Tetrahydroisoquinoline derivative as well as preparation method and application thereof
A technology of tetrahydroisoquinoline and derivatives, which is applied in the direction of drug combinations, pharmaceutical formulas, and medical preparations containing active ingredients, etc., can solve the problems of many steps in the synthesis process, unstable raw materials, inconvenient operation, etc., and achieve reaction Few steps, good anti-cancer effect, low cost effect
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Embodiment 1
[0057]
[0058] C, N-cyclomethanimine (0.2mmol), p-toluidine (0.3mmol) and Rh 2 (OAc) 4 (5.0mol%) was dissolved in a test tube containing 2.0mL methyl tert-butyl ether, stirred at a specific temperature (25°C), and then diazo (0.5mmol) methyl tert-butyl ether (1.0mL ) solution was added to the above-mentioned mixed solution through a peristaltic pump, and the addition was completed in one hour, and the reaction was continued for two hours. After the C,N-cyclomethanimine reaction was completed, the solvent was removed by rotary evaporation under reduced pressure to obtain a crude product. The crude product was purified by column chromatography (ethyl acetate:petroleum ether=1:50-1:6) to obtain a pair of diastereoisomers, the total yield: 62%, dr value: 85:15.
[0059] 1 H NMR (400MHz, CDCl 3 )δ7.80–7.72(m,2H),7.47(d,J=6.8Hz,1H),7.43–7.33(m,2H),7.30–7.23(m,1H),7.19–7.09(m,2H) ,7.06(d,J=6.5Hz,1H),6.86(d,J=7.4Hz,2H),6.41(d,J=7.5Hz,2H),5.17–5.05(m,1H),4.37–4.24( m,1H),3.92–...
Embodiment 2
[0061]
[0062] C, N-cyclomethanimine (0.2mmol), p-fluoroaniline (0.3mmol) and Rh 2 (OAc) 4 (5.0mol%) was dissolved in a test tube containing 2.0mL methyl tert-butyl ether, stirred at a specific temperature (25°C), and then diazo (0.5mmol) methyl tert-butyl ether (1.0mL ) solution was added to the above-mentioned mixed solution through a peristaltic pump, and the addition was completed in one hour, and the reaction was continued for two hours. After the C,N-cyclomethanimine reaction was completed, the solvent was removed by rotary evaporation under reduced pressure to obtain a crude product. The crude product was purified by column chromatography (ethyl acetate:petroleum ether=1:50-1:6) to obtain a pair of diastereoisomers, the total yield: 73%, dr value: 84:16.
[0063] 1 H NMR (500MHz, Acetone) δ9.03 (s, 1H), 7.87 (d, J=7.6Hz, 2H), 7.58–7.51 (m, 1H), 7.51–7.43 (m, 3H), 7.27–7.19 ( m,1H),7.19–7.09(m,2H),6.82–6.72(m,2H),6.59–6.51(m,2H),5.95(d,J=9.8Hz,1H),5.11–5.00(m, 1H...
Embodiment 3
[0065]
[0066] C, N-cyclomethanimine (0.2mmol), p-chloroaniline (0.3mmol) and Rh 2 (OAc) 4 (5.0mol%) was dissolved in a test tube containing 2.0mL methyl tert-butyl ether, stirred at a specific temperature (25°C), and then diazo (0.5mmol) methyl tert-butyl ether (1.0mL ) solution was added to the above-mentioned mixed solution through a peristaltic pump, and the addition was completed in one hour, and the reaction was continued for two hours. After the C,N-cyclomethanimine reaction was completed, the solvent was removed by rotary evaporation under reduced pressure to obtain a crude product. The crude product was purified by column chromatography (ethyl acetate:petroleum ether=1:50-1:6) to obtain a pair of diastereoisomers, the total yield: 85%, dr value: 86:14.
[0067] 1 H NMR (400MHz, CDCl 3 )δ7.74(d,J=7.5Hz,2H),7.54–7.38(m,4H),7.29(d,J=7.3Hz,1H),7.22–7.13(m,2H),7.09(d,J =7.1Hz,1H),6.99(d,J=8.5Hz,2H),6.56–6.34(m,2H),5.58–5.35(m,1H),5.17–4.97(m,1H),4.37–4.21( m,1H),3...
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