sodium hydroxide; N-benzyl-N,N,N-triethylammonium chloride in methanol T=45°C; 1.5 h;

selenium(IV) oxide in acetic acid T=100°C; 1 h;

1: 1.) sodium amide / 1.) toluene, 0 deg C, 10 min, 2.) toluene, 20 deg C, 5 h 2: 95 percent / ammonium formate / 10percent Pd/C / methanol / 48 °C 3: 94 percent / 30percent aq. NaOH, triethylbenzylammonium chloride / methanol / 1.5 h / 45 °C View Scheme

1: 95 percent / ammonium formate / 10percent Pd/C / methanol / 48 °C 2: 94 percent / 30percent aq. NaOH, triethylbenzylammonium chloride / methanol / 1.5 h / 45 °C View Scheme

T=160°C; P=0.08 Torr; 6 h;

in tetrahydrofuran; diethyl ether 2 h; Ambient temperature;

1: 40 percent / hydrazine hydrochloride, sodium pyrophosphate / propan-1-ol / 10 h / Heating; pH=6.5 2: 85 percent / selenium dioxide / acetic acid / 1 h / 100 °C View Scheme