1: 10 percent / pyridine 2: 85 percent / Cs2CO3 / acetonitrile / Ambient temperature View Scheme

pyridine

1: 10 percent / pyridine 2: 85 percent / Cs2CO3 / acetonitrile / Ambient temperature 3: 60 percent / tetrabutylammonium fluoride 4: 83 percent 5: 1) thiocarbonyldiimidazole, 2) tributyltin hydride, α,α'-azobisisobutyronitrile / 1) toluene, acetonitrile, 2) toluene View Scheme

1: 10 percent / pyridine 2: 85 percent / Cs2CO3 / acetonitrile / Ambient temperature 3: 60 percent / tetrabutylammonium fluoride 4: 83 percent View Scheme

1: 53 percent / pyridine 2: 87 percent / Cs2CO3 / acetonitrile / Ambient temperature 3: 73 percent / tetrabutylammonium fluoride View Scheme

1: 4-dimethylaminopyridone / acetonitrile / 2 h / Ambient temperature 2: α,α'-azobisisobutyronitrile, tributyltin hydride / toluene / 4 h / 70 °C 3: 61 percent / tetrabutylammonium fluoride trihydrate / tetrahydrofuran / 1 h / Ambient temperature 4: 93 percent / pyridine / 24 h / 18 °C 5: pyridine / CH2Cl2 / 2 h / Ambient temperature 6: 60 percent / tributyltin hydride, α,α'-azobisisobutironitrile / toluene / 3 h / 70 °C 7: 1N NaOH / methanol / 5 h / Heating; pH = 9 View Scheme

1: 4-dimethylaminopyridone / acetonitrile / 2 h / Ambient temperature 2: α,α'-azobisisobutyronitrile, tributyltin hydride / toluene / 4 h / 70 °C 3: 61 percent / tetrabutylammonium fluoride trihydrate / tetrahydrofuran / 1 h / Ambient temperature 4: 93 percent / pyridine / 24 h / 18 °C 5: pyridine / CH2Cl2 / 2 h / Ambient temperature 6: 60 percent / tributyltin hydride, α,α'-azobisisobutironitrile / toluene / 3 h / 70 °C 7: 94 percent / 1N HCl / methanol / 0.5 h / Ambient temperature View Scheme