Method for synthesizing pyrrole derivative based on methylene cyclopropane cycloaddition reaction
A technology of methylene cyclopropane and methylene aziridine, applied in the field of preparing 1,2,3-trisubstituted pyrrole derivatives
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Embodiment 1
[0040]
[0041] The reaction was carried out in a 10ml Schlenk reaction tube. After the reactor was evacuated and replaced with argon three times, 5.5mg (10mol%) of catalyst Ni(COD) was added. 2, then add 0.5mmol methylene aziridine 1a and 0.2mmol diyne 2a, add 1ml toluene, and finally react at 25°C for 2 days. After the reaction was completed, the solvent was evaporated by rotary evaporation, and the solid was subjected to silica gel column chromatography, and the column was washed with an eluent of petroleum ether: ethyl acetate = 20:1 to obtain 41 mg of 1,2,3-trisubstituted pyrrole 3a, which was separated and collected. The rate is 60%.
[0042] The characterization data for 1a are as follows:
[0043] 1 HNMR (400MHz, CDCl 3 )7.35–7.24(m,5H),4.72(s,2H),3.69(s,2H),2.13(s,2H);
[0044] 13 CNMR (100MHz, CDCl 3 ) δ 138.3, 137.1, 128.5, 128.3, 127.5, 83.7, 62.9, 30.6.3a are as follows:
[0045] 1 HNMR (400MHz, CDCl 3 )δ7.31-7.20(m,3H),6.92(d,2H),6.32(s,1H),4.92(s,2H)...
Embodiment 2
[0049]
[0050] The reaction was carried out in a 10ml Schlenk reaction tube. After the reactor was evacuated and replaced with argon three times, 5.5mg (10mol%) of catalyst Ni(COD) was added. 2 , then add 0.5mmol methylene aziridine 1a and 0.2mmol diyne 2b, add 1ml toluene, and finally react at 25°C for 2 days. After the reaction was completed, the solvent was evaporated by rotary evaporation, and the solid was subjected to silica gel column chromatography, and the column was washed with an eluent of petroleum ether: ethyl acetate = 20:1 to obtain 41 mg of 1,2,3-trisubstituted pyrrole 3b, which was separated and recovered. The rate is 50%.
[0051] The characterization numbers for 3b are as follows:
[0052] 1 HNMR(400MHz,d6-acetone)δ7.33-7.26(m,3H),7.06(d,2H),6.70(s,1H),5.06(s,2H),4.42(s,2H),4.08(s ,2H),2.86(s,3H),1.99(s,3H),0.19(s,9H); Figure 4 )
[0053] 13 CNMR (100MHz, d6-acetone) δ140.1, 129.4, 127.9, 127.3, 125.8, 121.2, 118.4, 104.1, 90.5, 64.1, 56.8, 50.8, ...
Embodiment 3
[0056]
[0057] The reaction was carried out in a 10ml Schlenk reaction tube. After the reactor was evacuated and replaced with argon three times, 5.5mg (10mol%) of catalyst Ni(COD) was added. 2 , then add 0.5mmol methylene aziridine 1b and 0.2mmol diyne 2a, add 1ml toluene, and finally react at 25°C for 2 days. After the reaction was completed, the solvent was evaporated by rotary evaporation, and the solid was subjected to silica gel column chromatography, and the column was washed with an eluent of petroleum ether: ethyl acetate = 20:1 to obtain 41 mg of 1,2,3-trisubstituted pyrrole 3c, which was separated and recovered. The rate is 55%.
[0058] The single crystal x-diffraction pattern of 3c is as follows: Figure 7 ).
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