Method for preparing indole-2,3-dione derivatives by catalytic oxidation of microwave copper/peroxyacetic acid
A technology of peracetic acid catalyzing indium oxide and peracetic acid, applied in the direction of organic chemistry and the like, can solve the problems of safety of reagents, difficulty in obtaining raw materials, severe reaction conditions, etc., and achieves the effects of simple operation, environmental friendliness and simple operation.
Inactive Publication Date: 2018-08-10
FUJIAN MEDICAL UNIV
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Problems solved by technology
The currently reported methods for synthesizing benzindole isatin derivatives have their own advantages and disadvantages. More or less due to the difficulty in obtaining raw materials, some reagents have potential safety hazards, severe reaction conditions and low yields, etc., so simple, safe, and pollution-free methods are sought. Synthetic pathways are the preferred question
Method used
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Embodiment 1
[0028] Example 1: Indole-2,3-dione: 1 mmol of indole was added to the reaction vessel, followed by 0.05 mmol of cuprous iodide, 4 mmol of peracetic acid, and 3 ml of ethanol. It was placed in a microwave reactor and heated to 60 °C under 120 W for continuous reaction for 10 min. After the reaction was completed, it was cooled to room temperature, concentrated under reduced pressure, and the product was purified by column chromatography to obtain a red solid with a yield of 68%.
Embodiment 2
[0029] Example 2: 1-methylindole-2,3-dione: The preparation method was the same as that of Example 1, and 1 mmol of 1-methylindole was added to obtain a red solid with a yield of 65%.
Embodiment 3
[0030] Example 3: 1-ethylindole-2,3-dione: The preparation method was the same as that of Example 1, and 1 mmol of 1-ethylindole was added to obtain a red solid with a yield of 61%.
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The invention discloses a method for preparing indole-2,3-dione derivatives by catalytic oxidation of microwave copper / peroxyacetic acid. The method comprises the following steps: a catalytic amount of catalyst copper iodide, indole, a derivative of the indole and peroxyacetic acid are added into a reaction vessel, wherein the indole, the derivative of the indole and the peroxyacetic acid are usedas raw materials, ethanol is used as a solvent, the reaction vessel is placed into a microwave reaction instrument, a reaction is performed at certain temperature and power, after a certain time, reduced-pressure concentration is performed, and a product is purified by column chromatography. The method provided by the invention is a method having novel raw materials, simple operation and high efficiency used for preparing a benzimidazole derivative; and compared with the prior art, the method provided by the invention has an obviously-accelerated reaction speed than that under conventional heating, mild reaction conditions, simple operation, a high yield, safety, low costs and environmental protection.
Description
technical field [0001] The present invention relates to a method for the preparation of indole-2,3-dione derivatives. That is, using substituted indole and peracetic acid as raw materials, introducing microwave as auxiliary synthesis means, and efficiently catalyzing the rapid preparation of indole-2,3-dione derivatives. Background technique [0002] Indole-2,3-dione, also known as isatin, is an alkaloid with a relatively simple structure that is widely present in natural products. It is found in the roots and stems of Cao Daqing, a plant belonging to the genus family, and is also an important ingredient in the famous traditional Chinese medicine Indigo Naturalis. In addition, it is widely distributed in human organs, body fluids, especially in the hippocampus and other parts of the brain. Indole-2,3-dione and its derivatives have a variety of biological activities, and it is very meaningful to study their activities in anti-tumor, anti-virus, neuroprotection and so on. ...
Claims
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IPC IPC(8): C07D209/38
CPCC07D209/38
Inventor 林晨柯方许建华张鹏林小燕许贻文
Owner FUJIAN MEDICAL UNIV