3,9-二甲氧基-5,8,13,13alpha-四氢-6H-异喹啉并[3,2-a]异喹啉-2,10-二醇合成路线 (共 34 条)
反应条件
1: ethanol / 14 h / |Reflux 2: pyridine / dichloromethane / 1.5 h / 0 - 20 °C 3: trichlorophosphate / acetonitrile / 1 h / |Reflux; |Inert atmosphere 4: [[(η6-p-cymene)((1S,2S)-N-p-toluenesulfonyl-1,2-diphenylethylenediamine)]Ru]; formic acid; triethylamine / N,N-dimethyl-formamide / 20 °C 5: water; sodium hydroxide / ethanol / 3 h / 20 °C 6: thionyl chloride / dichloromethane / 1.5 h / 0 - 20 °C 7: sodium hydrogencarbonate / dichloromethane / 1.5 h / 20 °C 8: hydrogenchloride / water; ethanol / 2 h / |Reflux View Scheme
参考文献
Bioorganic and Medicinal Chemistry, , vol. 21, # 4 p. 856 - 868
反应条件
1.1: acetic acid; bromine / 2 h / 20 °C 2.1: potassium carbonate / acetone / |Reflux 3.1: potassium hydroxide; water; copper; copper(II) oxide / 1 h / 140 °C / |Inert atmosphere; |Microwave irradiation 4.1: 3,4,5-trimethoxyphenylboronic acid / toluene / 1 h / |Reflux; |Dean-Stark 4.2: 46 h / 100 °C / |Molecular sieve; |Sealed tube 4.3: 2 h / |Reflux 5.1: potassium carbonate / acetone / 4 h / |Reflux 6.1: ethanol / 14 h / |Reflux 7.1: pyridine / dichloromethane / 1.5 h / 0 - 20 °C 8.1: trichlorophosphate / acetonitrile / 1 h / |Reflux; |Inert atmosphere 9.1: [[(η6-p-cymene)((1S,2S)-N-p-toluenesulfonyl-1,2-diphenylethylenediamine)]Ru]; formic acid; triethylamine / N,N-dimethyl-formamide / 20 °C 10.1: water; sodium hydroxide / ethanol / 3 h / 20 °C 11.1: thionyl chloride / dichloromethane / 1.5 h / 0 - 20 °C 12.1: sodium hydrogencarbonate / dichloromethane / 1.5 h / 20 °C 13.1: hydrogenchloride / water; ethanol / 2 h / |Reflux View Scheme
参考文献
Bioorganic and Medicinal Chemistry, , vol. 21, # 4 p. 856 - 868
反应条件
1.1: potassium carbonate / acetone / |Reflux 2.1: potassium hydroxide; water; copper; copper(II) oxide / 1 h / 140 °C / |Inert atmosphere; |Microwave irradiation 3.1: 3,4,5-trimethoxyphenylboronic acid / toluene / 1 h / |Reflux; |Dean-Stark 3.2: 46 h / 100 °C / |Molecular sieve; |Sealed tube 3.3: 2 h / |Reflux 4.1: potassium carbonate / acetone / 4 h / |Reflux 5.1: ethanol / 14 h / |Reflux 6.1: pyridine / dichloromethane / 1.5 h / 0 - 20 °C 7.1: trichlorophosphate / acetonitrile / 1 h / |Reflux; |Inert atmosphere 8.1: [[(η6-p-cymene)((1S,2S)-N-p-toluenesulfonyl-1,2-diphenylethylenediamine)]Ru]; formic acid; triethylamine / N,N-dimethyl-formamide / 20 °C 9.1: water; sodium hydroxide / ethanol / 3 h / 20 °C 10.1: thionyl chloride / dichloromethane / 1.5 h / 0 - 20 °C 11.1: sodium hydrogencarbonate / dichloromethane / 1.5 h / 20 °C 12.1: hydrogenchloride / water; ethanol / 2 h / |Reflux View Scheme
参考文献
Bioorganic and Medicinal Chemistry, , vol. 21, # 4 p. 856 - 868
反应条件
1: potassium carbonate / acetone / 4 h / |Reflux 2: acetic acid; ammonium acetate / 100 °C 3: lithium aluminium tetrahydride / tetrahydrofuran / 2 h / |Reflux 4: ethanol / 14 h / |Reflux 5: pyridine / dichloromethane / 1.5 h / 0 - 20 °C 6: trichlorophosphate / acetonitrile / 1 h / |Reflux; |Inert atmosphere 7: [[(η6-p-cymene)((1S,2S)-N-p-toluenesulfonyl-1,2-diphenylethylenediamine)]Ru]; formic acid; triethylamine / N,N-dimethyl-formamide / 20 °C 8: water; sodium hydroxide / ethanol / 3 h / 20 °C 9: thionyl chloride / dichloromethane / 1.5 h / 0 - 20 °C 10: sodium hydrogencarbonate / dichloromethane / 1.5 h / 20 °C 11: hydrogenchloride / water; ethanol / 2 h / |Reflux View Scheme
参考文献
Bioorganic and Medicinal Chemistry, , vol. 21, # 4 p. 856 - 868
反应条件
1.1: potassium hydroxide; water; copper; copper(II) oxide / 1 h / 140 °C / |Inert atmosphere; |Microwave irradiation 2.1: 3,4,5-trimethoxyphenylboronic acid / toluene / 1 h / |Reflux; |Dean-Stark 2.2: 46 h / 100 °C / |Molecular sieve; |Sealed tube 2.3: 2 h / |Reflux 3.1: potassium carbonate / acetone / 4 h / |Reflux 4.1: ethanol / 14 h / |Reflux 5.1: pyridine / dichloromethane / 1.5 h / 0 - 20 °C 6.1: trichlorophosphate / acetonitrile / 1 h / |Reflux; |Inert atmosphere 7.1: [[(η6-p-cymene)((1S,2S)-N-p-toluenesulfonyl-1,2-diphenylethylenediamine)]Ru]; formic acid; triethylamine / N,N-dimethyl-formamide / 20 °C 8.1: water; sodium hydroxide / ethanol / 3 h / 20 °C 9.1: thionyl chloride / dichloromethane / 1.5 h / 0 - 20 °C 10.1: sodium hydrogencarbonate / dichloromethane / 1.5 h / 20 °C 11.1: hydrogenchloride / water; ethanol / 2 h / |Reflux View Scheme
参考文献
Bioorganic and Medicinal Chemistry, , vol. 21, # 4 p. 856 - 868
反应条件
1.1: 3,4,5-trimethoxyphenylboronic acid / toluene / 1 h / |Reflux; |Dean-Stark 1.2: 46 h / 100 °C / |Molecular sieve; |Sealed tube 1.3: 2 h / |Reflux 2.1: potassium carbonate / acetone / 4 h / |Reflux 3.1: ethanol / 14 h / |Reflux 4.1: pyridine / dichloromethane / 1.5 h / 0 - 20 °C 5.1: trichlorophosphate / acetonitrile / 1 h / |Reflux; |Inert atmosphere 6.1: [[(η6-p-cymene)((1S,2S)-N-p-toluenesulfonyl-1,2-diphenylethylenediamine)]Ru]; formic acid; triethylamine / N,N-dimethyl-formamide / 20 °C 7.1: water; sodium hydroxide / ethanol / 3 h / 20 °C 8.1: thionyl chloride / dichloromethane / 1.5 h / 0 - 20 °C 9.1: sodium hydrogencarbonate / dichloromethane / 1.5 h / 20 °C 10.1: hydrogenchloride / water; ethanol / 2 h / |Reflux View Scheme
参考文献
Bioorganic and Medicinal Chemistry, , vol. 21, # 4 p. 856 - 868
反应条件
1: potassium carbonate / acetone / 4 h / |Reflux 2: ethanol / 14 h / |Reflux 3: pyridine / dichloromethane / 1.5 h / 0 - 20 °C 4: trichlorophosphate / acetonitrile / 1 h / |Reflux; |Inert atmosphere 5: [[(η6-p-cymene)((1S,2S)-N-p-toluenesulfonyl-1,2-diphenylethylenediamine)]Ru]; formic acid; triethylamine / N,N-dimethyl-formamide / 20 °C 6: water; sodium hydroxide / ethanol / 3 h / 20 °C 7: thionyl chloride / dichloromethane / 1.5 h / 0 - 20 °C 8: sodium hydrogencarbonate / dichloromethane / 1.5 h / 20 °C 9: hydrogenchloride / water; ethanol / 2 h / |Reflux View Scheme
参考文献
Bioorganic and Medicinal Chemistry, , vol. 21, # 4 p. 856 - 868
反应条件
1: pyridine / dichloromethane / 1.5 h / 0 - 20 °C 2: trichlorophosphate / acetonitrile / 1 h / |Reflux; |Inert atmosphere 3: [[(η6-p-cymene)((1S,2S)-N-p-toluenesulfonyl-1,2-diphenylethylenediamine)]Ru]; formic acid; triethylamine / N,N-dimethyl-formamide / 20 °C 4: water; sodium hydroxide / ethanol / 3 h / 20 °C 5: thionyl chloride / dichloromethane / 1.5 h / 0 - 20 °C 6: sodium hydrogencarbonate / dichloromethane / 1.5 h / 20 °C 7: hydrogenchloride / water; ethanol / 2 h / |Reflux View Scheme
参考文献
Bioorganic and Medicinal Chemistry, , vol. 21, # 4 p. 856 - 868
反应条件
1: acetic acid; ammonium acetate / 100 °C 2: lithium aluminium tetrahydride / tetrahydrofuran / 2 h / |Reflux 3: ethanol / 14 h / |Reflux 4: pyridine / dichloromethane / 1.5 h / 0 - 20 °C 5: trichlorophosphate / acetonitrile / 1 h / |Reflux; |Inert atmosphere 6: [[(η6-p-cymene)((1S,2S)-N-p-toluenesulfonyl-1,2-diphenylethylenediamine)]Ru]; formic acid; triethylamine / N,N-dimethyl-formamide / 20 °C 7: water; sodium hydroxide / ethanol / 3 h / 20 °C 8: thionyl chloride / dichloromethane / 1.5 h / 0 - 20 °C 9: sodium hydrogencarbonate / dichloromethane / 1.5 h / 20 °C 10: hydrogenchloride / water; ethanol / 2 h / |Reflux View Scheme
参考文献
Bioorganic and Medicinal Chemistry, , vol. 21, # 4 p. 856 - 868
反应条件
1: trichlorophosphate / acetonitrile / 1 h / |Reflux; |Inert atmosphere 2: [[(η6-p-cymene)((1S,2S)-N-p-toluenesulfonyl-1,2-diphenylethylenediamine)]Ru]; formic acid; triethylamine / N,N-dimethyl-formamide / 20 °C 3: water; sodium hydroxide / ethanol / 3 h / 20 °C 4: thionyl chloride / dichloromethane / 1.5 h / 0 - 20 °C 5: sodium hydrogencarbonate / dichloromethane / 1.5 h / 20 °C 6: hydrogenchloride / water; ethanol / 2 h / |Reflux View Scheme
参考文献
Bioorganic and Medicinal Chemistry, , vol. 21, # 4 p. 856 - 868