1: 50.8 g / toluene-4-sulphonic acid / 16 h / 0 °C 2: 1.) Li 3: 91 percent / BBr3 / CH2Cl2 / 1.) -80 deg C, 3 d, 2.) 72 h 4: 1.) LiNH2, Fe(NO3)3 / 1.) liq. NH3, THF, HMPA, 2.) liq. NH3, THF, HMPA, 40 deg C, 24 h 5: p-TsOH / ethanol / 3 h / Heating 6: 0.1704 g / PBr3 / CHCl3 / 16 h / -30 deg C to r. t. 7: 1.) EtMgBr, CuCl / 1.) THF, 1 h, 2.) THF, 72 h, 35 deg C 8: 50 percent / H2, quinoline / 5 percent Pd-BaSO4 / ethyl acetate / 2 h / Ambient temperature View Scheme

1: 39 percent / conc. HCl, CuCl / toluene / 24 h / 100 °C 2: 50.8 g / toluene-4-sulphonic acid / 16 h / 0 °C 3: 1.) Li 4: 91 percent / BBr3 / CH2Cl2 / 1.) -80 deg C, 3 d, 2.) 72 h 5: 1.) LiNH2, Fe(NO3)3 / 1.) liq. NH3, THF, HMPA, 2.) liq. NH3, THF, HMPA, 40 deg C, 24 h 6: p-TsOH / ethanol / 3 h / Heating 7: 0.1704 g / PBr3 / CHCl3 / 16 h / -30 deg C to r. t. 8: 1.) EtMgBr, CuCl / 1.) THF, 1 h, 2.) THF, 72 h, 35 deg C 9: 50 percent / H2, quinoline / 5 percent Pd-BaSO4 / ethyl acetate / 2 h / Ambient temperature View Scheme

1: 1.) Mg / 1.) THF, 2.) THF, 24 h 2: 81 percent / toluene-4-sulphonic acid / ethanol / 24 h / Heating 3: 1.) KOH, 2.) H2, H2SO4 / 2.) 10percent Pd/C / 1.) ethanol, 1 h, reflux, 2.) ethanol, r.t. 4: 4.31 g / PBr3 / CHCl3 / 4 h / 0 °C 5: 1.) LiNH2, Fe(NO3)3 / 1.) liq. NH3, THF, HMPA, 2.) liq. NH3, THF, HMPA, 40 deg C, 24 h 6: p-TsOH / ethanol / 3 h / Heating 7: 0.1704 g / PBr3 / CHCl3 / 16 h / -30 deg C to r. t. 8: 1.) EtMgBr, CuCl / 1.) THF, 1 h, 2.) THF, 72 h, 35 deg C 9: 50 percent / H2, quinoline / 5 percent Pd-BaSO4 / ethyl acetate / 2 h / Ambient temperature View Scheme

1: 91 percent / BBr3 / CH2Cl2 / 1.) -80 deg C, 3 d, 2.) 72 h 2: 1.) LiNH2, Fe(NO3)3 / 1.) liq. NH3, THF, HMPA, 2.) liq. NH3, THF, HMPA, 40 deg C, 24 h 3: p-TsOH / ethanol / 3 h / Heating 4: 0.1704 g / PBr3 / CHCl3 / 16 h / -30 deg C to r. t. 5: 1.) EtMgBr, CuCl / 1.) THF, 1 h, 2.) THF, 72 h, 35 deg C 6: 50 percent / H2, quinoline / 5 percent Pd-BaSO4 / ethyl acetate / 2 h / Ambient temperature View Scheme

1: 2.) H2 2: 91 percent / BBr3 / CH2Cl2 / 1.) -80 deg C, 3 d, 2.) 72 h 3: 1.) LiNH2, Fe(NO3)3 / 1.) liq. NH3, THF, HMPA, 2.) liq. NH3, THF, HMPA, 40 deg C, 24 h 4: p-TsOH / ethanol / 3 h / Heating 5: 0.1704 g / PBr3 / CHCl3 / 16 h / -30 deg C to r. t. 6: 1.) EtMgBr, CuCl / 1.) THF, 1 h, 2.) THF, 72 h, 35 deg C 7: 50 percent / H2, quinoline / 5 percent Pd-BaSO4 / ethyl acetate / 2 h / Ambient temperature View Scheme

1: 1.) LiNH2, Fe(NO3)3 / 1.) liq. NH3, THF, HMPA, 2.) liq. NH3, THF, HMPA, 40 deg C, 24 h 2: p-TsOH / ethanol / 3 h / Heating 3: 0.1704 g / PBr3 / CHCl3 / 16 h / -30 deg C to r. t. 4: 1.) EtMgBr, CuCl / 1.) THF, 1 h, 2.) THF, 72 h, 35 deg C 5: 50 percent / H2, quinoline / 5 percent Pd-BaSO4 / ethyl acetate / 2 h / Ambient temperature View Scheme

1: 1.) NH2NH2*H2O, 2.) KO-t-Bu / 1.) ethanol, 7 h, heating, 2.) DMSO, 24 h, 80 deg C 2: 91 percent / BBr3 / CH2Cl2 / 1.) -80 deg C, 3 d, 2.) 72 h 3: 1.) LiNH2, Fe(NO3)3 / 1.) liq. NH3, THF, HMPA, 2.) liq. NH3, THF, HMPA, 40 deg C, 24 h 4: p-TsOH / ethanol / 3 h / Heating 5: 0.1704 g / PBr3 / CHCl3 / 16 h / -30 deg C to r. t. 6: 1.) EtMgBr, CuCl / 1.) THF, 1 h, 2.) THF, 72 h, 35 deg C 7: 50 percent / H2, quinoline / 5 percent Pd-BaSO4 / ethyl acetate / 2 h / Ambient temperature View Scheme

1: K2CO3 / xylene / 24 h / 145 °C 2: 1.) Mg / 1.) THF, 2.) THF, 24 h 3: 81 percent / toluene-4-sulphonic acid / ethanol / 24 h / Heating 4: 1.) KOH, 2.) H2, H2SO4 / 2.) 10percent Pd/C / 1.) ethanol, 1 h, reflux, 2.) ethanol, r.t. 5: 4.31 g / PBr3 / CHCl3 / 4 h / 0 °C 6: 1.) LiNH2, Fe(NO3)3 / 1.) liq. NH3, THF, HMPA, 2.) liq. NH3, THF, HMPA, 40 deg C, 24 h 7: p-TsOH / ethanol / 3 h / Heating 8: 0.1704 g / PBr3 / CHCl3 / 16 h / -30 deg C to r. t. 9: 1.) EtMgBr, CuCl / 1.) THF, 1 h, 2.) THF, 72 h, 35 deg C 10: 50 percent / H2, quinoline / 5 percent Pd-BaSO4 / ethyl acetate / 2 h / Ambient temperature View Scheme

1: 1.) LiH, 2.) Li / 1.) THF, 4 h, 2.) THF, 17 h 2: 1.) NH2NH2*H2O, 2.) KO-t-Bu / 1.) ethanol, 7 h, heating, 2.) DMSO, 24 h, 80 deg C 3: 91 percent / BBr3 / CH2Cl2 / 1.) -80 deg C, 3 d, 2.) 72 h 4: 1.) LiNH2, Fe(NO3)3 / 1.) liq. NH3, THF, HMPA, 2.) liq. NH3, THF, HMPA, 40 deg C, 24 h 5: p-TsOH / ethanol / 3 h / Heating 6: 0.1704 g / PBr3 / CHCl3 / 16 h / -30 deg C to r. t. 7: 1.) EtMgBr, CuCl / 1.) THF, 1 h, 2.) THF, 72 h, 35 deg C 8: 50 percent / H2, quinoline / 5 percent Pd-BaSO4 / ethyl acetate / 2 h / Ambient temperature View Scheme

1: 1.) Li 2: 91 percent / BBr3 / CH2Cl2 / 1.) -80 deg C, 3 d, 2.) 72 h 3: 1.) LiNH2, Fe(NO3)3 / 1.) liq. NH3, THF, HMPA, 2.) liq. NH3, THF, HMPA, 40 deg C, 24 h 4: p-TsOH / ethanol / 3 h / Heating 5: 0.1704 g / PBr3 / CHCl3 / 16 h / -30 deg C to r. t. 6: 1.) EtMgBr, CuCl / 1.) THF, 1 h, 2.) THF, 72 h, 35 deg C 7: 50 percent / H2, quinoline / 5 percent Pd-BaSO4 / ethyl acetate / 2 h / Ambient temperature View Scheme