potassium hydroxide in ethanol 0.5 h; Heating;

1: 1.) K2CO3, 2.) Cu, CuI / 1.) DMF, 120 deg C, 10 min, 2.) DMF, reflux, 50 h 2: 1.) 50percent polyphosphoric acid, 2.) pyridine / 1.) 120 deg C, 3 h, 2.) reflux, 16 h 3: 87 percent / 56percent HI / 4 h / Heating 4: 92 percent / pyridine / 1.5 h / 50 °C 5: 46 percent / 5 N aq. acetic acid / 72 h / 70 °C 6: 88 percent / 5 N aq. KOH / ethanol / 0.5 h / Heating View Scheme

1: 1.) K2CO3, 2.) Cu, CuI / 1.) DMF, 120 deg C, 10 min, 2.) DMF, reflux, 50 h 2: 1.) 50percent polyphosphoric acid, 2.) pyridine / 1.) 120 deg C, 3 h, 2.) reflux, 16 h 3: 87 percent / 56percent HI / 4 h / Heating 4: 92 percent / pyridine / 1.5 h / 50 °C 5: 46 percent / 5 N aq. acetic acid / 72 h / 70 °C 6: 88 percent / 5 N aq. KOH / ethanol / 0.5 h / Heating View Scheme

1: 1.) 50percent polyphosphoric acid, 2.) pyridine / 1.) 120 deg C, 3 h, 2.) reflux, 16 h 2: 87 percent / 56percent HI / 4 h / Heating 3: 92 percent / pyridine / 1.5 h / 50 °C 4: 46 percent / 5 N aq. acetic acid / 72 h / 70 °C 5: 88 percent / 5 N aq. KOH / ethanol / 0.5 h / Heating View Scheme

1: 92 percent / pyridine / 1.5 h / 50 °C 2: 46 percent / 5 N aq. acetic acid / 72 h / 70 °C 3: 88 percent / 5 N aq. KOH / ethanol / 0.5 h / Heating View Scheme

1: 87 percent / 56percent HI / 4 h / Heating 2: 92 percent / pyridine / 1.5 h / 50 °C 3: 46 percent / 5 N aq. acetic acid / 72 h / 70 °C 4: 88 percent / 5 N aq. KOH / ethanol / 0.5 h / Heating View Scheme

1: 46 percent / 5 N aq. acetic acid / 72 h / 70 °C 2: 88 percent / 5 N aq. KOH / ethanol / 0.5 h / Heating View Scheme