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Dehydroabietyl-3,4-dihydropyrimidine-2(1H)-one derivative as well as preparation method and application thereof

A technology of dihydropyrimidine and derivatives, applied in organic chemistry, antiviral agents, etc., can solve problems such as many side reactions, low yield, harsh reaction conditions, etc., and achieve enhanced reprocessing and utilization, high yield, and post-treatment. easy effect

Active Publication Date: 2018-12-21
INST OF CHEM IND OF FOREST PROD CHINESE ACAD OF FORESTRY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the synthesis of existing dihydropyrimidinone derivatives has the disadvantages of harsh reaction conditions, many side reactions, and low yield.

Method used

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  • Dehydroabietyl-3,4-dihydropyrimidine-2(1H)-one derivative as well as preparation method and application thereof
  • Dehydroabietyl-3,4-dihydropyrimidine-2(1H)-one derivative as well as preparation method and application thereof
  • Dehydroabietyl-3,4-dihydropyrimidine-2(1H)-one derivative as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0047] The preparation of compound a:

[0048]

[0049] Add 7mmol of dehydroabietic acid thiosemicarbazide, 7mmol of ethyl acetoacetate, 7mmol of benzaldehyde, 0.7mmol of ytterbium p-trifluoromethanesulfonate, and 20mL of ethanol in sequence in a 50mL eggplant-shaped bottle, heat up to 80°C, and install a reflux device. And react under stirring for 12h, then add 50mL water to the reaction solution to quench; the obtained reaction material is extracted three times with 50mL ethyl acetate, and then washed with water once, the organic phase is combined, the obtained organic phase is rotary evaporated, concentrated, and then Compound a was obtained through silica gel column separation; wherein, during silica gel column chromatography separation, the eluent used was a mixture of petroleum ether and ethyl acetate at a volume ratio of 4:1, and the particle size of the silica gel particles was 100-200 mesh.

[0050] Yield: 82%, yellow solid (96%); MS (ESI) m / z 572 [M-H]-. 1 HNMR(4...

Embodiment 2

[0052] Preparation of compound b:

[0053]

[0054] Add 7mmol of dehydroabietic acid thiosemicarbazide, 7mmol of ethyl acetoacetate, 7mmol of 3-methoxybenzaldehyde, 0.7mmol of ytterbium p-trifluoromethanesulfonate, and 20mL of ethanol in sequence in a 50mL eggplant-shaped bottle, and heat up to 80°C. Install the reflux device, and react under stirring for 12h, then add 50mL water to the reaction liquid to quench; the obtained reaction material is extracted three times with 50mL ethyl acetate, and then washed with water once, the organic phase is combined, and the obtained organic phase is vortexed Evaporation, concentration, and then separated by silica gel column to obtain compound b; wherein, during silica gel column chromatography separation, the eluent used is a mixture of petroleum ether and ethyl acetate with a volume ratio of 4:1, and the particle size of the silica gel particle is 100 -200 mesh.

[0055] Yield: 83%, yellow solid (96%); MS (ESI) m / z 602 [M-H]-. 1 HNM...

Embodiment 3

[0057] Preparation of compound c:

[0058]

[0059] Add 7mmol of dehydroabietic acid thiosemicarbazide, 7mmol of ethyl acetoacetate, 7mmol of 4-bromobenzaldehyde, 0.7mmol of ytterbium p-trifluoromethanesulfonate, and 20mL of ethanol in sequence in a 50mL eggplant-shaped bottle. Reflux device, and react under stirring for 12h, then add 50mL water to the reaction solution to quench; the obtained reaction material is extracted three times with 50mL ethyl acetate, then washed with water once, the organic phase is combined, and the obtained organic phase is subjected to rotary evaporation, Concentrated, and then separated by silica gel column to obtain compound c; wherein, during silica gel column chromatography separation, the eluent used is a mixture of petroleum ether and ethyl acetate with a volume ratio of 4:1, and the particle size of the silica gel particles is 100-200 head.

[0060] Yield: 83%, yellow solid (97%); MS (ESI) m / z 650 [M-H] – . 1 HNMR(400MHz,DMSO)δ10.03–9...

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Abstract

The invention discloses a dehydroabietyl-3,4-dihydropyrimidine-2(1H)-one derivative as well as a preparation method and the application thereof. The molecular structural formula of the dehydroabietyl-3,4-dihydropyrimidine-2(1H)-one derivative is shown in the description, wherein R is phenyl, 3-methoxyphenyl, 4-bromopheny, 4-trifluoromethylphenyl, 4-fluorophenyl, 3,4-difluorophenyl, 4-chlorphenyl or 2,6-dichlorophenyl. The dehydroabietyl-3,4-dihydropyrimidine-2(1H)-one derivative disclosed by the invention has a good antiviral effect and a good inhibitory effect on influenza a virus and the like; the preparation method disclosed by the invention has the advantages of simple process, mild conditions, few side effects, high yield, high purity, simple post-treatment, high activity of the obtained product, low cost of reaction raw materials and the like; the reprocessing and utilization of rosin are enhanced, the use value of the rosin is improved and the use of petrochemical resources is reduced.

Description

technical field [0001] The invention relates to a dehydroabietyl-3,4-dihydropyrimidin-2(1H)-one derivative, a preparation method and application thereof, belonging to the field of organic synthesis. Background technique [0002] With the decrease of petroleum resources, the research and development of renewable resources instead of petroleum products to produce various materials has become a global research hotspot. Rosin is an important forest product in my country, with an annual output of more than 800,000 tons. Therefore, strengthening the reprocessing of rosin and improving the use value and application range of rosin is an urgent problem to be solved. [0003] Dihydropyrimidinones have important pharmacological activities, such as calcium antagonists, antihypertensive agents and antagonists, and are widely used in antibacterial, antiviral, antitumor, anti-inflammatory and other fields. However, the existing synthesis of dihydropyrimidinone derivatives has the disadva...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D239/22A61P31/16A61P31/12
CPCA61P31/12A61P31/16C07D239/22
Inventor 沈明贵罗云龙商士斌王丹宋杰
Owner INST OF CHEM IND OF FOREST PROD CHINESE ACAD OF FORESTRY
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