3-chloro-benzenecarboperoxoic acid in tetrahydrofuran 3 h; Ambient temperaturein the dark;

ammonia in tetrahydrofuran; methanol 1.5 h;

1: 0.5 g / 0.5 h / 260 - 280 °C 2: 83 percent / 10percent Pd/C / various solvent(s) / 8 h / 190 °C 3: 1.) Na, NH3 liq., 2.) AcOH / 1.) THF, 18 h, 2.) 100 deg C to 125 deg C, 18 h 4: 1.) t-BuONa, 2.) DDQ / 1.) t-BuOH, reflux, 15 h, 2.) dioxane, reflux, 15 h 5: 29 mg / I2 / benzene / 12 h / Heating 6: 5percent aq. NaOH / tetrahydrofuran; methanol / 8 h / Ambient temperature 7: pyridine 8: 1.) AIBN, dibromantin, 2.) Li2CO3, LiF / 1.) CCl4, reflux, 30 min, 2.) HMPA, 100 deg C, 3 h 9: 76 percent / NH3 / methanol; tetrahydrofuran / 1.5 h View Scheme

1: 0.5 g / 0.5 h / 260 - 280 °C 2: 83 percent / 10percent Pd/C / various solvent(s) / 8 h / 190 °C 3: 1.) Na, NH3 liq., 2.) AcOH / 1.) THF, 18 h, 2.) 100 deg C to 125 deg C, 18 h 4: 1.) t-BuONa, 2.) DDQ / 1.) t-BuOH, reflux, 15 h, 2.) dioxane, reflux, 15 h 5: 29 mg / I2 / benzene / 12 h / Heating 6: 5percent aq. NaOH / tetrahydrofuran; methanol / 8 h / Ambient temperature 7: pyridine 8: 1.) AIBN, dibromantin, 2.) Li2CO3, LiF / 1.) CCl4, reflux, 30 min, 2.) HMPA, 100 deg C, 3 h 9: 76 percent / NH3 / methanol; tetrahydrofuran / 1.5 h View Scheme

1: 83 percent / 10percent Pd/C / various solvent(s) / 8 h / 190 °C 2: 1.) Na, NH3 liq., 2.) AcOH / 1.) THF, 18 h, 2.) 100 deg C to 125 deg C, 18 h 3: 1.) t-BuONa, 2.) DDQ / 1.) t-BuOH, reflux, 15 h, 2.) dioxane, reflux, 15 h 4: 29 mg / I2 / benzene / 12 h / Heating 5: 5percent aq. NaOH / tetrahydrofuran; methanol / 8 h / Ambient temperature 6: pyridine 7: 1.) AIBN, dibromantin, 2.) Li2CO3, LiF / 1.) CCl4, reflux, 30 min, 2.) HMPA, 100 deg C, 3 h 8: 76 percent / NH3 / methanol; tetrahydrofuran / 1.5 h View Scheme

1: 1.) Na, NH3 liq., 2.) AcOH / 1.) THF, 18 h, 2.) 100 deg C to 125 deg C, 18 h 2: 1.) t-BuONa, 2.) DDQ / 1.) t-BuOH, reflux, 15 h, 2.) dioxane, reflux, 15 h 3: 29 mg / I2 / benzene / 12 h / Heating 4: 5percent aq. NaOH / tetrahydrofuran; methanol / 8 h / Ambient temperature 5: pyridine 6: 1.) AIBN, dibromantin, 2.) Li2CO3, LiF / 1.) CCl4, reflux, 30 min, 2.) HMPA, 100 deg C, 3 h 7: 76 percent / NH3 / methanol; tetrahydrofuran / 1.5 h View Scheme

1: 1.) t-BuONa, 2.) DDQ / 1.) t-BuOH, reflux, 15 h, 2.) dioxane, reflux, 15 h 2: 1.) Na, liq. NH3, EtOH, 2.) AcOH / 1.) THF, 18 h, 2.) 100 deg C, overnight 3: 1.) t-BuONa, 2.) DDQ / 1.) t-BuOH, reflux, 18 h, 2.) dioxane, reflux, 3 h 4: 29 mg / I2 / benzene / 12 h / Heating 5: 5percent aq. NaOH / tetrahydrofuran; methanol / 8 h / Ambient temperature 6: pyridine 7: 1.) AIBN, dibromantin, 2.) Li2CO3, LiF / 1.) CCl4, reflux, 30 min, 2.) HMPA, 100 deg C, 3 h 8: 76 percent / NH3 / methanol; tetrahydrofuran / 1.5 h View Scheme

1: 1.) t-BuONa, 2.) DDQ / 1.) t-BuOH, reflux, 18 h, 2.) dioxane, reflux, 3 h 2: 1.) Na, liq. NH3, EtOH, 2.) AcOH / 1.) THF, 18 h, 2.) 100 deg C, overnight 3: 1.) t-BuONa, 2.) DDQ / 1.) t-BuOH, reflux, 15 h, 2.) dioxane, reflux, 15 h 4: 29 mg / I2 / benzene / 12 h / Heating 5: 5percent aq. NaOH / tetrahydrofuran; methanol / 8 h / Ambient temperature 6: pyridine 7: 1.) AIBN, dibromantin, 2.) Li2CO3, LiF / 1.) CCl4, reflux, 30 min, 2.) HMPA, 100 deg C, 3 h 8: 76 percent / NH3 / methanol; tetrahydrofuran / 1.5 h View Scheme

1: pyridine 2: 1.) AIBN, dibromantin, 2.) Li2CO3, LiF / 1.) CCl4, reflux, 30 min, 2.) HMPA, 100 deg C, 3 h 3: 76 percent / NH3 / methanol; tetrahydrofuran / 1.5 h View Scheme

1: 29 mg / I2 / benzene / 12 h / Heating 2: 5percent aq. NaOH / tetrahydrofuran; methanol / 8 h / Ambient temperature 3: pyridine 4: 1.) AIBN, dibromantin, 2.) Li2CO3, LiF / 1.) CCl4, reflux, 30 min, 2.) HMPA, 100 deg C, 3 h 5: 76 percent / NH3 / methanol; tetrahydrofuran / 1.5 h View Scheme