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Synthesis of N-acyl carbazoles, phenoxazines and acridines from cyclic diaryliodonium salts.

ABSTRACT: N-Acyl carbazoles can be efficiently produced through a single-step process using amides and cyclic diaryliodonium triflates. This convenient reaction is facilitated by copper iodide in p-xylene, using the commonly found activating ligand diglyme. We have tested this method with a wide range of amides and iodonium triflates, proving its versatility with numerous substrates. Beyond carbazoles, we also produced a variety of other N-heterocycles, such as acridines, phenoxazines, or phenazines, showcasing the robustness of our technique. In a broader sense, this new method creates two C-N bonds simultaneously based on a mono-halogenated starting material, thus allowing heterocycle formation with diminished halogen waste.

SUBMITTER: Clamor N

PROVIDER: S-EPMC10777325 | biostudies-literature | 2024

REPOSITORIES: biostudies-literature

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Synthesis of N-acyl carbazoles, phenoxazines and acridines from cyclic diaryliodonium salts.

Clamor Nils N Damrath Mattis M Kuczmera Thomas J TJ Duvinage Daniel D Nachtsheim Boris J BJ

Beilstein journal of organic chemistry 20240104

N-Acyl carbazoles can be efficiently produced through a single-step process using amides and cyclic diaryliodonium triflates. This convenient reaction is facilitated by copper iodide in p-xylene, using the commonly found activating ligand diglyme. We have tested this method with a wide range of amides and iodonium triflates, proving its versatility with numerous substrates. Beyond carbazoles, we also produced a variety of other N-heterocycles, such as acridines, phenoxazines ...[more]

PMID: 38213840

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