mmol) of copper acetylacetonate, and pump negative pressure , reacted under an oxygen atmosphere, TLC monitored the completion of the reaction, concentrated the reaction system, and purified by column chromatography to obtain 186.6 mg of 2-phenylbenzoxazole, with a yield of 95.6%. 1 H NMR (400 MHz, CDCl 3 ): δ 7.34-7.38 (m, 2H), 7.52-7.54 (m, 3H), 7.57-7.61 (m, 1H), 7.76-7.81 (m, 1H), 8.25-8.29 (m, 2H); 13 C NMR (100MHz, CDCl 3 ): δ110.61, 120.04, 124.54, 125.13, 127.18, 127.64, 128.93, 131.54, 142.12,150.78, 163.06; m / z (ESI): 196 (M+H + ).

Embodiment 2

[0016] Dissolve 109.2mg (1mmol) of o-aminophenol and 106.2mg (1mmol) of benzaldehyde in 3mL of toluene, heat up to 100°C for 1 hour, cool down to room temperature, add 52mg (0.20mmol) of copper acetylacetonate, pump negative pressure, oxygen The reaction was carried out under the atmosphere, and the reaction system was concentrated after monitoring the completion of the reaction by TLC, and purified by column chromatography to obtain 168.3 mg of 2-phenylbenzoxazole, with a yield of 86.2%. 1 HNMR (400 MHz, CDCl 3 ): δ 7.34-7.38 (m, 2H), 7.52-7.54 (m, 3H), 7.57-7.61 (m,1H), 7.76-7.81 (m, 1H), 8.25-8.29 (m, 2H); 13 C NMR (100 MHz, CDCl 3 ): δ 110.61,120.04, 124.54 , 125.13, 127.18, 127.64, 128.93, 131.54, 142.12, 150.78,163.06; m / z(ESI): 196 (M+H + ).

Embodiment 3

[0018] Dissolve 109.2mg (1mmol) of o-aminophenol and 106.2mg (1mmol) of benzaldehyde in 3mL of DMSO, heat up to 120°C for 1 hour, cool down to room temperature, add 52mg (0.20mmol) of copper acetylacetonate, pump negative pressure, oxygen The reaction was carried out under atmosphere, and the reaction system was concentrated after monitoring the completion of the reaction by TLC, and purified by column chromatography to obtain 30.5 mg of 2-phenylbenzoxazole, with a yield of 15.6%. 1 HNMR (400 MHz, CDCl 3 ): δ 7.34-7.38 (m, 2H), 7.52-7.54 (m, 3H), 7.57-7.61 (m,1H), 7.76-7.81 (m, 1H), 8.25-8.29 (m, 2H); 13 C NMR (100 MHz, CDCl 3 ): δ 110.61,120.04, 124.54 , 125.13, 127.18, 127.64, 128.93, 131.54, 142.12, 150.78,163.06; m / z(ESI): 196 (M+H + ).

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Abstract

The invention discloses a method for preparing a 2-substituted benzoxazole compound, and belongs to the technical field of synthesis of benzoxazole compounds. According to the technical scheme, the method is characterized by comprising the steps that an aldehyde compound R1CHO and an ortho-aminophenol compound (please see the specification for the formula) are dissolved in solvent xylene or methylbenzene, and pre-reacting is conducted for one hour when the solvent is heated to be at the temperature of 120 DEG C; then the temperature is lowered to be an indoor temperature, catalyst copper acetylacetonate is added, and negative pressure suction is carried out in the oxygen atmosphere for reacting till TLC monitors that the reacting is complete; filtering is performed, and water and ethyl acetate are added in filter liquor to be extracted; an organic phase is dried through anhydrous sodium sulfate, column chromatography purification is carried out after the solvent is removed by steaming, and accordingly the 2-substituted benzoxazole compound (please see the specification for the formula) is obtained. According to the method, the aldehyde compound and the ortho-aminophenol compound are used as reacting raw materials, the copper acetylacetonate is used as a catalyst, oxygen is used as an oxidizing agent, no extra additives are needed, and a series of 2-substituted benzoxazole compounds are synthesized; operation is simple and practicable, the raw materials are cheap and easy to get, reaction efficiency is high and repeatability is good.

Description

technical field [0001] The invention belongs to the technical field of synthesis of benzoxazole compounds, in particular to a preparation method of 2-substituted benzoxazole compounds. Background technique [0002] Among the organic compounds that exist in nature, there is a large class of compounds containing heteroatom ring structures, namely heterocyclic compounds. These compounds exist in a variety of organisms and play a vital role in the maintenance and metabolism of organisms. The nitrogen heterocyclic organic compounds play a pivotal role in the heterocyclic compounds. Because these compounds have important applications in many fields, organic chemists are constantly exploring new methods of synthesizing them. Benzoxazole compounds are benzo heterocyclic compounds containing nitrogen atoms and oxygen atoms in their molecular structure. This type of compound exhibits good antibacterial, anti-inflammatory, and plant virus-killing effects and coordination properties. ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D263/57C07D413/04
CPCC07D263/57C07D413/04
Inventor 贾淑红张丹丹何兴王文丽姜玉钦董文佩徐桂清李伟
Owner HENAN NORMAL UNIV
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