T=260 - 280°C; 0.5 h;

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 View Scheme

hydrogenchloride; 1,3-dibromo-5,5-dimethyl-hydantoin; 2,2'-azo-bisisobutyronitrile 1.) CCl4, reflux, 2 h, 2.) THF, overnight; Yield given. Multistep reaction. Yields of byproduct given;

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 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 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 View Scheme

palladium on activated charcoal in various solvent(s) T=190°C; 8 h;

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