1: pyridine / CHCl3 / 0.5 h / 1.) 5 deg C, 1 h; 2.) up to RT, 20 h 2: 72 percent / NaI / butan-2-one / 18 h / Heating 3: 90 percent / H2, Et3N / 5percent Pd/C / methanol / 5 h / 22 °C / 760 Torr 4: 0.4N HCl / 1.) 95 deg C, 90 min; 2.) RT, 30 min 5: pyridine / 20 h / 20 °C View Scheme

1: pyridine / CHCl3 / 0.5 h / 1.) 5 deg C, 1 h; 2.) up to RT, 20 h 2: 72 percent / NaI / butan-2-one / 18 h / Heating 3: 90 percent / H2, Et3N / 5percent Pd/C / methanol / 5 h / 22 °C / 760 Torr 4: 0.4N HCl / 1.) 95 deg C, 90 min; 2.) RT, 30 min 5: pyridine / 20 h / 20 °C 6: 65 percent / CF3SO2OSiMe3, hexamethyldisilazane / CH2Cl2 / 20 h / Ambient temperature 7: 97 percent / CH3ONa / methanol / Ambient temperature View Scheme

1: pyridine / 1 h / Ambient temperature 2: pyridine, 80percent aq. hydrazine / 60 h / Ambient temperature 3: 82 percent / 4-(dimethylamino)pyridine, diethylaminosulfur trifluoride / CH2Cl2 / 18 h / -10 - 20 °C 4: 47 percent / CH3COOH, H2SO4 5: 1.) bis(trimethylsilyl)acetamide, 2.) trimethylsilyl triflate, 3.) 80percent aq. NH2NH2 6: 61 percent / NH3 / methanol / 48 h / Ambient temperature View Scheme

1: pyridine / 1 h / Ambient temperature 2: pyridine, 80percent aq. hydrazine / 60 h / Ambient temperature View Scheme

hydrazine hydrate 1.) solvent: pyridine, 2.) solvent: pyridine; Yield given. Multistep reaction;

1: NaH / dimethylformamide / 13.5 h / Ambient temperature 2: 75 percent / trimethylsilyl trifluoromethanesulfonate (TMSOTf), Et3SiH / CH2Cl2 / 18.5 h / Ambient temperature 3: 97 percent / DMAP, Et3N / CH2Cl2 / 2 h / Ambient temperature 4: 49.5 percent / K2CO3, 18-crown-6 / dimethylformamide / 20 h / 120 °C 5: 78 percent / BCl3 / hexane; CH2Cl2 / 1.) -78 deg C, 2.5 h; 2.) -18 deg C, 4 h View Scheme