in pyridine T=50°C; 3 h;

1: 1) lithium, ferric nitrate / 1) NH3(l)/THF, 1 h, 2) THF, 4 h 2: 80 percent / LiAlH4 / tetrahydrofuran / 1) rt, overnight, 2) reflux, 8 h 3: 78 percent / PBr3, pyridine / diethyl ether / 1) rt, 2 h, 2) reflux, 2.5 h 4: 1) magnesium / 3) Li2CuCl4 / 1) THF, a) rt, b) 30 deg C, 3 h, 2) THF, - 5 deg C, 30 min, 3) a) -5 to -10 deg C, 4 h, b) overnight 5: 67 percent / p-toluenesulphonic acid / methanol / 2 h / Heating 6: 70 percent / pyridine / neat (no solvent) / 24 h / Ambient temperature View Scheme

pyridine in tetrahydrofuran 1) -20 deg C, 0.5 h, 2) r.t., 3 h;

1: 82 percent / 1.) n-BuLi, 2.) HMPTA / 1.) benzene-THF, 20 deg C, 2 h, 2.) 20 deg C, 12 h 2: 98 percent / H2 / Lindlar catalyst / quinoline / 15 °C 3: 2.4 g / 1.) i-Bu2LiH, 2.) air, 3.) O2 / 1.) toluene, reflux, 7 h, 2.) 20 deg C, 3.) 60 - 65 deg C, 3 h; other reagent 4: 97 percent / pyridine / 3 h / 50 °C View Scheme

1: 98 percent / H2 / Lindlar catalyst / quinoline / 15 °C 2: 2.4 g / 1.) i-Bu2LiH, 2.) air, 3.) O2 / 1.) toluene, reflux, 7 h, 2.) 20 deg C, 3.) 60 - 65 deg C, 3 h; other reagent 3: 97 percent / pyridine / 3 h / 50 °C View Scheme

1: 1) magnesium / 3) Li2CuCl4 / 1) THF, a) rt, b) 30 deg C, 3 h, 2) THF, - 5 deg C, 30 min, 3) a) -5 to -10 deg C, 4 h, b) overnight 2: 67 percent / p-toluenesulphonic acid / methanol / 2 h / Heating 3: 70 percent / pyridine / neat (no solvent) / 24 h / Ambient temperature View Scheme

1: 80 percent / LiAlH4 / tetrahydrofuran / 1) rt, overnight, 2) reflux, 8 h 2: 78 percent / PBr3, pyridine / diethyl ether / 1) rt, 2 h, 2) reflux, 2.5 h 3: 1) magnesium / 3) Li2CuCl4 / 1) THF, a) rt, b) 30 deg C, 3 h, 2) THF, - 5 deg C, 30 min, 3) a) -5 to -10 deg C, 4 h, b) overnight 4: 67 percent / p-toluenesulphonic acid / methanol / 2 h / Heating 5: 70 percent / pyridine / neat (no solvent) / 24 h / Ambient temperature View Scheme

1: 78 percent / PBr3, pyridine / diethyl ether / 1) rt, 2 h, 2) reflux, 2.5 h 2: 1) magnesium / 3) Li2CuCl4 / 1) THF, a) rt, b) 30 deg C, 3 h, 2) THF, - 5 deg C, 30 min, 3) a) -5 to -10 deg C, 4 h, b) overnight 3: 67 percent / p-toluenesulphonic acid / methanol / 2 h / Heating 4: 70 percent / pyridine / neat (no solvent) / 24 h / Ambient temperature View Scheme

1: 1) LiNH2 / 1) liq. NH3, THF, 2 h; 2) THF, 3 h 2: 60 percent / LiAlH4 / diethyl ether / 1) 1 h; 2) 5 h, reflux 3: 70 percent / PBr3, pyridine / diethyl ether / 1) overnight, 2) reflux, 2 h 4: 1) Mg / 2)Li2CuCl4 / 1) THF, 2) THF, -10 deg C, 5 h 5: 70 percent / AcOH, pyridine / 12 h / Ambient temperature View Scheme

pyridine; acetic acid 12 h; Ambient temperature;