pyridine in chloroform T=60°C; 14 h;

1: 1.) polyphosphoric acid, 2.) potassium carbonate / 1.) dioxane, 60 deg C, 3 h, 2.) acetone, reflux, 50 h 2: 64 percent / potassium carbonate / acetone / 2 h / Heating 3: 93 percent / potassium carbonate / acetone / 4 h / Heating 4: 70 percent / NaBH4, PdCl2 / tetrahydrofuran; H2O / 1.5 h / 0 - 5 °C 5: 92 percent / toluene-p-sulfonic acid / toluene / 0.33 h / Heating 6: 95 percent / potassium carbonate / methanol / 1.5 h / Heating 7: 80 percent / sodium hydride / 0.5 h / 45 °C 8: 79 percent / pyridine / CHCl3 / 14 h / 60 °C View Scheme

1: 1.) polyphosphoric acid, 2.) potassium carbonate / 1.) dioxane, 60 deg C, 3 h, 2.) acetone, reflux, 50 h 2: 64 percent / potassium carbonate / acetone / 2 h / Heating 3: 93 percent / potassium carbonate / acetone / 4 h / Heating 4: 70 percent / NaBH4, PdCl2 / tetrahydrofuran; H2O / 1.5 h / 0 - 5 °C 5: 92 percent / toluene-p-sulfonic acid / toluene / 0.33 h / Heating 6: 95 percent / potassium carbonate / methanol / 1.5 h / Heating 7: 80 percent / sodium hydride / 0.5 h / 45 °C 8: 79 percent / pyridine / CHCl3 / 14 h / 60 °C View Scheme

1: 80 percent / sodium hydride / 0.5 h / 45 °C 2: 79 percent / pyridine / CHCl3 / 14 h / 60 °C View Scheme

1: 64 percent / potassium carbonate / acetone / 2 h / Heating 2: 93 percent / potassium carbonate / acetone / 4 h / Heating 3: 70 percent / NaBH4, PdCl2 / tetrahydrofuran; H2O / 1.5 h / 0 - 5 °C 4: 92 percent / toluene-p-sulfonic acid / toluene / 0.33 h / Heating 5: 95 percent / potassium carbonate / methanol / 1.5 h / Heating 6: 80 percent / sodium hydride / 0.5 h / 45 °C 7: 79 percent / pyridine / CHCl3 / 14 h / 60 °C View Scheme

1: 93 percent / potassium carbonate / acetone / 4 h / Heating 2: 70 percent / NaBH4, PdCl2 / tetrahydrofuran; H2O / 1.5 h / 0 - 5 °C 3: 92 percent / toluene-p-sulfonic acid / toluene / 0.33 h / Heating 4: 95 percent / potassium carbonate / methanol / 1.5 h / Heating 5: 80 percent / sodium hydride / 0.5 h / 45 °C 6: 79 percent / pyridine / CHCl3 / 14 h / 60 °C View Scheme

1: 70 percent / NaBH4, PdCl2 / tetrahydrofuran; H2O / 1.5 h / 0 - 5 °C 2: 92 percent / toluene-p-sulfonic acid / toluene / 0.33 h / Heating 3: 95 percent / potassium carbonate / methanol / 1.5 h / Heating 4: 80 percent / sodium hydride / 0.5 h / 45 °C 5: 79 percent / pyridine / CHCl3 / 14 h / 60 °C View Scheme

1: 92 percent / toluene-p-sulfonic acid / toluene / 0.33 h / Heating 2: 95 percent / potassium carbonate / methanol / 1.5 h / Heating 3: 80 percent / sodium hydride / 0.5 h / 45 °C 4: 79 percent / pyridine / CHCl3 / 14 h / 60 °C View Scheme

1: 95 percent / potassium carbonate / methanol / 1.5 h / Heating 2: 80 percent / sodium hydride / 0.5 h / 45 °C 3: 79 percent / pyridine / CHCl3 / 14 h / 60 °C View Scheme

1: 1.1 g / iodine, periodic acid / ethanol; H2O / 2 h / 60 - 70 °C 2: 1.) potassium carbonate, 2.) sodium hydroxide / 1.) acetone, reflux, 4 h, 2.) water 3: 0.7 g / sodium hydrogencarbonate / acetone / 6 h / Heating 4: potassium carbonate, potassium iodide / acetone / 30 h / Heating 5: 0.40 g / NN-dimethylaniline / 6 h / Heating View Scheme