hydrogen; palladium on activated charcoal in ethanol T=22°C; P=760 Torr; 6.5 h;

1: With PHT in tetrahydrofuran T=20°C; Bromination; 1 h; 2: With lithium carbonate; lithium bromide in N,N-dimethyl-formamide Aromatisation; 2 h; Heating;

1: 54 percent / dichlorobis(triphenylphosphine)palladium(II) / dioxane / 1.3 h / Heating 2: 98 percent / hydrogen / 5percent Pd/C / ethanol View Scheme

potassium hydroxide

selenium(IV) oxide; ethanol Erwaermen des Reaktionsprodukts mit N-Brom-succinimid in CHCl3;

2: 1.) pyridinium bromide perbromide 2.) LiCl/LiCO3 / 2.) DMF 3: 100 percent / NH2NH2 4: 100 percent / KOH View Scheme

1: Et4NOTs / dimethylformamide / electroreduction 2: 1.) pyridinium bromide perbromide 2.) LiCl/LiCO3 / 2.) DMF 3: 100 percent / NH2NH2 4: 100 percent / KOH View Scheme

1: 1.) pyridinium bromide perbromide 2.) LiCl/LiCO3 / 2.) DMF 2: 100 percent / NH2NH2 3: 100 percent / KOH View Scheme

1.1: n-BuLi; diisopropylamine / tetrahydrofuran; hexane / 0.5 h / -15 - 0 °C 1.2: tetrahydrofuran; hexane / 2 h / -78 - 20 °C 2.1: TiCl4 / CH2Cl2 / 0.17 h / -78 °C 3.1: 63 percent / p-TsOH; 4 Angstroem molecular sieves / benzene / 1 h / Heating 4.1: n-BuLi; diisopropylamine / tetrahydrofuran; hexane / 0.5 h / -15 - 0 °C 4.2: tetrahydrofuran; hexane / 0.5 h / -15 - 20 °C 5.1: MCPBA / hexane / 4 h / 20 °C 5.2: 0.8 g / Et3N*3HF / CH2Cl2 / 2 h / 20 °C 6.1: 88 percent / Dess-Martin periodinane / CH2Cl2 / 1 h / 20 °C 7.1: pyrrolidone hydrotribromide / tetrahydrofuran / 1 h / 20 °C 7.2: 71 percent / LiBr; Li2CO3 / dimethylformamide / 2 h / Heating View Scheme

1.1: n-BuLi; diisopropylamine / tetrahydrofuran; hexane / 0.5 h / -15 - 0 °C 1.2: tetrahydrofuran; hexane / 0.5 h / -15 - 20 °C 2.1: MCPBA / hexane / 4 h / 20 °C 2.2: 0.8 g / Et3N*3HF / CH2Cl2 / 2 h / 20 °C 3.1: 88 percent / Dess-Martin periodinane / CH2Cl2 / 1 h / 20 °C 4.1: pyrrolidone hydrotribromide / tetrahydrofuran / 1 h / 20 °C 4.2: 71 percent / LiBr; Li2CO3 / dimethylformamide / 2 h / Heating View Scheme