Method for preparing indolyl spirocyclic compound through iodine catalyzed multi-component reaction
A multi-component reaction, indole spiro ring technology, applied in the direction of organic chemistry, can solve the problems of polluted environment, corroded equipment, many side reactions, etc., to achieve the effects of simple reaction operation, high catalytic efficiency, and easy availability of raw materials
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Embodiment 1
[0018]
[0019] Accurately weigh 0.1611g N-methylisatin, 0.1121g 1,3-cyclohexanedione, 0.1621g 4-hydroxycoumarin and 0.0254gI 2 Dissolve in 4mL ClCH 2 CH 2 After magnetic stirring at 60° C. for 24 h in Cl, the reaction was determined to be complete by TLC detection, the solvent was removed by rotary evaporation, and a white solid Ia was obtained by column chromatography. Yield 82%, m.p.320.5~321.2℃; 1 HNMR (400MHz, CDCl 3 )δ: 7.88(d, J=7.9Hz, 1H), 7.61~7.56(m, 1H), 7.36(t, J=7.6Hz, 1H), 7.28(d, J=8.1Hz, 2H), 6.96~ 6.92(m,2H),6.88(d,J=7.7Hz,1H),3.38(s,3H),2.86~2.83(m,2H),2.46~2.31(m,2H),2.18~2.02(m, 2H); 13 C NMR (100MHz, CDCl 3 )δ: 195.1, 176.7, 164.9, 158.5, 154.8, 152.6, 145.6, 132.9, 132.1, 129.1, 124.4, 122.7, 122.6, 122.1, 116.8, 114.6, 113.1, 107.9, 106.5, 40.1, 20.0, 397.2 .Anal.Calcd for C 24 h 17 NO 5 : C 72.17, H 4.29, N 3.51; Found: C 72.37, H 4.51, N 3.40.
Embodiment 2
[0021]
[0022] Accurately weigh 0.2373g N-benzyl isatin, 0.1121g 1,3-cyclohexanedione, 0.1621g 4-hydroxycoumarin and 0.0254gI 2 Dissolved in 4 mL of DMF, stirred magnetically at 70°C for 36 hours, detected by TLC, confirmed that the reaction had ended, removed the solvent by rotary evaporation, and obtained white solid Ib by column chromatography, with a yield of 83%, m.p.306.9-307.1°C; 1 H NMR (400MHz, DMSO-d 6 )δ: 8.04(d, J=7.8, Hz, 1H), 7.76(t, J=7.8Hz, 1H), 7.63(d, J=7.5Hz, 2H), 7.52(t, J=7.7Hz, 1H ),7.47(d,J=8.2Hz,1H),7.36(t,J=7.5Hz,2H),7.28(t,J=7.3Hz,1H),7.12(t,J=8.1Hz,1H), 6.88(t, J=7.4Hz, 1H), 6.64(d, J=7.8Hz, 1H), 4.97(ABd, J=16.4Hz, 1H), 4.92(ABd, J=16.4Hz, 1H), 2.96~ 2.93(m,2H),2.42~2.26(m,2H),2.05~1.95(m,2H); 13 C NMR (100MHz, DMSO-d 6 )δ: 195.8, 176.8, 166.2, 158.6, 155.1, 152.3, 145.2, 137.0, 134.1, 132.6, 128.9, 128.8, 127.8, 127.5, 125.5, 123.9, 123.6, 122.4, 117.0, 113.9, 419.5, 18012 ,44.7,37.3,27.4,20.1.Anal.Calcd forC 30 h 21 NO 5 : C 75.78, H 4...
Embodiment 3
[0024]
[0025] Accurately weigh 0.2401g 5-bromo-N-methylisatin, 0.0981g 1,3-cyclopentanedione, 0.1621g 4-hydroxycoumarin and 0.0508g I 2 Dissolve in 4mL CH 2 Cl 2 In the process, after magnetic stirring at 60°C for 24 hours, TLC detection confirmed that the reaction had ended, the solvent was removed by rotary evaporation, and a white solid Ic was obtained by column chromatography with a yield of 79%, m.p.315.1-315.4°C; 1 HNMR (400MHz, DMSO-d 6 )δ:8.07(dd,J=7.9,1.3Hz,1H),7.82~7.77(m,1H),7.57~7.52(m,2H),7.50~7.47(m,2H),7.05(d,J= 8.8Hz, 1H), 3.21(s, 3H), 3.03~3.00(m, 2H), 2.50~2.47(m, 2H); 13 C NMR (100MHz, DMSO-d 6 )δ: 200.5, 177.6, 174.7, 159.2, 157.6, 152.5, 144.5, 134.3, 133.6, 132.1, 127.3, 125.6, 123.6, 117.1, 116.5, 114.5, 113.3, 110.4, 105.3, 46.1, 27.1, 33.1 .Calcd for C 23 h 14 BrNO 5 : C 59.50, H 3.04, N 3.02; Found: C 59.56, H 3.03, N 2.81.
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