Potassium Iodide/tert-Butyl Hydroperoxide-Mediated Oxidative Annulation for the Selective Synthesis of N-Substituted 1,2,3-Benzotriazine-4(3H)-ones Using Nitromethane as the Nitrogen Synthon

摘要

A novel and efficient oxidative annulation of 2-aminobenzamides with nitromethane has been developed for the chemoselective synthesis of N-substituted 1,2,3-benzotriazine-4(3H)-ones in moderate to excellent yields under transition metal-free conditions. Two N-N bonds were constructed in one pot via C-N cleavage of nitromethane, which was selectively employed as the nitrogen synthon. The preliminary mechanistic studies revealed that this protocol proceeded under hypoiodite catalysis generated in situ.