carbon disulfide; potassium hydroxide in ethanol; acetonitrile

1: 1.93 g / Na2CO3, KI / dimethylformamide / 16 h / Ambient temperature 2: 1.75 g / LAH / tetrahydrofuran / 8 h / Heating 3: 54 percent / tetrahydrofuran / 0.5 h / Heating View Scheme

in tetrahydrofuran

in isopropyl alcohol

1: oxaloyl chloride / toluene; dimethylformamide / 0.5 h / 70 °C 2: 84 percent / K2CO3 / H2O; toluene / 11 h / 0 °C 3: 58 percent / BH3*SMe2 / tetrahydrofuran / 12 h / Heating 4: 93 percent / K2CO3 / dimethylformamide / 4 h / 135 °C / other dihalo-3-nitrobenzyl diamines, regioselectivity 5: 65 percent / K2CO3 / dimethylformamide / 24 h / 23 °C 6: H2 / 5percent Pd/C / methanol / 0.33 h / 23 °C 7: methanol / 6.5 h View Scheme

in tetrahydrofuran 0.5 h; Heating;

1: 71 percent / sodium acetate, NaBH3CN / methanol / 0.75 h / Ambient temperature 2: 1.) BH3*THF, 2.) NaOAc / 1.) glyme, RT, 72 h, 2.) n-BuOH, reflux, 72 h 3: 1.93 g / Na2CO3, KI / dimethylformamide / 16 h / Ambient temperature 4: 1.75 g / LAH / tetrahydrofuran / 8 h / Heating 5: 54 percent / tetrahydrofuran / 0.5 h / Heating View Scheme

1: 1.) BH3*THF, 2.) NaOAc / 1.) glyme, RT, 72 h, 2.) n-BuOH, reflux, 72 h 2: 1.93 g / Na2CO3, KI / dimethylformamide / 16 h / Ambient temperature 3: 1.75 g / LAH / tetrahydrofuran / 8 h / Heating 4: 54 percent / tetrahydrofuran / 0.5 h / Heating View Scheme

1: 1.93 g / Na2CO3, KI / dimethylformamide / 16 h / Ambient temperature 2: 1.75 g / LAH / tetrahydrofuran / 8 h / Heating 3: 54 percent / tetrahydrofuran / 0.5 h / Heating View Scheme

in methanol 6.5 h; Yield given;