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3a-(trifluoromethyl)-3,3a-dihydrobenzene[d]pyrrole[2,1-b]oxazole-1(2H)-ketone and synthesis method thereof

A technology of benzoxazole pyrrolidone and trifluoromethyl, applied in directions such as organic chemistry, can solve problems such as unreported, and achieve the effects of easy availability of raw materials and simple operation

Inactive Publication Date: 2009-09-30
SHANGHAI UNIV
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0005] The synthesis method of this compound has not been reported yet

Method used

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  • 3a-(trifluoromethyl)-3,3a-dihydrobenzene[d]pyrrole[2,1-b]oxazole-1(2H)-ketone and synthesis method thereof
  • 3a-(trifluoromethyl)-3,3a-dihydrobenzene[d]pyrrole[2,1-b]oxazole-1(2H)-ketone and synthesis method thereof
  • 3a-(trifluoromethyl)-3,3a-dihydrobenzene[d]pyrrole[2,1-b]oxazole-1(2H)-ketone and synthesis method thereof

Examples

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Effect test

Embodiment 1

[0031] Example 1: Preparation of 3a-(trifluoromethyl)-3,3a-dihydrobenzo[d]pyrrole[2,1-b]oxazol-1(2H)-one adopts the following steps: 1. in 50 ml Add 0.44 g of methyl trifluoro-γ-ketoate, 0.019 g of p-toluenesulfonic acid, 25 ml of toluene, and 0.2 g of anhydrous magnesium sulfate into a round-bottomed flask equipped with a reflux condenser. The above mixture was stirred and refluxed in an oil bath for half an hour, and then 0.218 g of o-aminophenol was added; ② The reactant gradually turned yellow under reflux. After 12 hours of reaction, 0.019 g of p-toluenesulfonic acid was added. The reaction was continued for 12 hours and then stopped. After the reaction was completed, anhydrous magnesium sulfate was removed by suction filtration, and the filtrate was concentrated. ③ The obtained concentrate was separated by silica gel chromatography, and the developer was a mixed solvent of petroleum ether and ethyl acetate with a volume ratio of 6:1 to obtain 0.35 g of a white solid wi...

Embodiment 2

[0032] Example 2: Preparation of 3a-(trifluoromethyl)-3,3a-dihydrobenzo[d]pyrrole[2,1-b]oxazol-1(2H)-one adopts the following steps: 1. in 250 ml Add 11 grams of methyl trifluoro-γ-ketoate, 0.475 grams of p-toluenesulfonic acid, 150 milliliters of toluene, and 8 grams of anhydrous magnesium sulfate in a round-bottomed flask equipped with a reflux condenser. The above mixture was stirred and refluxed in an oil bath for half an hour, and then 5.45 g of o-aminophenol was added; ② The reactant gradually turned yellow under reflux. After 12 hours of reaction, 0.475 g of p-toluenesulfonic acid was added. The reaction was continued for 16 hours and then stopped. After the reaction was completed, anhydrous magnesium sulfate was removed by suction filtration, and the filtrate was concentrated. ③ The obtained concentrate was separated by silica gel chromatography, and the developer was a mixed solvent of petroleum ether and ethyl acetate with a volume ratio of 6:1 to obtain 8.4 g of a...

Embodiment 3

[0033] Example 3: Preparation of 3a-(trifluoromethyl)-3,3a-dihydrobenzo[d]pyrrole[2,1-b]oxazol-1(2H)-one adopts the following steps: 1. in 2 liters Add 110 grams of methyl trifluoro γ-ketoate, 4.75 grams of p-toluenesulfonic acid, 1000 milliliters of toluene, and 25 grams of anhydrous magnesium sulfate in a round-bottomed flask equipped with a reflux condenser. The above mixture was stirred and refluxed in an oil bath for half an hour, and then 54.5 grams of o-aminophenol was added; ② The reactant gradually turned yellow under reflux. After 12 hours of reaction, 4.75 g of p-toluenesulfonic acid was added. The reaction was continued for 20 hours and then stopped. After the reaction was completed, anhydrous magnesium sulfate was removed by suction filtration, and the filtrate was concentrated. ③ The obtained concentrate was separated by silica gel chromatography, and the developer was a mixed solvent of petroleum ether and ethyl acetate with a volume ratio of 6:1 to obtain 81....

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Abstract

The invention relates to 3a-(trifluoromethyl)-3,3a-dihydrobenzene[d]pyrrole[2,1-b]oxazole-1(2H)-ketone and a synthesis method thereof. The structural formula of the compound is shown as right. The method comprises the following steps: dissolving trifluoro gamma-methyl keto ester and catalytic dosage of paratoluenesulfonic acid into toluene, adding catalytic dosage of anhydrous magnesium sulfate, carrying out reflux reaction on the mixture for 20 to 60 minutes with stirring, and then adding ortho-aminophenol; adding the catalytic dosage of paratoluenesulfonic acid after reacting for 10 to 15 hours, performing reflux reaction for 10 to 15 hours, and ending the reaction; and performing separation and purification to obtain a white solid, namely 3'-trifluoromethyl-1-benzopyrrole ketopyrrolidine derivative. The 3a-(trifluoromethyl)-3,3a-dihydrobenzene[d]pyrrole[2,1-b]oxazole-1(2H)-ketone creatively introduces a fluoridebearing group of trifluoromethyl with electron absorbing function to 3a position of benzopyrrole ketopyrrolidine so as to enhance the activity and be favorable for absorbing. In the invention, raw materials are easy to obtain, the operation is simple, the product is synthesized by a one-pot method, the productivity is up to 71 percent, and the product is suitable to be produced on a large scale.

Description

Technical field: [0001] The present invention relates to a kind of 3'-trifluoromethyl-1-benzoxazole pyrrolidone derivative and its synthesis method, especially a kind of 3a-(trifluoromethyl)-3,3a-dihydrobenzo[ d] Pyrrol[2,1-b]oxazol-1(2H)-one and its synthesis method. Background technique: [0002] Heterocyclic compounds are the most active field in organic chemistry. Heterocyclic compounds are closely related to life science and material science. Amino acids, vitamins, nucleic acid bases and alkaloids that play an important role in human life activities all contain heterocyclic structures. The list of heterocyclic compounds useful as medicines is too numerous to mention. In addition, heterocyclic structures are contained in some pesticides, herbicides, dyes, plastics, etc. [0003] The benzoxazole ring system has certain medicinal properties and exists in a few drugs. In addition, it is also an important intermediate of dyes, pesticides, and medicines. Such organic comp...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D498/04
Inventor 郝健侯明华庄红伟万文蒋海珍
Owner SHANGHAI UNIV
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