Synthetic method and application of a copper-catalyzed one-pot method for preparing c-4 sulfone group-substituted isoquinolinone compounds
A technology of isoquinolinone and synthesis method, which is applied in the direction of organic chemistry, can solve problems such as limited methods, and achieve the effect of less reaction steps, high yield and good functional group compatibility
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Embodiment 1
[0039]
[0040] At room temperature, add the corresponding 2-bromo-N-phenylbenzenesulfonamide compound (0.2mmol), benzenesulfonyl acetonitrile ( 0.3 mmol), cuprous chloride (0.4mmol), N,N'-dimethylethylenediamine (0.04mmol), sodium carbonate (0.4 mmol), add 2.0mL DMSO with a syringe under nitrogen, put the reaction tube Stir in an oil bath at 110°C for 24 hours. The resulting solution was cooled to room temperature, 2 mL of deionized water was added to the reaction liquid, and mixed evenly, each time 3 mL of ethyl acetate was used as the extractant to extract the crude product from the reaction liquid through liquid separation and extraction, and the extracts were combined. And the solvent was removed by a rotary evaporator; the residue was purified with a silica gel column (the specification of silica gel was 200 mesh to 300 mesh, and the eluent was petroleum ether / ethyl acetate (3:1v / v)) to obtain 48.9 mg of the target product, Yield 65%.
[0041] 1 H NMR (DMSO-d 6 ,5...
Embodiment 2
[0045]
[0046] At room temperature, add the corresponding 2-bromo-N-phenylbenzenesulfonamides (0.2mmol), 4-methylbenzene to a 25 ml Schlenk (Schlenk) tube filled with nitrogen and equipped with a magnetic stirrer Sulfonyl acetonitrile (0.2 mmol), cuprous chloride (0.02 mmol), N,N'-dimethylethylenediamine (0.04 mmol), sodium carbonate (0.6 mmol), 2.0 mL DMF was added by syringe under nitrogen, The reaction tube was placed in an oil bath at 110°C and stirred for 24 hours. The resulting solution was cooled to room temperature, 2 mL of deionized water was added to the reaction liquid, and mixed evenly, each time 3 mL of ethyl acetate was used as the extractant to extract the crude product from the reaction liquid through liquid separation and extraction, and the extracts were combined. And the solvent was removed by a rotary evaporator; the residue was purified with a silica gel column (the specification of silica gel was 200 mesh to 300 mesh, and the eluent was petroleum ethe...
Embodiment 3
[0051]
[0052] At room temperature, add the corresponding 2-bromo-N-phenylbenzenesulfonamides (0.2mmol), 4-chlorobenzenesulfonamides to a 25 ml Schlenk (Schlenk) tube filled with nitrogen and equipped with a magnetic stir bar. Acylacetonitrile (0.4 mmol), cuprous bromide (0.05 mmol), N,N'-dimethylethylenediamine (0.06 mmol), potassium carbonate (0.7 mmol) were added with 2.0 mL NMP by syringe under nitrogen, and the reaction The tube was placed in an oil bath at 110°C and stirred for 12 hours. The resulting solution was cooled to room temperature, 2 mL of deionized water was added to the reaction liquid, and mixed evenly, each time 3 mL of ethyl acetate was used as the extractant to extract the crude product from the reaction liquid through liquid separation and extraction, and the extracts were combined. And the solvent was removed by a rotary evaporator; the residue was purified with a silica gel column (the specification of silica gel was 200 mesh to 300 mesh, and the e...
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