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Method for green synthesis of norcantharidin derivative

A green synthesis technology of demethylcantharidin, applied in the direction of organic chemistry, can solve the problems of long reaction time, many reaction steps, high solvent toxicity, etc., and achieve good substrate adaptability, mild reaction conditions, and simple reaction steps Effect

Inactive Publication Date: 2017-01-25
YUNNAN MINZU UNIV
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Problems solved by technology

[0003] In order to solve the problems in the current synthesis of norcantharidin derivatives that there are many reaction steps, a wide variety of raw materials, long reaction time, low yield, and the toxicity of solvents in some methods, the invention provides a method for preparing norcantharidin derivatives The synthesis method of the compound is to prepare demethylcantharidin by furan and maleic anhydride at room temperature through the Diels-Alder reaction, followed by the addition of bromine to the double bond, and finally adding 7- Oxygen-bicyclo[2.2.1]heptane-5,6-dibromoic anhydride, amine compounds, stirred at room temperature, monitored by TLC spot plate, after the reaction, filtered, washed with acetonitrile and dried in infrared target compound

Method used

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  • Method for green synthesis of norcantharidin derivative
  • Method for green synthesis of norcantharidin derivative
  • Method for green synthesis of norcantharidin derivative

Examples

Experimental program
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Effect test

Embodiment 1

[0021]

[0022] with 5 mL of CH 2 Cl 2 Add maleic anhydride (10 mmol, 1 g) and freshly distilled furan (20 mmol, 1.4 g) to a 25 mL round bottom flask, stir at room temperature for 24 h, filter, wash with ether, and spin dry. Afterwards, under the protection of nitrogen, the bromine CH 2 Cl 2 The solution was added dropwise to the round-bottomed flask within 1 h. After the dropwise addition, the reaction solution was stirred and reacted at room temperature for 3.5 h. Then filter and filter with CH 2 Cl 2 The solid was washed to obtain a white solid. After the filtrate was spin-dried, it was washed with ether to obtain 7-oxo-bicyclo[2.2.1]heptane-5,6-dibromoic anhydride. Finally, add 7-oxo-bicyclo[2.2.1]heptane-5,6-dibromoic anhydride (1 mmol) and amine compound (0.5 mmol) to the Schlenk containing 2 mL of acetone, and stir at room temperature 1 s, TLC spot plate monitoring, after the reaction, filtered, washed with acetonitrile and dried by infrared. Yield 89%.

[...

Embodiment 2

[0025]

[0026] with 5 mL of CH 2 Cl 2 Add maleic anhydride (10 mmol, 1 g) and freshly distilled furan (20 mmol, 1.4 g) to a 25 mL round bottom flask, stir at room temperature for 24 h, filter, wash with ether, and spin dry. Afterwards, under the protection of nitrogen, the bromine CH 2 Cl 2 The solution was added dropwise to the round-bottomed flask within 1 h. After the dropwise addition, the reaction solution was stirred and reacted at room temperature for 3.5 h. Then filter and filter with CH 2 Cl 2 The solid was washed to obtain a white solid. After the filtrate was spin-dried, it was washed with ether to obtain 7-oxo-bicyclo[2.2.1]heptane-5,6-dibromoic anhydride. Finally, add 7-oxo-bicyclo[2.2.1]heptane-5,6-dibromoic anhydride (1 mmol) and amine compound (0.5 mmol) to the Schlenk containing 2 mL of acetone, and stir at room temperature After 10 hours, TLC spot plate monitoring, after the reaction, filtered, washed with acetonitrile and dried by infrared. Yiel...

Embodiment 3

[0029]

[0030] with 5 mL of CH 2 Cl 2 Add maleic anhydride (10 mmol, 1 g) and freshly distilled furan (20 mmol, 1.4 g) to a 25 mL round bottom flask, stir at room temperature for 24 h, filter, wash with ether, and spin dry. Afterwards, under the protection of nitrogen, the bromine CH 2 Cl 2 The solution was added dropwise to the round-bottomed flask within 1 h. After the dropwise addition, the reaction solution was stirred and reacted at room temperature for 3.5 h. Then filter and filter with CH 2 Cl 2 The solid was washed to obtain a white solid. After the filtrate was spin-dried, it was washed with ether to obtain 7-oxo-bicyclo[2.2.1]heptane-5,6-dibromoic anhydride. Finally, add 7-oxo-bicyclo[2.2.1]heptane-5,6-dibromoic anhydride (1 mmol) and amine compound (0.5 mmol) to the Schlenk containing 2 mL of acetone, and stir at room temperature 1s, TLC plate monitoring, after the reaction, filtered, washed with acetonitrile and dried by infrared. Yield 84%.

[0031] ...

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Abstract

The invention relates to a method for green synthesis of a norcantharidin derivative and aims to solve problems of complexity of reaction steps and raw material types, long reaction time and low yield in existing norcantharidin derivative synthesis and high solvent toxicity in some methods. The method for green synthesis of the norcantharidin derivative includes: subjecting furan and maleic anhydride to Diels-Alder reaction at the room temperature to obtain norcantharidin; then performing addition of bromine pair double bonds; finally, adding 7-oxy-bicyclo[2.2.1]heptanes-5,6-dibromoanhydride and amine compounds into Schlenk filled with acetone, stirring at the room temperature, performing TLC (thin-layer chromatography) monitoring, and after reaction is finished, carrying out filtering, acetonitrile washing and infrared drying to obtain a target compound. The method has advantages of safety, environment friendliness, freeness of generation of waste gas and waste water, simplicity and convenience in operation, high in process stability and yield and realization of reaction at the room temperature.

Description

technical field [0001] The invention relates to the fields of organic chemistry and medicinal chemistry, in particular to a green synthesis method of norcantharidin derivatives. Background technique [0002] Norcantharidin derivatives are an important class of chemically synthesized drugs. Norcantharidin derivatives can show good anti-tumor, anti-virus, increase white blood cells and improve pancreatic function in medicine. It has the advantages of low toxicity and high anticancer efficiency. Research work on the synthesis of norcantharidin derivatives and the structural modification and derivatization of cantharidin molecules has attracted much attention. In addition, due to the complex process of synthesizing such compounds, many reaction steps, various raw materials, long reaction time, low yield, and the problem of high toxicity of solvents in some methods. In view of the above problems, it is very necessary to develop a synthetic route with single raw material, short...

Claims

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Application Information

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IPC IPC(8): C07D493/08
CPCC07D493/08
Inventor 黄超孙荣荣尹艳清杨丽娟袁明龙
Owner YUNNAN MINZU UNIV
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