4-乙基-4-羟基-3,4,12,14-四氢-1H-吡喃并[3'4':6,7]吲哚嗪并[1,2-b]喹啉-3,14-二酮合成路线 （共 79 条）
反应条件
1: 1) 60percent sodium hydride / 1) DMF, 0 deg C, 0.5 h, 2) room temperature, 3 h 2: 100 percent / H2 / Raney Ni / acetic acid / 3 h 3: NaNO2, HOAc / acetic anhydride / 4 h / 0 °C 4: CCl4 / 5 h / Heating 5: 33.5 percent / 1 M H2SO4 / 1,2-dimethoxy-ethane / 24 h / 55 °C 6: 69.5 percent / 2) p-TsOH / toluene / Heating; 1) 30 min, 2) 3 h View Scheme
参考文献
Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), , # 1 p. 27 - 31
反应条件
1: 100 percent / H2 / Raney Ni / acetic acid / 3 h 2: NaNO2, HOAc / acetic anhydride / 4 h / 0 °C 3: CCl4 / 5 h / Heating 4: 33.5 percent / 1 M H2SO4 / 1,2-dimethoxy-ethane / 24 h / 55 °C 5: 69.5 percent / 2) p-TsOH / toluene / Heating; 1) 30 min, 2) 3 h View Scheme
参考文献
Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), , # 1 p. 27 - 31
反应条件
1: 58 percent / LDA 2: 84 percent / DEAD, PPh3 / tetrahydrofuran / Ambient temperature 3: 59 percent / Pd(OAc)2, KOAc / acetonitrile View Scheme
参考文献
Journal of Organic Chemistry, , vol. 59, # 18 p. 5120 - 5121
反应条件
1: 2.) p-toluenesulfonic acid / 1.) toluene, ref;ux, 30 min, 2.) toluene, reflux, 3 h 2: 41 percent / O2, cupric chloride, dimethylamine / dimethylformamide; H2O View Scheme
参考文献
Journal of Medicinal Chemistry, , vol. 23, # 5 p. 554 - 560
反应条件
1: 2.) p-toluenesulfonic acid / 1.) toluene, ref;ux, 30 min, 2.) toluene, reflux, 3 h 2: 41 percent / O2, cupric chloride, dimethylamine / dimethylformamide; H2O View Scheme
参考文献
Journal of Medicinal Chemistry, , vol. 23, # 5 p. 554 - 560
反应条件
1: 88 percent / H2SO4 / 1,2-dimethoxy-ethane / 24 h / 50 °C 2: 2.) p-toluenesulfonic acid / 1.) toluene, ref;ux, 30 min, 2.) toluene, reflux, 3 h 3: 41 percent / O2, cupric chloride, dimethylamine / dimethylformamide; H2O View Scheme
参考文献
Journal of Medicinal Chemistry, , vol. 23, # 5 p. 554 - 560
反应条件
1: NaNO2 / acetic anhydride; acetic acid / 2 h / 0 °C 2: CCl4 / Heating 3: 88 percent / H2SO4 / 1,2-dimethoxy-ethane / 24 h / 50 °C 4: 2.) p-toluenesulfonic acid / 1.) toluene, ref;ux, 30 min, 2.) toluene, reflux, 3 h 5: 41 percent / O2, cupric chloride, dimethylamine / dimethylformamide; H2O View Scheme
参考文献
Journal of Medicinal Chemistry, , vol. 23, # 5 p. 554 - 560
反应条件
1: CCl4 / Heating 2: 88 percent / H2SO4 / 1,2-dimethoxy-ethane / 24 h / 50 °C 3: 2.) p-toluenesulfonic acid / 1.) toluene, ref;ux, 30 min, 2.) toluene, reflux, 3 h 4: 41 percent / O2, cupric chloride, dimethylamine / dimethylformamide; H2O View Scheme
参考文献
Journal of Medicinal Chemistry, , vol. 23, # 5 p. 554 - 560
反应条件
1: 92 percent / Et3N / ethanol / 65 h / Ambient temperature 2: 1) tBuOK / 1) DME, -70 deg C, 20 min, 2a) -70 deg C to room temperature, b) room temperature, 30 h 3: 95 percent / aq. H2SO4 / dioxane / 24 h / 107 °C 4: 90 percent / sodium hexamethyldisilazide / tetrahydrofuran / 16 h / -70 deg C to room temperature 5: 1) O3, 2) Me2S / 1) MeOH, CH2Cl2, O3, -70 deg C, 2) -70 deg C to room temperature, 12 h 6: 94 percent / benzene; methanol; hexane / 3 h 7: 75 percent / p-TsOH / toluene / 4 h / Heating 8: 71 percent / 48percent aq. HBr / 15 h / 140 °C 9: 91 percent / O2, CuCl2, dimethylamine / dimethylformamide / 7 h View Scheme
参考文献
Journal of Organic Chemistry, , vol. 58, # 3 p. 611 - 617
反应条件
1: 84 percent / DEAD, PPh3 / tetrahydrofuran / Ambient temperature 2: 59 percent / Pd(OAc)2, KOAc / acetonitrile View Scheme
参考文献
Journal of Organic Chemistry, , vol. 59, # 18 p. 5120 - 5121
