Chiral spiro indole-pyran pyridine alkaline compound and preparation and application thereof
A technology for pyrimidine bases and compounds, applied in chiral spirocyclic indole-pyranyl pyrimidine base compounds and their preparation, and the application field of preparing broad-spectrum anticancer drugs, which can solve the problems of no cancer treatment plan
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Embodiment 1
[0038] Embodiment 1, ( R Preparation of )-spirocyclic indole-pyranyrimidine base-7a
[0039] 32.4 mg (0.2 mmol) of substrate 4 - Hydroxycoumarin compound 1b and 13.0 mg (0.02 mmol) of rosin-derived chiral thiourea catalyst were dissolved in 1.5 ml of dichloromethane; another reaction substrate 46.0 mg (0.22 mmol) of dicyanoindoxin was added at room temperature Oleene compound 1c, reacted at room temperature for 6 hours. After the reaction was complete, 73.4 mg of the product intermediate was obtained by column chromatography (H60 silica gel, ethyl acetate:dichloromethane=1:10) (yield: 99%). Then the product intermediate was dissolved in a mixed solution of 2.0 ml of anhydrous anhydride and 1.0 ml of pyridine, and reacted at 60° C. for 3 hours. After the reaction was complete, it was extracted with dichloromethane, dried over anhydrous sodium sulfate, and separated by column chromatography (H60 silica gel, ethyl acetate:dichloromethane=1:5) to obtain a white solid as the fin...
Embodiment 2
[0047] Example 2: ( R Preparation of )-spirocyclic indole-pyranyrimidine base-8a
[0048] 32.4 mg (0.2 mmol) of substrate 4 - Hydroxycoumarin compound 1b and 13.0 mg (0.02 mmol) of rosin-derived chiral thiourea catalyst were dissolved in 1.5 ml of dichloromethane; another reaction substrate 51.7 mg (0.22 mmol) of dicyanoindoxin was added at room temperature Oleene compound 2c was reacted at room temperature for 8 hours. After the reaction was complete, the product intermediate was separated by column chromatography (H60 silica gel, ethyl acetate:dichloromethane=1:10). Then the product intermediate was dissolved in a mixed solution of 2.0 ml of anhydrous anhydride and 1.0 ml of pyridine, and reacted at 60° C. for 3 hours. After the reaction was complete, it was extracted with dichloromethane, dried over anhydrous sodium sulfate, and column chromatography (H60 silica gel, ethyl acetate:dichloromethane=1:5) gave a white solid as the final product——( R )-spirocyclic indole-pyr...
Embodiment 3
[0056] Example 3: ( R Preparation of )-spirocyclic indole-pyranyrimidine base-8b
[0057] 32.4 mg (0.2 mmol) of substrate 4 - Hydroxycoumarin compound 1b and 13.0 mg (0.02 mmol) of rosin-derived chiral thiourea catalyst were dissolved in 1.5 ml of dichloromethane; another reaction substrate 58.3 mg (0.22 mmol) of dicyanoindoxin was added at room temperature Oleene compound 3c was reacted at room temperature for 8 hours. After the reaction was complete, the product intermediate was separated by column chromatography (H60 silica gel, ethyl acetate:dichloromethane=1:10). Then the product intermediate was dissolved in a mixed solution of 2.0 ml of anhydrous anhydride and 1.0 ml of pyridine, and reacted at 60° C. for 3 hours. After the reaction was complete, it was extracted with dichloromethane, dried over anhydrous sodium sulfate, and column chromatography (H60 silica gel, ethyl acetate:dichloromethane=1:5) gave a white solid as the final product——( R )-spiroindole-pyranopyri...
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