Preparation method of spiroindoline compound
A technology for indoline spiro and ring compounds, which is applied in the field of rapid preparation of indoline spiro compounds, achieving the effects of short synthesis route, high atom utilization rate and simple operation process
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Embodiment 1
[0044] where R 1 is aryl, R 2 is aryl, R 3 is an alkyl group, namely (±)-1-benzyl-3,6-diphenyl-1 H -imidazo[1',2':1,2]pyrrolo[3,2- b ]indole-2,5(3 H , 7 H )-diketone synthesis, the specific steps are as follows:
[0045] In a microwave reaction tube of 10 ml size, the 3-amino-1 H - Indole-1-carboxylate tert-butyl ester (1.0 mmol) and benzaldehyde (1.0 mmol) were dissolved in 2.0 mL of methanol solution, followed by benzoylformic acid (1.0 mmol) and benzylisocyanate (1.0 mmol) was added to the solution one by one, the reaction solution was stirred overnight at room temperature, and then the isocyanate was detected by thin-layer chromatography. If there was no remaining isocyanine raw material, the solution was dried with nitrogen, and then dissolved in 10% TFA / DCE (5 mL). In the microwave 100 o After reacting with C for 10 minutes, the reaction mixture was diluted with ethyl acetate (15 ml), washed with saturated sodium carbonate solution and sodium chloride solution ...
Embodiment 2
[0048] where R 1 is aryl, R 2 is aryl, R 3 is an alkyl group, namely (±)-1-benzyl-3-(3,4-dichlorophenyl)-6-phenyl-1 H -imidazo[1',2':1,2]pyrrolo[3,2- b ] indole-2,5 (3 H , 7 H )-diketone synthesis, the specific steps are as follows:
[0049] In a microwave reaction tube of 10 ml size, the 3-amino-1 H -Indole-1-carboxylate tert-butyl ester (1.0 mmol) and 3,4-dichlorobenzaldehyde (1.0 mmol) were dissolved in 2.0 mL of methanol solution, and then benzoylformic acid (1.0 mmol ) and benzyl isocyanide (1.0 mmol) were sequentially added to the solution, the reaction solution was stirred overnight at room temperature, and then the isocyanate was detected by thin-layer chromatography. If there was no remaining isocyanine raw material, the solution was dried with nitrogen, and Redissolve in 10% TFA / DCE (5 mL). In the microwave 100 o After reacting with C for 10 minutes, the reaction mixture was diluted with ethyl acetate (15 ml), washed with saturated sodium carbonate solution ...
Embodiment 3
[0052] where R 1 is aryl, R 2 is aryl, R 3 is an alkyl group, namely (±)-1-benzyl-3-(4-methoxyphenyl)-6-phenyl-1 H -imidazo[1',2':1,2]pyrrolo[3,2- b ]indole-2,5(3 H , 7 H )-diketone synthesis, the specific steps are as follows:
[0053] In a microwave reaction tube of 10 ml size, the 3-amino-1 H -Indole-1-carboxylate tert-butyl ester (1.0 mmol) and 4-methoxybenzaldehyde (1.0 mmol) were dissolved in 2.0 mL of methanol solution, followed by benzoylformic acid (1.0 mmol) and benzyl isocyanide (1.0 mmol) were sequentially added to the solution, the reaction solution was stirred overnight at room temperature, and then the isocyanate was detected by thin-layer chromatography. If there was no remaining isocyanine raw material, the solution was dried with nitrogen, and then Dissolve in 10% TFA / DCE (5 mL). In the microwave 100 o After reacting with C for 10 minutes, the reaction mixture was diluted with ethyl acetate (15 ml), washed with saturated sodium carbonate solution and...
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