Oxidative Benzannulation of Indoles with 3-Alkynyl-4-pyrones for the Synthesis of Furo[2,3- b ]carbazoles

We report a mild and operationally simple strategy for the synthesis of furo[2,3-b]carbazoles via the oxidative benzannulation of 2,3-unsubstituted indoles with 3-alkynyl-4-pyrones. This domino transformation proceeds at room temperature in the presence of methanesulfonic acid as the sole promoter. The method allows for the construction of a broad scope of polysubstituted furo[2,3-b]carbazoles in up to 92% yield. The photophysical properties of the polycyclic products were determined to assess their potential as fluorophores.

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Journal
The Journal of Organic Chemistry
Published
2026-09-11
DOI
https://doi.org/10.1021/acs.joc.6c01620
Primary Topic
Catalytic C–H Functionalization Methods
Type
article
Field-Weighted Citation Impact
0.00

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article

Oxidative Benzannulation of Indoles with 3-Alkynyl-4-pyrones for the Synthesis of Furo[2,3- b ]carbazoles

Vladislav V. Fedin, Vyacheslav Ya. Sosnovskikh, Sergey А. Usachev, Дмитрий Л. Обыденнов et al.
The Journal of Organic Chemistry
Catalytic C–H Functionalization Methods
article

Oxidative Benzannulation of Indoles with 3-Alkynyl-4-pyrones for the Synthesis of Furo[2,3- b ]carbazoles

Vladislav V. Fedin, Vyacheslav Ya. Sosnovskikh, Sergey А. Usachev, Дмитрий Л. Обыденнов, Egor O. Sofin
article en

Abstract

We report a mild and operationally simple strategy for the synthesis of furo[2,3-b]carbazoles via the oxidative benzannulation of 2,3-unsubstituted indoles with 3-alkynyl-4-pyrones. This domino transformation proceeds at room temperature in the presence of methanesulfonic acid as the sole promoter. The method allows for the construction of a broad scope of polysubstituted furo[2,3-b]carbazoles in up to 92% yield. The photophysical properties of the polycyclic products were determined to assess their potential as fluorophores.

The Journal of Organic Chemistry
Ural Federal University (RU)
Russian Science Foundation
Openalex Percentile: Top 21%
Catalytic C–H Functionalization Methods
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