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1, 3, 5-triazine-2-ketospirooxindole compound and preparation method

A technology for spirocyclic indolinone and compound is applied in the field of compound preparation and achieves the effects of simple operation, easy preparation and low cost

Inactive Publication Date: 2019-09-20
BEIJING UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

So far, there are few literature reports on the cycloaddition reaction of N,N'-dialkoxy substituted urea, which has a lot of room for development

Method used

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  • 1, 3, 5-triazine-2-ketospirooxindole compound and preparation method
  • 1, 3, 5-triazine-2-ketospirooxindole compound and preparation method
  • 1, 3, 5-triazine-2-ketospirooxindole compound and preparation method

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0030]

[0031] Weigh N, N'-dialkoxy substituted urea 1a (27.2 mg, 0.1 mmol) and trifluoroethyl substituted isatin-3-imine 2a (48.4 mg, 0.2 mmol) and dissolve in DME (0.5 mL ), which was slowly added to a solution of NaH (12.0 mg, 0.3 mmol, 60% dispersed in kerosene) in TFP (0.5 mL) at 0°C. Then weigh the oxidant PhI(OH)(OTs) (78.4mg, 0.2mmol), dissolve it in DME (1.5mL), and slowly add it dropwise to the reaction system within one minute, and react at 0°C to room temperature. The mixed solution was stirred well (the reaction was checked by TLC) until the trifluoroethyl-substituted isatin-3-imine 2a was completely consumed. Finally, the reaction mixture solution was concentrated under reduced pressure, and the crude product was subjected to column chromatography (the eluent was selected as a mixed solution of petroleum ether / ethyl acetate with a volume ratio of 5:1) to obtain the target product trans-3aa (33.3 mg), The yield was 65%.

[0032] Characterization and analysis...

Embodiment 2

[0034]

[0035]Weigh N, N'-dialkoxy substituted urea 1a (27.2 mg, 0.1 mmol) and trifluoroethyl substituted isatin-3-imine 2b (64.0 mg, 0.2 mmol) and dissolve in DME (0.5 mL ) was slowly added to a solution of NaH (12.0 mg, 0.3 mmol, 60% dispersed in kerosene) in TFP (0.5 mL) at 0°C. Then weigh the oxidant PhI(OH)(OTs) (78.4mg, 0.2mmol), dissolve it in DME (1.5mL), and slowly add it dropwise to the reaction system within one minute, and react at 0°C to room temperature. The mixed solution was stirred well (the reaction was monitored by TLC) until the trifluoroethyl-substituted isatin-3-imine 2b was completely consumed. Finally, the reaction mixture solution was concentrated under reduced pressure, and the crude product was subjected to column chromatography (the eluent was selected as a mixed solution of petroleum ether / ethyl acetate with a volume ratio of 5:1) to obtain the target product trans-3ab (47.2 mg), The yield was 80%.

[0036] Characterization and analysis of th...

Embodiment 3

[0038]

[0039] Weigh N,N'-dialkoxy substituted urea 1a (27.2 mg, 0.1 mmol) and trifluoroethyl substituted isatin-3-imine 2c (55.2 mg, 0.2 mmol) and dissolve in DME (0.5 mL ) was slowly added to a solution of NaH (12.0 mg, 0.3 mmol, 60% dispersed in kerosene) in TFP (0.5 mL) at 0°C. Then weigh the oxidant PhI(OH)(OTs) (78.4mg, 0.2mmol), dissolve it in DME (1.5mL), and slowly add it dropwise to the reaction system within one minute, and react at 0°C to room temperature. The mixed solution was stirred well (the reaction was checked by TLC) until the trifluoroethyl-substituted isatin-3-imine 2c was completely consumed. Finally, the reaction mixture solution was concentrated under reduced pressure, and the crude product was subjected to column chromatography (the eluent was selected as a mixed solution of petroleum ether / ethyl acetate with a volume ratio of 5:1) to obtain the target product trans-3ac (37.1 mg), The yield was 68%.

[0040] Characterization and analysis of the ...

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Abstract

Belonging to the technical field of compound preparation, the invention relates to a 1, 3, 5-triazine-2-ketospirooxindole compound and a preparation method. The specific experimental method includes: weighing N, N'-dialkoxy substituted urea and trifluoroethyl substituted isatin-3-imide, dissolving the substances in DME, then adding the mixture into an NaH dissolved TFP solution at 0DEG C; then weighing an oxidant and performing dissolving in DME, then adding the obtained mixture dropwise into a reaction system, and fully stirring the reaction mixed solution (by TLC detection reaction) under a 0DEG C to room temperature condition till complete consumption of the trifluoroethyl substituted isatin-3-imide; and performing pressure reduced concentration, and subjecting a crude product to column chromatography, thus obtaining the 1, 3, 5-triazine-2-ketospirooxindole compound. The synthesis method can achieve excellent diastereomer selectivity and a chemical yield of medium level or above, and is a brand new method for efficient and concise synthesis of the 1, 3, 5-triazine-2-ketospirooxindole compound with potential bioactivity.

Description

technical field [0001] The invention specifically relates to a preparation method of a novel 1,3,5-triazin-2-one spiro indolone compound, which belongs to the technical field of compound preparation. Background technique [0002] Spiral indolones have unique spatial and chemical structures, and have a wide range of biological activities, such as anti-tumor, treatment of diabetes, anti-bacterial, anti-tuberculosis, etc., and have important application value in the field of medicinal chemistry research. At present, the methods and strategies for the synthesis and construction of spiro indolinones with structural diversity and complexity still have a lot of room for development. Therefore, the design and development of new, efficient, environmentally friendly, mild reaction conditions, and easy-to-operate organic synthesis methods, and the stereoselective construction of spiro indolinones with various spiroheterocyclic skeleton structures, not only greatly enriched the spiro-in...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D487/10
CPCC07B2200/07C07D487/10
Inventor 赵洪武郭家明王立茹丁晚秋汤喆吴慧慧范晓祖毕晓帆
Owner BEIJING UNIV OF TECH
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