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: 62 percent / SeO2 / dioxane / 10 h / Heating 2: Dess-Martin periodinane; NaHCO3 / CH2Cl2 / 5 h / 20 °C 3: 93.7 mg / p-TsOH*H2O / toluene / 3 h / Heating 4: 86 percent / aq. HBr / 0.83 h / 140 °C View Scheme
参考文献
Organic Letters, , vol. 7, # 14 p. 2989 - 2991
反应条件
1.1: 98 percent / pyridine / 7 h / 3 °C 2.1: 83 percent / 4 Angstroem molecular sieves; tetrabutylammonium acetate; Pd(OAc)2 / acetonitrile / 10 h / 80 °C 3.1: O3; pyridine / CH2Cl2 / -100 °C 3.2: Me2S / CH2Cl2 / 1.5 h / -100 - 20 °C 4.1: NaBH4 / CH2Cl2 / 6 h / -60 - -50 °C 5.1: 62 percent / SeO2 / dioxane / 10 h / Heating 6.1: Dess-Martin periodinane; NaHCO3 / CH2Cl2 / 5 h / 20 °C 7.1: 93.7 mg / p-TsOH*H2O / toluene / 3 h / Heating 8.1: 86 percent / aq. HBr / 0.83 h / 140 °C View Scheme
参考文献
Organic Letters, , vol. 7, # 14 p. 2989 - 2991
反应条件
1: Dess-Martin periodinane; NaHCO3 / CH2Cl2 / 5 h / 20 °C 2: 93.7 mg / p-TsOH*H2O / toluene / 3 h / Heating 3: 86 percent / aq. HBr / 0.83 h / 140 °C View Scheme
参考文献
Organic Letters, , vol. 7, # 14 p. 2989 - 2991
反应条件
1.1: 83 percent / 4 Angstroem molecular sieves; tetrabutylammonium acetate; Pd(OAc)2 / acetonitrile / 10 h / 80 °C 2.1: O3; pyridine / CH2Cl2 / -100 °C 2.2: Me2S / CH2Cl2 / 1.5 h / -100 - 20 °C 3.1: NaBH4 / CH2Cl2 / 6 h / -60 - -50 °C 4.1: 62 percent / SeO2 / dioxane / 10 h / Heating 5.1: Dess-Martin periodinane; NaHCO3 / CH2Cl2 / 5 h / 20 °C 6.1: 93.7 mg / p-TsOH*H2O / toluene / 3 h / Heating 7.1: 86 percent / aq. HBr / 0.83 h / 140 °C View Scheme
参考文献
Organic Letters, , vol. 7, # 14 p. 2989 - 2991
反应条件
1: 93.7 mg / p-TsOH*H2O / toluene / 3 h / Heating 2: 86 percent / aq. HBr / 0.83 h / 140 °C View Scheme
参考文献
Organic Letters, , vol. 7, # 14 p. 2989 - 2991
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: 1) tBuOK / 1) DME, -70 deg C, 20 min, 2a) -70 deg C to room temperature, b) room temperature, 30 h 2: 95 percent / aq. H2SO4 / dioxane / 24 h / 107 °C 3: 90 percent / sodium hexamethyldisilazide / tetrahydrofuran / 16 h / -70 deg C to room temperature 4: 1) O3, 2) Me2S / 1) MeOH, CH2Cl2, O3, -70 deg C, 2) -70 deg C to room temperature, 12 h 5: 94 percent / benzene; methanol; hexane / 3 h 6: 75 percent / p-TsOH / toluene / 4 h / Heating 7: 71 percent / 48percent aq. HBr / 15 h / 140 °C 8: 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: 95 percent / aq. H2SO4 / dioxane / 24 h / 107 °C 2: 90 percent / sodium hexamethyldisilazide / tetrahydrofuran / 16 h / -70 deg C to room temperature 3: 1) O3, 2) Me2S / 1) MeOH, CH2Cl2, O3, -70 deg C, 2) -70 deg C to room temperature, 12 h 4: 94 percent / benzene; methanol; hexane / 3 h 5: 75 percent / p-TsOH / toluene / 4 h / Heating 6: 71 percent / 48percent aq. HBr / 15 h / 140 °C 7: 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: 90 percent / sodium hexamethyldisilazide / tetrahydrofuran / 16 h / -70 deg C to room temperature 2: 1) O3, 2) Me2S / 1) MeOH, CH2Cl2, O3, -70 deg C, 2) -70 deg C to room temperature, 12 h 3: 94 percent / benzene; methanol; hexane / 3 h 4: 75 percent / p-TsOH / toluene / 4 h / Heating 5: 71 percent / 48percent aq. HBr / 15 h / 140 °C 6: 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: 76 percent / acetic acid; dimethylformamide / 2 h / 80 °C 2: 1) 60percent sodium hydride / 1) DMF, 0 deg C, 0.5 h, 2) room temperature, 3 h 3: 100 percent / H2 / Raney Ni / acetic acid / 3 h 4: NaNO2, HOAc / acetic anhydride / 4 h / 0 °C 5: CCl4 / 5 h / Heating 6: 33.5 percent / 1 M H2SO4 / 1,2-dimethoxy-ethane / 24 h / 55 °C 7: 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
