triethylamine in methanol; water Cyclization; deacetylation; Heating;

1: 45 percent / K2CO3 / dimethylsulfoxide / 360 h / 23 °C 2: NH3 / methanol / 5 h / 0 °C 3: 91 percent / Et3N / DMAP / acetonitrile / 1 h / 23 °C 4: 65 percent / (CF3CO)2O; pyridine / tetrahydrofuran / -12 - -2 °C 5: 72 percent / Et3N / H2O; methanol / Heating View Scheme

1: 95 percent / K2CO3 / dimethylsulfoxide / 15 h / 23 °C 2: 98 percent / NaOMe / methanol / 2 h / 23 °C 3: NH3 / methanol / 5 h / 0 °C 4: 91 percent / Et3N / DMAP / acetonitrile / 1 h / 23 °C 5: 65 percent / (CF3CO)2O; pyridine / tetrahydrofuran / -12 - -2 °C 6: 72 percent / Et3N / H2O; methanol / Heating View Scheme

1: 26.3 g / DMAP; pyridine / acetonitrile 2: (CF3CO)2O; pyridine / tetrahydrofuran / -10 °C 3: NEt3 / methanol View Scheme

ammonia T=100°C; 15 h; in a steel bomb;

1: 45 percent / K2CO3 / dimethylsulfoxide / 360 h / 23 °C 2: NH3 / methanol / 5 h / 0 °C 3: 91 percent / Et3N / DMAP / acetonitrile / 1 h / 23 °C 4: 65 percent / (CF3CO)2O; pyridine / tetrahydrofuran / -12 - -2 °C 5: 72 percent / Et3N / H2O; methanol / Heating View Scheme

1: NH3 / methanol / 5 h / 0 °C 2: 91 percent / Et3N / DMAP / acetonitrile / 1 h / 23 °C 3: 65 percent / (CF3CO)2O; pyridine / tetrahydrofuran / -12 - -2 °C 4: 72 percent / Et3N / H2O; methanol / Heating View Scheme

1: 98 percent / NaOMe / methanol / 2 h / 23 °C 2: NH3 / methanol / 5 h / 0 °C 3: 91 percent / Et3N / DMAP / acetonitrile / 1 h / 23 °C 4: 65 percent / (CF3CO)2O; pyridine / tetrahydrofuran / -12 - -2 °C 5: 72 percent / Et3N / H2O; methanol / Heating View Scheme

1: 90 percent / p-toluenesulfonyl azide, 1,5-diazabicyclo<5.4.0>undec-5-ene / ethyl acetate / 1 h / Ambient temperature 2: 82.3 percent / hydrogen / platinum oxide / acetic acid; 2-methoxy-ethanol / 4 h / 1810.02 Torr / Ambient temperature 3: 54.3 percent / conc. ammonium hydroxide / 8 h / Ambient temperature 4: 78.3 percent / phosphoryl chloride / 1.5 h / Heating 5: 1.) hexamethyldisilazane, ammonium sulfate; 2.) stannic chloride / 1.) reflux, 15 h; 2.) 1,2-dichloroethane, 20 h, r.t. 6: 37 percent / liquid ammonia / 15 h / 100 °C / in a steel bomb View Scheme

1: 82.3 percent / hydrogen / platinum oxide / acetic acid; 2-methoxy-ethanol / 4 h / 1810.02 Torr / Ambient temperature 2: 54.3 percent / conc. ammonium hydroxide / 8 h / Ambient temperature 3: 78.3 percent / phosphoryl chloride / 1.5 h / Heating 4: 1.) hexamethyldisilazane, ammonium sulfate; 2.) stannic chloride / 1.) reflux, 15 h; 2.) 1,2-dichloroethane, 20 h, r.t. 5: 37 percent / liquid ammonia / 15 h / 100 °C / in a steel bomb View Scheme