Controllable Molecular Editing of 2-Amino-N-substituted Benzamides: Site-selective Synthesis of 6-Selenylated N-Substituted 1,2,3-Benzotriazine-4(3H)-ones

We present an efficient silver-catalyzed one-pot controllable molecular editing protocol for the transformation of 2-amino-N-substituted benzamides into 6-selenylated N-substituted 1,2,3-benzotriazine-4(3H)-ones under mild reaction conditions. This three-component reaction strategy is achieved by building N-N/N═N/C-Se bonds, which provides a practical pathway for the preparation of selenylated 1,2,3-benzotriazine-4(3H)-ones with a broad substrate scope and good functional group tolerance, as well as high site-selectivity. Mechanistic experiments suggest that this reaction proceeds via intermolecular site-selective C-H selenylation of 2-amino-N-substituted benzamides with readily available diselenides, followed by annulation of selenylated 2-amino-N-substituted benzamides using AgNO3 as the nitrogen synthon.