1: acetyl chloride With AlCl3, aluminium chloride in chloroform T=0°C; 0.166667 h; 2: N-(n-butyl)carbazole in chloroform T=0 - 20°C; 3.25 h;

N-bromosuccinmide in chloroform

bromine; acetic acid

1: dibenzopyrrole With potassium hydroxide in dimethyl sulfoxide T=20°C; 0.333333 h; 2: 1-bromo-butane in dimethyl sulfoxide T=35°C; 0.1 h; Sonication; Solvent;

sodium hydroxide in acetone 16 h; RefluxInert atmosphere;

p-methylnitrobenzene T=160°C; 5 h; Inert atmosphere;

copper(l) iodide; copper diacetate; sodium carbonate; ethylene glycol in isopropyl alcohol T=85°C; Ullmann Condensation; 16 h; Inert atmosphere;

1: 1.) 50percent aq. NaOH / 1.) DMSO, 20 deg C, 5 min, 2.) from 35 deg C to 40 deg C, 2 h 2: 1.) n-BuLi / 1.) THF, -78 deg C, 5 min, 2.) -78 deg C, 0.5 h 3: 86 percent / H2 / W-2 Raney nickel / aq. ethanol / 5 h / Heating View Scheme

1: 1.) n-BuLi / 1.) THF, -78 deg C, 5 min, 2.) -78 deg C, 0.5 h 2: 86 percent / H2 / W-2 Raney nickel / aq. ethanol / 5 h / Heating View Scheme

1.1: potassium phosphate; tetrakis(triphenylphosphine) palladium(0) / ethanol / 6 h / |Reflux; |Inert atmosphere 2.1: hydrazine hydrate / methanol / 2 h / 20 °C 3.1: hydrogenchloride; sodium nitrite / tetrahydrofuran; water / 0.33 h / |Cooling with ice 3.2: 20 °C / |Cooling with ice 4.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 1 h / 20 °C 5.1: copper(l) iodide; copper diacetate; sodium carbonate; ethylene glycol / isopropyl alcohol / 16 h / 85 °C / |Inert atmosphere View Scheme