hydrazine hydrate in ethanol T=80°C; 8 h;

in ethyl acetate

1: 4-(2,2-diphenylvinyl)quinoline With potassium permanganate in tetrahydrofuran; water T=0°C; 5 h; 2: methanol With chloro-trimethyl-silane T=55°C; 72 h;

hydrogenchloride T=20°C;

1.1: PPh3; DEAD / tetrahydrofuran / 20 °C 2.1: BuLi / tetrahydrofuran / 0 °C 3.1: imidazole / dimethylformamide / 20 °C 4.1: 68 percent / BF3*OEt2 / CH2Cl2 / 1 h / 0 °C 5.1: 99 percent / p-TsOH*H2O / ethanol / 24 h / 78 °C 6.1: 94 percent / KOH / methanol / 30 h / 64 °C 7.1: KMnO4 / tetrahydrofuran; H2O / 5 h / 0 °C 7.2: 60 percent / Me3SiCl / 72 h / 55 °C View Scheme

1.1: BuLi / tetrahydrofuran / 0 °C 2.1: imidazole / dimethylformamide / 20 °C 3.1: 68 percent / BF3*OEt2 / CH2Cl2 / 1 h / 0 °C 4.1: 99 percent / p-TsOH*H2O / ethanol / 24 h / 78 °C 5.1: 94 percent / KOH / methanol / 30 h / 64 °C 6.1: KMnO4 / tetrahydrofuran; H2O / 5 h / 0 °C 6.2: 60 percent / Me3SiCl / 72 h / 55 °C View Scheme

1.1: 94 percent / KOH / methanol / 30 h / 64 °C 2.1: KMnO4 / tetrahydrofuran; H2O / 5 h / 0 °C 2.2: 60 percent / Me3SiCl / 72 h / 55 °C View Scheme

1.1: 99 percent / p-TsOH*H2O / ethanol / 24 h / 78 °C 2.1: 94 percent / KOH / methanol / 30 h / 64 °C 3.1: KMnO4 / tetrahydrofuran; H2O / 5 h / 0 °C 3.2: 60 percent / Me3SiCl / 72 h / 55 °C View Scheme

ethanol

benzeneseleninic anhydride 1.) dichlorobenzene, 130 deg C, 22 h, 2.) ether; Yield given. Multistep reaction;