1: 18.5 g / K2CO3, KI, Cu bronze / dimethylformamide / 18 h / Heating 2: 200 mg / conc. H2SO4 / 1.5 h / Heating 3: pyridine / 20 h / Heating 4: 48percent HI / 20 h / Heating View Scheme

1: 18.5 g / K2CO3, KI, Cu bronze / dimethylformamide / 18 h / Heating 2: 200 mg / conc. H2SO4 / 1.5 h / Heating 3: pyridine / 20 h / Heating 4: 48percent HI / 20 h / Heating View Scheme

1: 77 percent / Cu, K2CO3 / dimethylformamide / 18 h / Heating 2: 1.) 50percent polyphosphoric acid / 1.) 130 deg C, 4 h, 2.) reflux, 18 h 3: 44.5 percent / 5 N aq. acetic acid / 4 h / Heating 4: 64 percent / MnO2 / diethyl ether / 2 h / Heating 5: 13 percent / pyridine hydrochloride / 3.5 h / 140 °C 6: 54 percent / NaBH4 / methanol / 1 h / Ambient temperature View Scheme

1: 77 percent / Cu, K2CO3 / dimethylformamide / 18 h / Heating 2: 1.) 50percent polyphosphoric acid / 1.) 130 deg C, 4 h, 2.) reflux, 18 h 3: 35 percent / 5 N aq. acetic acid / 4 h / Heating 4: 50 percent / MnO2 / diethyl ether / 2 h / Heating 5: 83 percent / pyridine hydrochloride / 1.5 h / 185 °C 6: 77 percent / NaBH4 / methanol / 1 h / Ambient temperature View Scheme

copper; potassium carbonate in N,N-dimethyl-formamide 18 h; Heating;

1: 77 percent / Cu, K2CO3 / dimethylformamide / 18 h / Heating 2: 50percent polyphosphoric acid / 4 h / 130 °C View Scheme

1: 77 percent / Cu, K2CO3 / dimethylformamide / 18 h / Heating 2: 1.) 50percent polyphosphoric acid / 1.) 130 deg C, 4 h, 2.) reflux, 18 h 3: 71 percent / 56percent HI / 3 h / Heating View Scheme

1: 77 percent / Cu, K2CO3 / dimethylformamide / 18 h / Heating 2: 1.) 50percent polyphosphoric acid / 1.) 130 deg C, 4 h, 2.) reflux, 18 h 3: 71 percent / 56percent HI / 3 h / Heating 4: 86 percent / pyridine / 1 h / Ambient temperature View Scheme