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

We present an efficient silver-catalyzed one-pot controllable molecular editing protocol for the transformation of 2-amino-<i>N</i>-substituted benzamides into 6-selenylated <i>N</i>-substituted 1,2,3-benzotriazine-4(3<i>H</i>)-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(3<i>H</i>)-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-<i>N</i>-substituted benzamides with readily available diselenides, followed by annulation of selenylated 2-amino-<i>N</i>-substituted benzamides using AgNO₃ as the nitrogen synthon.