Ionic liquid-promoted one-pot method for synthesizing 4H-pyranocoumarin derivatives

A technology of coumarin derivatives and ionic liquids, applied in chemical instruments and methods, organic compound/hydride/coordination complex catalysts, chemical/physical processes, etc., to achieve convenient recycling, high atom economy, and easy operation and the effect of simple post-processing

A technology of coumarin derivatives and ionic liquids, applied in chemical instruments and methods, organic compound/hydride/coordination complex catalysts, chemical/physical processes, etc., to achieve convenient recycling, high atom economy, and easy operation and the effect of simple post-processing

CN110156809AInactive Publication Date: 2019-08-23HENAN NORMAL UNIV
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  • Ionic liquid-promoted one-pot method for synthesizing 4H-pyranocoumarin derivatives
  • Ionic liquid-promoted one-pot method for synthesizing 4H-pyranocoumarin derivatives
  • Ionic liquid-promoted one-pot method for synthesizing 4H-pyranocoumarin derivatives

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0022] Add 0.5mmol functionalized ionic liquid [TEOA][Ac], 0.5mmol 4-hydroxycoumarin, 0.5mmol benzaldehyde and 0.5mmol malononitrile in a round bottom flask, stir and mix with magnetic force, and stir at room temperature Reaction for 1.5h. TLC is used to track and monitor the whole process. After the reaction is over, add water twice for washing and centrifugation. After several times, wash with n-hexane to obtain pure product. Then it was placed in an oven and dried at 50°C, and the yield was 71%.

Embodiment 2

[0024] Add 0.5mmol functionalized ionic liquid [TEOA][Ac], 0.5mmol 4-hydroxycoumarin, 0.5mmol 4-nitrobenzaldehyde and 0.5mmol malononitrile into the round-bottom flask. The reaction was stirred at room temperature for 0.5h, and the whole process was monitored by TLC. After the reaction is over, add water twice for washing and centrifugation. After several times, wash with n-hexane to obtain pure product. Then it was placed in an oven and dried at 50°C, and the yield was 95%.

Embodiment 3

[0026] Add 0.5mmol functionalized ionic liquid [TEOA][Ac], 0.5mmol 4-hydroxycoumarin, 0.5mmol 3-nitrobenzaldehyde and 0.5mmol malononitrile into the round-bottom flask successively. The reaction was stirred at room temperature for 50 min. TLC is used to track and monitor the whole process. After the reaction is over, add water twice for washing and centrifugation. After several times, wash with n-hexane to obtain pure product. Then it was placed in an oven and dried at 50°C. The yield was 91%.

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Abstract

The invention discloses ionic liquid-promoted one-pot method for synthesizing 4H-pyranocoumarin derivatives. The method comprises the steps of performing a reaction under stirring for 0.5-12 h by using 4-hydroxycoumarin, one aromatic aldehyde compound and malononitrile as reaction substrates and a functionalized ionic liquid as a catalyst at room temperature to obtain one target product 4H-pyranocoumarin derivative. According to the method provided by the invention, the ionic liquid catalyst used in the method is simple and convenient to prepare, and the raw materials have good biocompatibility, and are cheap and easy to obtain; the one-pot method for preparing the 4H-pyranocoumarin derivatives has mild reaction conditions, does not need to add auxiliary agents such as a solvent, and has high atomic economy; the reaction system is non-corrosive to equipment, and has no special requirements for a reactor; the operation and post-treatment process of the catalytic system are simple, and the ionic liquid catalyst can be conveniently recycled; therefore, the method is a preferred method for industrial synthesis of the 4H-pyranocoumarin derivatives.

Description

Technical field [0001] The invention belongs to the technical field of synthesis of fine chemicals 4H-pyranocoumarin derivatives, and specifically relates to a one-pot synthesis method of 4H-pyranocoumarin derivatives promoted by ionic liquids. Background technique [0002] 4H-pyranocoumarin derivatives are an important class of heterocyclic compounds with a series of biological activities, such as anticonvulsants, diuretics, anticoagulants, etc., as well as anticancer and antimalarial activities. . Therefore, such compounds have received extensive attention in pharmacology and organic synthesis. At present, people have reported many methods for the synthesis of such derivatives. Potassium phthalimide (PPI) is useful in the reaction (H. Kiyani, F. Ghorbani, Res. Chem. Intermed. 41, 4031 (2015). )), N,N-Dimethylbenzylamine (DMBA) (H.Kiyani, MSJalali, Comb.Chem.High Throughput Screen.19,275(2016)), Cetyltrimethylammonium Bromide (CTAB) (AAJafari,M.Ghadami,Environ.Chem.Lett.14,21...

Claims

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Application Information

Patent Timeline
23 Aug 2019
Publication
CN110156809A
IPC
C07D493/04; B01J31/02; B01J31/04
CPC
B01J31/0285; B01J31/0298; B01J31/04; C07D493/04; Y02P20/584
Inventors
朱安莲; 冯婉鹿