trichlorophosphate in toluene T=85°C; Bischler-Napieralski cyclization; 1 h;

1: 100 percent / 12 h / 20 °C 2: 86 percent / POCl3 / toluene / 1 h / 85 °C View Scheme

1: ammonium acetate / acetic acid / 5 h / Inert atmosphere; Reflux 2: lithium aluminium tetrahydride / tetrahydrofuran / 10 °C / Inert atmosphere; Reflux 3: 12 h / Inert atmosphere; Reflux 4: phosphorus pentachloride / chloroform; N,N-dimethyl-formamide / -78 - 20 °C / Inert atmosphere 5: sodium hydroxide / chloroform; water / Inert atmosphere View Scheme

1: lithium aluminium tetrahydride / tetrahydrofuran / 10 °C / Inert atmosphere; Reflux 2: 12 h / Inert atmosphere; Reflux 3: phosphorus pentachloride / chloroform; N,N-dimethyl-formamide / -78 - 20 °C / Inert atmosphere 4: sodium hydroxide / chloroform; water / Inert atmosphere View Scheme

1.1: sodium hydride / tetrahydrofuran; mineral oil / 10 - 20 °C / Inert atmosphere 1.2: 18 h / Reflux; Inert atmosphere 2.1: ammonium acetate / acetic acid / 5 h / Inert atmosphere; Reflux 3.1: lithium aluminium tetrahydride / tetrahydrofuran / 10 °C / Inert atmosphere; Reflux 4.1: 12 h / Inert atmosphere; Reflux 5.1: phosphorus pentachloride / chloroform; N,N-dimethyl-formamide / -78 - 20 °C / Inert atmosphere 6.1: sodium hydroxide / chloroform; water / Inert atmosphere View Scheme

1.1: sodium hydride / tetrahydrofuran; mineral oil / 10 - 20 °C / Inert atmosphere 1.2: 18 h / Reflux; Inert atmosphere 2.1: ammonium acetate / acetic acid / 5 h / Inert atmosphere; Reflux 3.1: lithium aluminium tetrahydride / tetrahydrofuran / 10 °C / Inert atmosphere; Reflux 4.1: 12 h / Inert atmosphere; Reflux 5.1: phosphorus pentachloride / chloroform; N,N-dimethyl-formamide / -78 - 20 °C / Inert atmosphere 6.1: sodium hydroxide / chloroform; water / Inert atmosphere View Scheme

1.1: LiAlH4 / diethyl ether / 30 h / Heating 1.2: 80 percent / NaOH / diethyl ether; H2O / 0.5 h / cooling 2.1: 100 percent / 12 h / 20 °C 3.1: 86 percent / POCl3 / toluene / 1 h / 85 °C View Scheme

toluene; trichlorophosphate

1: tetrahydrofuran / 2 h / 0 °C 2: 83 percent / LDA / tetrahydrofuran / 1.) -40 deg C, 3 h, 2.) 20 deg C, 12 h 3: 98 percent / 20percent aq. KOH / 48 h / Heating 4: 97 percent / conc. aq. HCl / 1 h / Heating 5: 86 percent / I2 / methanol / 4 h / Heating View Scheme

1: 2.) NaBH4 / 1.) MeCN, reflux, 2 h, 2.) MeOH, room temperature, 5 h 2: 74 percent / conc. HCl / ethanol / 3 h / Heating View Scheme