1: 1.) aq. H2SO4, NaNO2, 2.) NaN3 / dioxane / 1.) 0-5 deg C, 20 min, 2.) RT, 70 min 2: 71 percent / aq. hydrazine / methanol / 1 h / Ambient temperature 3: 12 percent / methanol / 0.75 h / Ambient temperature; Irradiation View Scheme

1: 1.) aq. H2SO4, NaNO2, 2.) NaN3 / dioxane / 1.) 0-5 deg C, 20 min, 2.) RT, 70 min 2: 71 percent / aq. hydrazine / methanol / 1 h / Ambient temperature 3: 18 percent / methanol / 0.75 h / Ambient temperature; Irradiation View Scheme

1: 1.) aq. H2SO4, NaNO2, 2.) NaN3 / dioxane / 1.) 0-5 deg C, 20 min, 2.) RT, 70 min 2: 71 percent / aq. hydrazine / methanol / 1 h / Ambient temperature 3: 23 percent / methanol / 0.75 h / Ambient temperature; Irradiation View Scheme

1: 1.) NaNO2, aq. HCl, 2.) NaN3 / 1.) 0 deg C, 45 min, 2.) H2O, room temp., 5 h 2: 98 percent / N2H4*H2O / tetrahydrofuran; ethanol / Ambient temperature View Scheme