aluminum oxide in toluene 16 h; Heating / reflux;

Raney nickel W-5; hydrogen in ethanol P=3040 Torr; 16 h; Ambient temperature;

sodium tetrahydroborate; nickel dichloride in methanol

1: 90 percent / TFA / CH2Cl2 / 20 °C 2: 42 percent / hydrogen / Pd/C / ethanol / 4 h / 20 °C / 760 Torr View Scheme

in diethyl ether T=20°C; Friedel-Crafts cyclization; 0.5 h;

1: 1.) p-toluenesulfonic acid, 2.) 10percent NaOH / 1.) toluene, reflux, 3 h, 2.) reflux, 2 h 2: 37 percent / 1.) N-bromosuccinimide, 2.) NH3 / 1.) CCl4, reflux, 48 h, 2.) THF, 3 h 3: 16 percent / NH3 / tetrahydrofuran / 3 h 4: 65 percent / 1 M NH4OH / 1 h / 70 °C 5: 59 percent / H2, Raney nickel W-5 / ethanol / 16 h / 3040 Torr / Ambient temperature View Scheme

1: 37 percent / 1.) N-bromosuccinimide, 2.) NH3 / 1.) CCl4, reflux, 48 h, 2.) THF, 3 h 2: 16 percent / NH3 / tetrahydrofuran / 3 h 3: 65 percent / 1 M NH4OH / 1 h / 70 °C 4: 59 percent / H2, Raney nickel W-5 / ethanol / 16 h / 3040 Torr / Ambient temperature View Scheme

1: 240 g / Zn / benzene / Heating 2: 1.) p-toluenesulfonic acid, 2.) 10percent NaOH / 1.) toluene, reflux, 3 h, 2.) reflux, 2 h 3: 37 percent / 1.) N-bromosuccinimide, 2.) NH3 / 1.) CCl4, reflux, 48 h, 2.) THF, 3 h 4: 16 percent / NH3 / tetrahydrofuran / 3 h 5: 65 percent / 1 M NH4OH / 1 h / 70 °C 6: 59 percent / H2, Raney nickel W-5 / ethanol / 16 h / 3040 Torr / Ambient temperature View Scheme

1.1: cesium fluoride; tetrabutyl-ammonium chloride; bis-triphenylphosphine-palladium(II) chloride / toluene; water / 18 h / 20 °C / |Inert atmosphere 2.1: acetic acid / chloroform / 1 h / 0 - 20 °C 2.2: 20 °C 3.1: trifluoroacetic acid / 1,2-dichloro-ethane / 2 h / 80 °C 4.1: nickel dichloride; sodium tetrahydroborate / methanol; tetrahydrofuran / 1 h / 0 - 20 °C View Scheme

formic acid; hydroxylamine-o-sulphonic acid 10 h; Heating;