7-nitryl-3a-(trifluoromethyl)-2,3,3a,4-tetrahydrogen-1H-benzo(d) pyrrole (1,2-a) imidazole-1-ketone and synthesis method thereof

A technology of trifluoromethyl and p-toluenesulfonic acid, applied in the direction of organic chemistry, can solve the problems that have not been reported, and achieve high fat solubility and hydrophobicity, high drug efficacy, increased stability and physiological activity Effect

Inactive Publication Date: 2009-08-26
SHANGHAI UNIV
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  • Abstract
  • Description
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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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  • 7-nitryl-3a-(trifluoromethyl)-2,3,3a,4-tetrahydrogen-1H-benzo(d) pyrrole (1,2-a) imidazole-1-ketone and synthesis method thereof
  • 7-nitryl-3a-(trifluoromethyl)-2,3,3a,4-tetrahydrogen-1H-benzo(d) pyrrole (1,2-a) imidazole-1-ketone and synthesis method thereof
  • 7-nitryl-3a-(trifluoromethyl)-2,3,3a,4-tetrahydrogen-1H-benzo(d) pyrrole (1,2-a) imidazole-1-ketone and synthesis method thereof

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Experimental program
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Effect test

Embodiment 1

[0031] Embodiment 1: 1. add 0.44 grams of trifluoro γ-keto acid methyl esters, 0.019 grams of p-toluenesulfonic acid, 25 milliliters of toluene, 0.2 grams of anhydrous magnesium sulfate in 50 milliliters of round bottom flasks that reflux condenser tube is housed . The above mixture was stirred and refluxed in an oil bath for half an hour, and then 0.306 g of p-nitro-o-phenylenediamine was added; ② The reactant gradually turned dark red under reflux. After 12 hours of reaction, 0.019 g of p-toluenesulfonic acid was added. The reaction was continued for 24 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 2:1 to obtain 0.25 g of a yellow solid with a yield of 43%.

Embodiment 2

[0032] Embodiment 2: 1. add 11 grams of methyl trifluoro γ-keto acids in a 250 milliliter round-bottomed flask equipped with a reflux condenser, 0.475 grams of p-toluenesulfonic acid, 150 milliliters of toluene, and 5 grams of anhydrous magnesium sulfate . The above mixture was stirred and refluxed in an oil bath for half an hour, and then 7.65 g of p-nitro-o-phenylenediamine was added; ② The reactant gradually turned dark red under reflux. After 16 hours of reaction, 0.475 g of p-toluenesulfonic acid was added. The reaction was continued for 32 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 2:1 to obtain 5.87 g of a yellow solid with a yield of 41%.

Embodiment 3

[0033] Embodiment 3: 1. add 110 grams of trifluoro γ-keto acid methyl esters, 4.75 grams of p-toluenesulfonic acid, 1000 milliliters of toluene, 25 grams of anhydrous magnesium sulfate in 2 liters of round-bottomed flasks equipped with a reflux condenser . The above mixture was stirred and refluxed in an oil bath for half an hour, and then 76.5 g of p-nitro-o-phenylenediamine was added. ② The reactant gradually turned dark red under reflux. After 18 hours of reaction, 4.75 g of p-toluenesulfonic acid was added. The reaction was continued for 48 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 2:1 to obtain 56.1 g of a yellow solid with a yield of 39%.

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Abstract

The invention relates to a 7-nitryl-3a-(trifluoromethyl)-2,3,3a,4-tetrahydrogen-1H-benzo(d) pyrrole (1,2-a) imidazole-1-ketone and a synthesis method thereof. The compound has the following chemical formula: FORMULA (see the figure). The method comprises the following steps of: dissolving trifluoro Gamma-keto acid methyl ester and p-toluene sulfonic acid with catalyst dosage in toluene; adding in anhydrous magnesium sulfate with catalyst dosage; adding in 1,4-diaminobutane dihydrochloride after reflux reacting for 20-60 minutes under the condition of stirring; and adding in the p-toluene sulfonic acid with catalyst dosage after reacting for 10-15 h so as to finish the reaction; and separating and purifying to obtain yellow solid: 7-nitryl-3a-(trifluoromethyl)-2,3,3a,4-tetrahydrogen-1H-benzo(d) pyrrole (1,2-a) imidazole-1-ketone. The 7-nitryl-3a-(trifluoromethyl)-2,3,3a,4-tetrahydrogen-1H-benzo(d) pyrrole (1,2-a) imidazole-1-ketone has stronger activity and is more beneficial to being absorbed. The invention has the advantages of easy obtaining of raw materials, very simple operation, one-pot synthesis and productivity of 26% and is suitable for large-scale production.

Description

Technical field: [0001] The present invention relates to a 3'-trifluoromethyl-1-nitrobenzimidazole pyrrolone derivative and a synthesis method thereof, especially a 7-nitro-3a-(trifluoromethyl)-2, 3,3a,4-Tetrahydro-1H-benzo[d]pyrrole[1,2-a]imidazol-1-one and its synthesis method. Background technique: [0002] Heterocyclic compounds widely exist in nature and are the most numerous class of organic compounds. Many natural compounds contain heterocyclic ring systems, and these compounds often have strong physiological activities. In recent years, some artificially synthesized heterocyclic compounds have been widely used in pharmacy, materials science and other disciplines, and some heterocyclic compounds have been used in production as drugs, and have achieved good economic and social benefits. [0003] Pyrrolone compounds are a class of compounds with high application value. They are important pharmaceutical intermediates, used to produce Naofukang, Marylan, etc., and are a...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D487/04
Inventor 郝健侯明华庄红伟王静万文蒋海珍
Owner SHANGHAI UNIV
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