A method for synthesizing side chain functionalized 4-acylpyrazoles by cyclic ketone hydrazone
A technology of acylpyrazoles and functional grouping, applied in organic chemistry, etc., can solve the problems of expensive raw materials, limited synthetic methods, and long synthetic routes, and achieve low raw material prices, avoid resource waste and environmental pollution, and high synthesis efficiency Effect
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Embodiment 1
[0015]
[0016] Add 1a (0.6mmol, 80mg), copper acetate (Cu(OAc) 2 , 0.1mmol, 18mg), 2,2'-bipyridine (bpy, 0.1mmol, 16mg), 2,2,6,6-tetramethylpiperidine nitrogen oxide (TEMPO, 0.5mmol, 78mg) and chlorobenzene (PhCl, 3mL), the reaction tube was sealed after being evacuated and filled with nitrogen, and placed in an oil bath at 120°C to stir for 10 h. Then 2a (0.5 mmol, 87 mg) was added to the reaction system, and the stirring reaction was continued in an oil bath at 120° C. for 4 h in an air atmosphere. The reaction was quenched by adding 10 mL of water, extracted with ethyl acetate (10 mL×3), and then the organic phase was washed with water and saturated brine in sequence, and dried over anhydrous sodium sulfate. It was filtered, spin-dried, and separated on a silica gel column (petroleum ether / ethyl acetate=10 / 1) to obtain 3a (78 mg, 36%) as a colorless oily liquid. The characterization data of this compound are as follows: 1 H NMR (400MHz, CDCl 3 )δ: 1.42-1.52(m, 4H), ...
Embodiment 2
[0018] Add 1a (1.2mmol, 161mg), Cu(OAc) 2 (0.1mmol, 18mg), bpy (0.1mmol, 16mg), TEMPO (0.5mmol, 78mg) and chlorobenzene (3mL), vacuumize and fill the reaction tube with nitrogen gas, seal the reaction tube, and place it in an oil bath at 120°C for 10h with stirring . Then 2a (0.5 mmol, 87 mg) was added to the reaction system, and the stirring reaction was continued in an oil bath at 120° C. for 4 h in an air atmosphere. The reaction was quenched by adding 10 mL of water, extracted with ethyl acetate (10 mL×3), and then the organic phase was washed with water and saturated brine in sequence, and dried over anhydrous sodium sulfate. It was filtered, spin-dried, and separated on a silica gel column (petroleum ether / ethyl acetate=10 / 1) to obtain 3a (91 mg, 42%) as a colorless oily liquid.
Embodiment 3
[0020] Add 1a (1.2mmol, 161mg), Cu(OAc) 2 (0.2mmol, 36mg), bpy (0.1mmol, 16mg), TEMPO (0.5mmol, 78mg) and chlorobenzene (3mL), vacuumize and fill the reaction tube with nitrogen gas, seal the reaction tube, and place it in an oil bath at 120°C for 10h with stirring . Then 2a (0.5 mmol, 87 mg) was added to the reaction system, and the stirring reaction was continued in an oil bath at 120° C. for 4 h in an air atmosphere. The reaction was quenched by adding 10 mL of water, extracted with ethyl acetate (10 mL×3), and then the organic phase was washed with water and saturated brine in sequence, and dried over anhydrous sodium sulfate. It was filtered, spin-dried, and separated on a silica gel column (petroleum ether / ethyl acetate=10 / 1) to obtain 3a (109 mg, 55%) as a colorless oily liquid.
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