trimethylstannyl azide in benzene-d6 T=115°C; 24 h;

1: LiCl, (i-Pr)2NEt / tetrahydrofuran / 15 h / Heating 2: NaOMe / methanol / a) RT, 20 h, b) reflux, 2 h 3: POCl3 / toluene / 8 h / Heating 4: NH2NH2*H2O / ethanol / 2 h / Heating 5: 91 percent / various solvent(s) / 6 h / 160 - 165 °C 6: 86 percent / Me3SnN3 / benzene-d6 / 24 h / 115 °C View Scheme

1: LiCl, (i-Pr)2NEt / tetrahydrofuran / 15 h / Heating 2: NaOMe / methanol / a) RT, 20 h, b) reflux, 2 h 3: POCl3 / toluene / 8 h / Heating 4: NH2NH2*H2O / ethanol / 2 h / Heating 5: 91 percent / various solvent(s) / 6 h / 160 - 165 °C 6: 86 percent / Me3SnN3 / benzene-d6 / 24 h / 115 °C View Scheme

1: NH2NH2*H2O / ethanol / 2 h / Heating 2: 91 percent / various solvent(s) / 6 h / 160 - 165 °C 3: 86 percent / Me3SnN3 / benzene-d6 / 24 h / 115 °C View Scheme

1: NaOMe / methanol / a) RT, 20 h, b) reflux, 2 h 2: POCl3 / toluene / 8 h / Heating 3: NH2NH2*H2O / ethanol / 2 h / Heating 4: 91 percent / various solvent(s) / 6 h / 160 - 165 °C 5: 86 percent / Me3SnN3 / benzene-d6 / 24 h / 115 °C View Scheme

1: 98 percent / POCl3 / 6 h / 100 °C 2: 92 percent / N2H4 / ethanol / 2 h / Heating 3: 94 percent / N-methylpyrrolidone / 6 h / 160 °C 4: 1.) Me3SnN3, 2.) HCl (gas) / 1.) xylene, 115 deg C, 48 h, 2.) THF, RT, 1 h View Scheme

1: 91 percent / various solvent(s) / 6 h / 160 - 165 °C 2: 86 percent / Me3SnN3 / benzene-d6 / 24 h / 115 °C View Scheme