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Method for catalytically synthesizing xanthenedione compound open ring derivatives through hydroxyl ammonium ionic liquid

A technology of xanthene dione and ionic liquid is applied in the field of green synthesis of fine chemicals, and achieves the effects of simple preparation, non-corrosive equipment and reduced energy consumption

Inactive Publication Date: 2016-12-14
HENAN NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The acidity and alkalinity of alcoholamine ionic liquids can be regulated by the length of substituent on its cation and the acidity and alkalinity of anion, and can effectively promote Friedel-Crafts reaction (Sanap.A K, Shankarling.G S.RSC Advances, 2014, 4, 34938), Henry reaction (Sing.B S, Lobo.H R, Shankarling.G S. Catalysis Communications, 2012, 24, 70), Knoevenagel reaction (Zhu A L, Liu R X, Li L J, et al.Catalysis Today ,2013,200,17) and Biginelli reaction (ZhuA L, Liu Q Q, Li L J, et al.Catalysis letters, 2013,143,463), but there are no articles or related patents reporting its catalytic synthesis of xanthene diketone Application of ring-opened derivatives of compound-like compounds

Method used

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  • Method for catalytically synthesizing xanthenedione compound open ring derivatives through hydroxyl ammonium ionic liquid
  • Method for catalytically synthesizing xanthenedione compound open ring derivatives through hydroxyl ammonium ionic liquid

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0013] In the round bottom flask, first add the alcohol amine ionic liquid DMEAAc (0.5mmol), then add p-nitrobenzaldehyde (0.5mmol), stir and mix evenly, and then add 5,5-dimethyl-1,3-cyclo Hexanedione (1 mmol), then stirred at room temperature for 1.5 h, and the entire reaction process was detected by TLC until the reaction was completed. Finally, the crude product is washed with a mixed solution of water and ethanol, and then dried to obtain a pure product with a yield of 94%.

Embodiment 2

[0015] Add alcohol amine ionic liquid DMEAPr (0.1mmol) first to the round bottom flask, then add o-nitrobenzaldehyde (0.5mmol), stir and mix evenly, and then add 5,5-dimethyl-1,3-cyclo Hexanedione (1 mmol), then stirred at room temperature for 3 h, and the entire reaction process was detected by TLC until the reaction was completed. Finally, the crude product is washed with a mixed solution of water and ethanol, and then dried to obtain a pure product with a yield of 90%.

Embodiment 3

[0017] In the round bottom flask, first add the alcohol amine ionic liquid DMEAPr (0.05mmol), then add m-nitrobenzaldehyde (0.5mmol), stir and mix evenly, and then add 5,5-dimethyl-1,3-cyclo Hexanedione (1 mmol), then stirred at room temperature for 2 h, and the entire reaction process was detected by TLC until the end of the reaction. Finally, the crude product is washed with a mixed solution of water and ethanol, and then dried to obtain a pure product with a yield of 89%.

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Abstract

The invention discloses a method for catalytically synthesizing xanthenedione compound open ring derivatives through hydroxyl ammonium ionic liquid, and belongs to the technical field of green synthesis of fine chemicals. According to the technical scheme, the method is characterized in that aldehyde compounds and dimedone serve as the substrates, the hydroxyl ammonium ionic liquid serves as the catalyst, stirring reaction is conducted for 0.5-4 h at room temperature, and then the target products, namely the xanthenedione compound open ring derivatives, are prepared. The method is implemented under the condition of no solvent, volatile organic solvent is effectively prevented from being used, the cost of the reaction process is reduced, and the harms to operators are reduced; the reaction is conducted at room temperature, no heating is needed, and energy consumption and requirements for devices are lowered; by means of the catalysis system, the gram-scale preparation can be conveniently achieved.

Description

technical field [0001] The invention belongs to the technical field of green synthesis of fine chemicals, and specifically relates to a method for synthesizing ring-opening derivatives of xanthene diketones by catalysis of alcohol amine ionic liquids. Background technique [0002] The ring-opened derivatives of xanthene diones are the structural units of many natural product molecules, occupy an important position in medicinal chemistry, and have important pharmacological and physiological activities, such as antiviral substances and antibacterial drugs. In addition, they have many uses in dyes, fluorescent materials and laser technology. The traditional method of synthesizing ring-opening derivatives of xanthenediones is mostly the reaction between active methylene compounds and aromatic aldehydes under the action of acidic catalysts. These Bronsted acid or Lewis acidic catalysts include dodecylbenzenesulfonate Acid (T.S.Jin, J.S.Zhang, T.T.Guo, et al. Synlett., 2004, 866)...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C201/12C07C205/45C07C45/74C07C49/747C07C49/753C07C221/00C07C225/22C07D213/50C07D307/46
CPCC07C45/74C07C201/12C07C221/00C07D213/50C07D307/46C07C205/45C07C49/747C07C49/753C07C225/22
Inventor 朱安莲李凌君李志勇杜春燕王明月
Owner HENAN NORMAL UNIV
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