1: 90 percent / NaOMe / methanol / 24 h / Ambient temperature 2: 71 percent / pyridine / 1.25 h / Ambient temperature 3: 65 percent / tetrabutylammonium hydroxide, pyridine / acetonitrile / 48 h / Heating 4: 1.) NaH / 1.) DMF, -40 deg C, 0.75 h, 2.) DMF, a) from -40 to -30 deg C, 0.75 h, b) RT, 4 h 5: 71 percent / potassium t-butoxide / CH2Cl2 / 1.5 h / Ambient temperature 6: 40 percent / HCl / CH2Cl2; methanol / 0.75 h / Ambient temperature View Scheme

ammonia in ethanol T=20°C;

ammonia in ethanol T=20°C;

anhydrous magnesium perchlorate; 9-ethyl-3,6-dimethylcarbazole in water; isopropyl alcohol T=0°C; Elimination; deoxygenation; Photolysis;

1: 98 percent / NaOMe / methanol 2: 95 percent / p-toluenesulfonic acid monohydrate / 1,2-dichloro-ethane / 1.33 h / 65 °C 3: 75 percent / NaH / 1,2-dimethoxy-ethane / 1.) r.t., 20 min, 2.) 65 deg C, 18 h 4: 96 percent / 66percent aq. dichloroacetic acid / 3 h / 9 °C 5: 82 percent / PPh3, I2, imidazole / toluene; acetonitrile / 0.5 h / 65 °C 6: 68 percent / aq. ammonium cerium(IV) nitrate / acetonitrile / 3 h / Ambient temperature View Scheme

1: 80 percent / 1 N sodium methylate / methanol / 3 h / 20 °C 2: 1.) acetylsalicylic chloroanhydride, 2.) 0.5 N HCl / 1.) nitromethane, 20 deg C, 15 h, 2.) water, dioxane, 100 deg C, 2.5 h View Scheme

ammonia in ethanol T=20°C;

sodium methylate in methanol

1: 98 percent / Et3N; POCl3 / acetonitrile 2: NH3 / dioxane / 24 h / 20 °C 3: NH3 / methanol View Scheme

1: 5.76 g / sodium methoxide / methanol / 20 °C 2: diphenyl carbonate; sodium hydrogen carbonate / dimethylformamide / 1.5 h / Heating View Scheme