A kind of method that nbs promotes the polarity inversion of enaminone to synthesize diaminoalkene
A diaminoalkene and polarity reversal technology, applied in the direction of organic chemistry, can solve the problems of less research on enaminone functionalization reaction, narrow application range of substrates, high reaction cost, etc., to achieve wide application range of substrates, raw materials Inexpensive, easy post-processing effects
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Embodiment 1
[0056] Preparation of (E)-3-amino-2-(1H-benzo[d][1,2,3]triazol-1-yl)-3-phenylacrylate methyl ester:
[0057]
[0058] Mix NBS (N-bromosuccinimide, 213.58 mg, 1.2 mmol) and enamine I-a (177.08 mg, 1 mmol) in DMF (N,N'-dimethylformamide, 2 mL) at room temperature Stir. Ten minutes later, benzotriazole II-a (142.85 mg, 1.2 mmol) and solid Na 2 CO 3 (148.8 mg, 1.2 mmol). The mixture was then stirred at 80° C. for 2 hours under an air atmosphere. After cooling to room temperature, the reaction mixture was washed with 10 mL of saturated Na 2 S 2 o 3 It was washed with aqueous solution, and then extracted three times with ethyl acetate, each time using 10 mL of ethyl acetate. The combined organic layer was extracted three times with ethyl acetate and washed twice with brine, each time the amount of brine was 10 mL, and then washed with Na 2 SO 4 dry. The solvent was removed under reduced pressure, and the residue was purified by flash column chromatography on silica gel ...
Embodiment 2
[0060] (E)-3-Amino-2-(1H-benzo[d][1,2,3]triazol-1-yl)-3-(3,4-dimethoxyphenyl)methyl acrylate Preparation of:
[0061]
[0062] NBS (213.58 mg, 1.2 mmol) and enamine I-b (237.10 mg, 1 mmol) were mixed in DMF (2 mL) and stirred at room temperature. Ten minutes later, benzotriazole II-a (142.85 mg, 1.2 mmol) and solid Na 2 CO 3 (148.8 mg, 1.2 mmol). The mixture was then stirred at 80° C. for 2 hours under an air atmosphere. After cooling to room temperature, the reaction mixture was washed with 10 mL of saturated Na 2 S 2 o 3 It was washed with aqueous solution, and then extracted three times with ethyl acetate, each time using 10 mL of ethyl acetate. The combined organic layer was extracted three times with ethyl acetate and washed twice with brine, each time the amount of brine was 10 mL, and then washed with Na 2 SO 4 dry. The solvent was removed under reduced pressure, and the residue was purified by flash column chromatography on silica gel to give the desired p...
Embodiment 3
[0064] Preparation of (E)-3-amino-2-(1H-benzo[d][1,2,3]triazol-1-yl)-3-(p-tolyl)methyl acrylate:
[0065]
[0066] NBS (213.58 mg, 1.2 mmol) and enamine I-c (191.09 mg, 1 mmol) were mixed in DMF (2 mL) and stirred at room temperature. Ten minutes later, benzotriazole II-a (142.85 mg, 1.2 mmol) and solid Na 2 CO 3 (148.8 mg, 1.2 mmol). The mixture was then stirred at 80° C. for 2 hours under an air atmosphere. After cooling to room temperature, the reaction mixture was washed with 10 mL of saturated Na 2 S 2 o 3 It was washed with aqueous solution, and then extracted three times with ethyl acetate, each time using 10 mL of ethyl acetate. The combined organic layer was extracted three times with ethyl acetate and washed twice with brine, each time the amount of brine was 10 mL, and then washed with Na 2 SO 4 dry. The solvent was removed under reduced pressure, and the residue was purified by flash column chromatography on silica gel to give the desired product III-c....
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