1: Ozonolyse 2: aqueous HCl View Scheme

tris(triphenylphosphine)ruthenium(II) chloride in 1,4-dioxane T=180°C; 20 h;

ammonium cerium (IV) nitrate in methanol Fischer indole synthesis; 1.5 h; Reflux;

FeBr2 in toluene T=140°C; 16 h; Schlenk techniqueInert atmosphere;

toluene-4-sulfonic acid in ethanol Fischer cyclization; 1 h; Heating;

aluminium trichloride; 1-butylpyridinium chloride Fischer indole synthesis; 0.75 h; Heating;

zinc(II) chloride T=170°C;

1: sodium hydride / N,N-dimethyl-formamide / 3 h / 0 - 20 °C / |Inert atmosphere 2: palladium 10 on activated carbon; hydrogen / methanol / 20 °C / |Inert atmosphere 3: 1,1-dimethylnitroethane; trimethylsilylazide / acetonitrile / 2 h / 20 °C / |Inert atmosphere; |Cooling 4: FeBr2 / toluene / 16 h / 140 °C / |Schlenk technique; |Inert atmosphere View Scheme

1: palladium 10 on activated carbon; hydrogen / methanol / 20 °C / |Inert atmosphere 2: 1,1-dimethylnitroethane; trimethylsilylazide / acetonitrile / 2 h / 20 °C / |Inert atmosphere; |Cooling 3: FeBr2 / toluene / 16 h / 140 °C / |Schlenk technique; |Inert atmosphere View Scheme

1: sodium hydrogencarbonate; ethanol 2: zinc chloride / 170 °C View Scheme