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Synthesis method of 2H-1-benzopyran-2-ketone derivatives

A technology of benzopyran and synthesis method, which is applied in the field of synthesis of 2H-1-benzopyran-2-one derivatives, can solve the problems of cumbersome operation, severe reaction conditions, large amount of catalyst, etc., and achieve chemical selection High stability, high product yield and low production cost

Inactive Publication Date: 2013-01-23
SOUTHWEST UNIV
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  • Claims
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Problems solved by technology

[0003] The traditional synthesis method of 2H-1-benzopyran-2-one and its derivatives uses Lewis acid or inorganic acid as a catalyst, which has many disadvantages such as multi-step reaction, cumbersome operation, severe reaction conditions, and large amount of catalyst.
However, most of the enzyme-catalyzed reactions reported in the literature are single-step reactions, and there are fewer reports on multi-step reactions catalyzed by a single enzyme. The synthesis of 2H-1-benzopyran-2-one derivatives Not yet reported

Method used

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  • Synthesis method of 2H-1-benzopyran-2-ketone derivatives
  • Synthesis method of 2H-1-benzopyran-2-ketone derivatives
  • Synthesis method of 2H-1-benzopyran-2-ketone derivatives

Examples

Experimental program
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Effect test

Embodiment 1～35

[0017] Examples 1-35. Synthesis of 3-acetyl-2H-1-benzopyran-2-one by enzyme-catalyzed dominoic / intramolecular transesterification of salicylaldehyde and ethyl acetoacetate

[0018]

[0019] Add salicylaldehyde, ethyl acetoacetate, organic solvent, water and enzyme in the round bottom flask, constant temperature stirring reaction, after the completion of the reaction, filter, the filter cake is washed with dichloromethane, the combined filtrate and lotion, add water (20ml ) after dilution, extracted 3 times (each 20ml) with dichloromethane, combined the dichloromethane extracts, dried with anhydrous sodium sulfate, then removed the solvent by distillation under reduced pressure to obtain the crude product, and the crude product was purified by flash column chromatography , the target product is obtained. The reaction conditions and results are shown in Table 1.

[0020] Table 1, Synthesis conditions and results of 3-acetyl-2H-1-benzopyran-2-one

[0021]

[0022]

[0...

Embodiment 36～49

[0024] Examples 36-49, Synthesis of 2H-1-benzopyran-2-one derivatives by alkaline protease-catalyzed salicylaldehyde or its derivatives and β-keto ester dominoic culture / intramolecular transesterification reaction

[0025]

[0026] Add salicylaldehyde or its derivatives (1.64mmol), β-ketoester (4.9mmol), DMSO (4.5mL), water (0.5mL) and alkaline protease (100mg) in a round bottom flask, temperature 55°C Stir the reaction, after the reaction is complete, filter, the filter cake is washed with dichloromethane, combine the filtrate and washings, add water (20ml) to dilute, extract 3 times with dichloromethane (each 20ml), and combine the dichloromethane extracts , dried with anhydrous sodium sulfate, and then distilled off the solvent under reduced pressure to obtain a crude product, which was purified by flash column chromatography to obtain 2H-1-benzopyran-2-one derivatives. The reaction conditions and results are shown in Table 2.

[0027] Table 2, Synthetic conditions and ...

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Abstract

The invention relates to the field of chemistry, in particular to a synthesis method of 2H-1-benzopyran-2-ketone derivatives. The method comprises the step of carrying out Knoevenagel reaction and intramolecular ester exchang reaction to salicylaldehyde with a general formula II and derivatives thereof and beta-keto ester with a general formula III in a solvent in the presence of the catalysis ofalkali protease to prepare the 2H-1-benzopyran-2-ketone derivatives with a general formula I. The method has the advantages of simple and convenient operation, mild reaction condition, high chemical selectivity, high product yield, low cost and easy obtainment of enzyme, low production cost, easy realization of industrial production and the like.

Description

technical field [0001] The present invention relates to a compound synthesis method, in particular to a synthesis method of 2H-1-benzopyran-2-one derivatives. Background technique [0002] 2H-1-benzopyran-2-one and its derivatives have good biological activities such as anti-inflammatory, analgesic, antibacterial, antiviral, anticoagulant, antioxidative, antiproliferative, anticancer, and regulation of the central nervous system etc., are widely used in food, medicine, cosmetics, agricultural chemicals, spices, dyes and other fields; in addition, it can also be used as an intermediate for the synthesis of compounds such as benzopyrans and coumarones. Therefore, the research on the synthesis of 2H-1-benzopyran-2-one and its derivatives has attracted great attention of organic chemists and medicinal chemists. [0003] The traditional synthesis method of 2H-1-benzopyran-2-one and its derivatives uses Lewis acid or inorganic acid as a catalyst, which has many disadvantages such...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C12P17/06
Inventor 何延红官智王昌恒
Owner SOUTHWEST UNIV
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