ControllableMolecular Editing of 2‑Amino‑<i>N</i>‑substitutedBenzamides: Site-selective Synthesisof 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 AgNO<sub>3</sub> as the nitrogen synthon.

Publication Details

Journal
Figshare
Published
2025-02-03
DOI
https://doi.org/10.1021/acs.orglett.4c04783.s001
Primary Topic
Catalytic C–H Functionalization Methods
Type
article
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article

ControllableMolecular Editing of 2‑Amino‑N‑substitutedBenzamides: Site-selective Synthesisof 6‑Selenylated N‑Substituted 1,2,3-Benzotriazine-4(3H)‑ones

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Catalytic C–H Functionalization Methods
article

ControllableMolecular Editing of 2‑Amino‑N‑substitutedBenzamides: Site-selective Synthesisof 6‑Selenylated N‑Substituted 1,2,3-Benzotriazine-4(3H)‑ones

article en

Abstract

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 AgNO<sub>3</sub> as the nitrogen synthon.

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Catalytic C–H Functionalization Methods
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