Novel method for synthesizing oxazole compound

A synthesis method and technology for synthesizing oxazole, applied in the direction of organic chemistry and the like, can solve the problems of long reaction time, low yield, expensive reaction raw material catalyst, etc., and achieve the effects of simple operation, good yield and mild conditions

Inactive Publication Date: 2017-05-31
GUANGXI NORMAL UNIV
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Problems solved by technology

[0003] But at present, the method for synthesizing oxazole compound has the shortcoming that reaction time is long, and productive rate is lower, and reaction raw material catalyst is comparatively expensive.

Method used

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  • Novel method for synthesizing oxazole compound
  • Novel method for synthesizing oxazole compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0024] Synthesis of (2,4-diphenyl-5-oxazolyl)phenylphenone:

[0025] Add 30% (6.7 mg) copper bromide, 0.1 mmol (31.3 mg) 3-(benzylamino)-1,3-diphenylprop-2-en-1-one in 3 mL DMF solution to the flask, in oxygen React at 80°C for 2 h in the atmosphere; after the raw materials are consumed, cool to room temperature, remove the solvent by suction filtration under reduced pressure, and then purify by silica gel column chromatography (ethyl acetate:petroleum ether=1:100) to obtain light yellow Solid compound 4a 23.48 mg, yield rate 75%, its structural formula is, ;

[0026] 1 H NMR (400 MHz, CDCl 3 ) δ 8.13 – 8.10 (m, 2H), 8.02 (ddd, J = 5.4, 2.9, 1.5 Hz, 2H), 7.89 (dd, J = 8.4, 1.3 Hz, 2H), 7.52 (d, J = 7.4 Hz, 1H), 7.48 –7.44 (m, 3H), 7.42 – 7.39 (m, 2H), 7.35 (dd, J = 5.1, 1.8 Hz, 3H). 13 C NMR (100 MHz, CDCl 3 ) δ 183.19, 161.96, 148.84, 143.50, 137.58, 132.87, 131.75, 130.63, 129.84, 129.58, 129.32, 129.00, 128.36, 128.22, 127.435, 126.

Embodiment 2

[0028] Synthesis of (2-(4-methoxyphenyl)-4-phenyl-5-oxazolyl)phenylmethanone:

[0029] Add 30% (6.7 mg) copper bromide, 0.1 mmol (34.3 mg) 3-(3-methoxybenzyl)amino)-1,3-diphenylprop-2-en-1-one to the flask 3 mL of DMF solution was reacted at 80 °C for 2 h in an oxygen atmosphere; after the raw materials were consumed, cooled to room temperature, the solvent was removed by suction filtration under reduced pressure, and then purified by silica gel column chromatography (ethyl acetate:petroleum ether=1 : 100) to obtain 28.15 mg of orange solid compound 4b with a yield of 82%, and its structural formula is: ;

[0030] 1 H NMR (400 MHz, CDCl 3 ) δ 8.08 (dd, J = 6.5, 3.0 Hz, 2H), 7.95 (d, J =7.3 Hz, 2H), 7.74 (d, J = 7.7 Hz, 1H), 7.70 (d, J = 2.1 Hz, 1H), 7.55 (d, J =7.4 Hz, 1H), 7.46 (d, J = 7.8 Hz, 2H), 7.41 (ddd, J = 13.9, 8.5, 5.5 Hz, 5H),3.87 (s, 3H). 13 C NMR (100 MHz, CDCl 3 ) δ 183.09, 161.81, 159.99, 148.81, 143.52, 137.58, 132.95, 130.16, 129.90, 129.65...

Embodiment 3

[0032] Synthesis of (2-(4-fluorophenyl)-4-phenyl-5-oxazolyl)phenylmethanone:

[0033] Add 30% (4.1 mg) copper chloride, 0.1 mmol (33.1 mg) 3-((4-fluorobenzyl)amino)-1,3-diphenylprop-2-en-1-one in 3 mL of DMF solution was reacted at 80°C for 2 h in an oxygen atmosphere; after the raw materials were consumed, cooled to room temperature, the solvent was removed by suction filtration under reduced pressure, and then purified by silica gel column chromatography (ethyl acetate:petroleum ether=1 : 100) to obtain 22.28 mg of orange solid compound 4c with a yield of 67.3%, and its structural formula is: ;

[0034] 1 H NMR (400 MHz, CDCl 3 ) δ 8.21 – 8.15 (m, 2H), 8.08 – 8.03 (m, 2H), 7.95 – 7.91 (m, 2H), 7.61 – 7.55 (m, 1H), 7.46 (t, J = 7.7 Hz, 2H), 7.41 (dd, J =4.1, 2.5 Hz, 3H), 7.23 – 7.15 (m, 2H). 13 CNMR (400 MHz, CDCl 3 )δ 183.18, 166.20,163.68, 161.13, 148.81, 143.55, 137.54, 134.89, 132.93, 130.54, 129.91,129.80, 129.71, 129.56, 129.32, 129.04, 128.39, 128.26, 122.75,...

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Abstract

The invention discloses a novel method for synthesizing an oxazole compound. The novel method comprises the following steps: in the presence of oxygen, adding 0.1mmol of an enaminone compound and 30%mmol of a copper salt catalyst (such as copper bromide, copper chloride and cupric iodide) into a solvent (such as solutions of DMF (Dimethyl Formamide) and DMSO (Dimethylsulfoxide)), stirring to react for 2 hours at 80-100 DEG C, and tracking reaction with TLC (Thin-Layer Chromatography); and after the enaminone compound is completely consumed, cooling to the room temperature, performing depressurized sucking filtration to remove the solvent, and purifying by using silicagel column chromatography with ethyl acetate and petroleum ether in a ratio of 1:100, thereby obtaining a product. According to the novel method, the enaminone compound and oxygen are adopted as raw materials, C-H based activation is performed, and under the catalytic action of the copper salt, the oxazole compound can be synthesized by using a one-pot method. The novel method disclosed by the invention is easy in raw material obtaining, simple to operate, gentle in condition, good in yield and wide in application prospect.

Description

technical field [0001] The invention relates to the synthesis of oxazole compounds, in particular to a method for synthesizing oxazole compounds using enaminone compounds and oxygen as raw materials. Background technique [0002] Oxazole structures widely exist in natural products, active drugs and organic functional materials. These natural products and active drugs have very important medical value, and oxazole compounds are also very important industrial raw materials. [0003] But at present, the method for synthesizing oxazole compounds has the disadvantages of long reaction time, low yield, and relatively expensive reaction raw material catalysts. Contents of the invention [0004] The object of the present invention is to provide a new method for synthesizing oxazole compounds in one pot using enaminone compounds and oxygen as raw materials, based on C-H activation, and under the catalysis of copper salts. The method has easy-to-obtain raw materials, simple operati...

Claims

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Application Information

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IPC IPC(8): C07D263/32
CPCC07D263/32
Inventor 黄兵潘英明王恒山
Owner GUANGXI NORMAL UNIV
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