A method for synthesizing four-substituted nh-pyrroles
A technology of ketone compounds and compounds, which is applied in the field of synthesis of tetrasubstituted NH-pyrrole compounds, and achieves the effects of high yield, simple post-treatment and few reaction steps
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Embodiment 1
[0021]
[0022] Into a 25mL reaction tube were added chalcone (0.0520g, 0.25mmol), diethyl iminodiacetate (0.0945g, 0.5mmol), Et 3 N (0.0253g, 0.25mmol) and Cu(OAc) 2 (0.0498 g, 0.25 mmol), then reacted in DMF (1.0 mL) at 100 °C for 8 h. After the reaction was detected by TLC, it was extracted with 10 mL of saturated aqueous sodium chloride solution and ethyl acetate (3×10 mL), the organic layers were combined and dried over anhydrous sodium sulfate, the solvent was removed with a rotary evaporator, and finally the column layer was carried out. (The eluent is a mixture of petroleum ether and ethyl acetate with a volume ratio of 2:1) to obtain the target compound with a yield of 90%, which is a white solid.
[0023] Characterization data: 1 H NMR (500MHz, CDCl 3 )δ10.13(s, 1H), 7.79(d, J=7.5Hz, 2H), 7.49(t, J=7.5Hz, 1H), 7.36(t, J=8.0Hz, 2H), 7.30–7.29( m, 2H), 7.22–7.20 (m, 3H), 4.25 (q, J=7.0Hz, 2H), 4.09 (q, J=7.0Hz, 2H), 1.18 (t, J=7.5Hz, 3H), 0.91(t,J=7.0Hz,3H); 1...
Embodiment 2
[0025]
[0026] Into a 25mL reaction tube were added (E)-1-(4-bromophenyl)-3-phenylprop-2-en-1-one (0.0718g, 0.25mmol), diethyl iminodiacetate (0.0945 g, 0.5mmol), Et 3 N (0.0253 g, 0.25 mmol) and Cu (NO 3 ) 2 (0.0468 g, 0.25 mmol), then reacted in DMF (1.0 mL) at 100 °C for 8 h. After the reaction was detected by TLC, it was extracted with 10 mL of saturated aqueous sodium chloride solution and ethyl acetate (3×10 mL), the organic layers were combined and dried over anhydrous sodium sulfate, the solvent was removed with a rotary evaporator, and finally the column layer was carried out. (The eluent is a mixture of petroleum ether and ethyl acetate with a volume ratio of 2:1) to obtain the target compound with a yield of 81%, which is a yellow solid.
[0027] Characterization data: 1 H NMR (500MHz, CDCl 3 )δ9.96(s,1H),7.58–7.55(m,2H),7.44–7.42(m,2H),7.20(d,J=2.0Hz,1H),7.18(d,J=3.0Hz,1H) ),7.17–7.15(m,3H),4.18(q,J=7.0Hz,2H),4.06(q,J=7.5Hz,2H),1.12(t,J=7.0Hz,3H),0.93(t ...
Embodiment 3
[0029]
[0030] Into a 25mL reaction tube were added (E)-1-(4-nitrophenyl)-3-phenylprop-2-en-1-one (0.0575g, 0.25mmol), diethyl iminodiacetate ( 0.0945g, 0.5mmol), Et 3 N (0.0253 g, 0.25 mmol) and CuCl (0.0250 g, 0.25 mmol) were then reacted in DMF (1.0 mL) at 100° C. for 8 h. After the reaction was detected by TLC, it was extracted with 10 mL of saturated aqueous sodium chloride solution and ethyl acetate (3×10 mL), the organic layers were combined and dried over anhydrous sodium sulfate, the solvent was removed with a rotary evaporator, and finally the column layer was carried out. analyte and separated (the eluent is a mixture of petroleum ether and ethyl acetate with a volume ratio of 2:1) to obtain the target compound with a yield of 88%, which is a red solid.
[0031] Characterization data: 1 H NMR (500MHz, CDCl 3 )δ10.05(s,1H),8.11(d,J=8.5Hz,2H),7.83(d,J=9.0Hz,2H),7.17–7.15(m,2H),7.15–7.12(m,3H) ), 4.19(d, J=7.0Hz, 2H), 4.07(q, J=7.0Hz, 2H), 1.10(t, J=7.0Hz, 3H),...
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