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

Organic Letters, Год журнала: 2025, Номер unknown

Опубликована: Фев. 3, 2025

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 strategy is achieved by building N-N/N═N/C-Se bonds, which provides a practical pathway preparation selenylated with broad substrate scope and good functional group tolerance, as well high site-selectivity. Mechanistic experiments suggest that this proceeds via intermolecular site-selective C-H selenylation readily available diselenides, followed annulation using AgNO3 nitrogen synthon.

Язык: Английский

Cu(II)‐Catalyzed Annulation of o‐Phenylenediamines and Phenacyl Bromides for the Facile Synthesis of 2‐Functionalized Quinoxalines

ChemistrySelect, Год журнала: 2025, Номер 10(18)

Опубликована: Май 1, 2025

Abstract A facile Cu(II)‐catalyzed annulation of o ‐phenylenediamine and phenacyl bromides in EtOH has been developed. In this protocol, diverse 2‐functionalized quinoxalines were prepared 74%–91% yields with high chemoselectivity. The salient features are the excellent yields, broad substrate scope, mild reaction conditions, large‐scale preparation. This not only fills gap conventional metal‐catalyzed o‐phenylenediamine but also provides a practical strategy for construction quinoxalines.

Язык: Английский

Base-Controlled Chemodivergent [4 + 1] and [2 + 1]/[4 + 2] Annulations of o-Aminochalcones with γ-Bromocrotonates

Organic Letters, Год журнала: 2024, Номер 26(43), С. 9203 - 9209

Опубликована: Окт. 21, 2024

Controlling the selectivity of reactions is a significantly attractive strategy in synthetic organic chemistry. Herein, an efficient base-controlled chemodivergent domino reaction between o-aminochalcones and γ-bromocrotonates has been developed. A series cis-2,3-disubstituted indolines cyclopropane-fused tetrahydroquinolines were obtained via two pathways with broad substrate scope moderate to excellent yields under transition-metal-free conditions. It noteworthy that could be used as C1 or C2 synthons by modulating base; particular, both nucleophiles electrophiles generate cyclopropanes for first time.

Язык: Английский