1: 85 percent / DMAP / acetonitrile / 28 h / Ambient temperature 2: 90 percent / Bu3SnH, 2,2'-azobis(2-methylpropionitrile) / benzene / 0.33 h / Heating 3: 83 percent / aq. AcOH / 1 h / Ambient temperature 4: 1) hydrazine, 2) Raney Ni / 1) 90 min, reflux, 2) aq. EtOH, reflux, 2 h View Scheme

1: 90 percent / Bu3SnH, 2,2'-azobis(2-methylpropionitrile) / benzene / 0.33 h / Heating 2: 83 percent / aq. AcOH / 1 h / Ambient temperature 3: 1) hydrazine, 2) Raney Ni / 1) 90 min, reflux, 2) aq. EtOH, reflux, 2 h View Scheme

1: 82 percent / AgNO3, pyridine / tetrahydrofuran / 3.5 h / Ambient temperature 2: 85 percent / DMAP / acetonitrile / 28 h / Ambient temperature 3: 90 percent / Bu3SnH, 2,2'-azobis(2-methylpropionitrile) / benzene / 0.33 h / Heating 4: 83 percent / aq. AcOH / 1 h / Ambient temperature 5: 1) hydrazine, 2) Raney Ni / 1) 90 min, reflux, 2) aq. EtOH, reflux, 2 h View Scheme

1: 92 percent / methanolic NH3 / 16 h / Ambient temperature 2: 82 percent / AgNO3, pyridine / tetrahydrofuran / 3.5 h / Ambient temperature 3: 85 percent / DMAP / acetonitrile / 28 h / Ambient temperature 4: 90 percent / Bu3SnH, 2,2'-azobis(2-methylpropionitrile) / benzene / 0.33 h / Heating 5: 83 percent / aq. AcOH / 1 h / Ambient temperature 6: 1) hydrazine, 2) Raney Ni / 1) 90 min, reflux, 2) aq. EtOH, reflux, 2 h View Scheme

1: 61 percent / KOH, tris-<2-(2-methoxyethoxy)ethyl>amine / acetonitrile / 1 h / Ambient temperature 2: 92 percent / methanolic NH3 / 16 h / Ambient temperature 3: 82 percent / AgNO3, pyridine / tetrahydrofuran / 3.5 h / Ambient temperature 4: 85 percent / DMAP / acetonitrile / 28 h / Ambient temperature 5: 90 percent / Bu3SnH, 2,2'-azobis(2-methylpropionitrile) / benzene / 0.33 h / Heating 6: 83 percent / aq. AcOH / 1 h / Ambient temperature 7: 1) hydrazine, 2) Raney Ni / 1) 90 min, reflux, 2) aq. EtOH, reflux, 2 h View Scheme

1: 61 percent / KOH, tris-<2-(2-methoxyethoxy)ethyl>amine / acetonitrile / 1 h / Ambient temperature 2: 92 percent / methanolic NH3 / 16 h / Ambient temperature 3: 82 percent / AgNO3, pyridine / tetrahydrofuran / 3.5 h / Ambient temperature 4: 85 percent / DMAP / acetonitrile / 28 h / Ambient temperature 5: 90 percent / Bu3SnH, 2,2'-azobis(2-methylpropionitrile) / benzene / 0.33 h / Heating 6: 83 percent / aq. AcOH / 1 h / Ambient temperature 7: 1) hydrazine, 2) Raney Ni / 1) 90 min, reflux, 2) aq. EtOH, reflux, 2 h View Scheme

1: 1.) KOH, tris<2-(2-methoxyethoxy)ethyl>amine (TDA-1) / 1.) MeCN, r.t., 2.) THF, 10 min. 2: 93 percent / Bu4NF / tetrahydrofuran / 0.25 h / Ambient temperature 3: 1,) hydrazine hydrate, 2.) Raney-Ni / 1.) 120-130 deg C, 90 min., 2.) ethanol, 2 h, heating View Scheme

1: CCl4, tris(dimethylamino)phosphane / tetrahydrofuran / 4 h / -80 °C 2: 1.) KOH, tris<2-(2-methoxyethoxy)ethyl>amine (TDA-1) / 1.) MeCN, r.t., 2.) THF, 10 min. 3: 93 percent / Bu4NF / tetrahydrofuran / 0.25 h / Ambient temperature 4: 1,) hydrazine hydrate, 2.) Raney-Ni / 1.) 120-130 deg C, 90 min., 2.) ethanol, 2 h, heating View Scheme

1: 93 percent / Bu4NF / tetrahydrofuran / 0.25 h / Ambient temperature 2: 1,) hydrazine hydrate, 2.) Raney-Ni / 1.) 120-130 deg C, 90 min., 2.) ethanol, 2 h, heating View Scheme

nickel; hydrazine hydrate 1.) 120-130 deg C, 90 min., 2.) ethanol, 2 h, heating; Yield given. Multistep reaction;