Heterogeneously Catalyzed Cascade Oxidative Coupling/Dearomative Spirocyclization of Diarylamines: Facile Access to Spiroacridines

Abstract Spirocyclic compounds, particularly spirocyclohexadienones, are important in pharmaceuticals due to their biological activity. In this study, we develop a catalytic cascade oxidative spirocyclization of diarylamines for the rapid access to highly functionalized spirocyclohexadienones. Using commercially available recyclable heterogeneous metal catalysts, cascade process via oxidative coupling and dearomative spiroannulation proceeds efficiently under mild aerobic conditions, providing spirocyclohexadienones fused with an acridine skeleton in good‐to‐excellent yields. This method provides efficient and rapid access to nitrogen‐containing fused spiro compounds in a highly atom‐economical and environmentally friendly manner.

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Publication Details

Journal
Advanced Synthesis & Catalysis
Published
2025-03-12
DOI
https://doi.org/10.1002/adsc.202500107
Primary Topic
Catalytic C–H Functionalization Methods
Type
article
Field-Weighted Citation Impact
0.00

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article

Heterogeneously Catalyzed Cascade Oxidative Coupling/Dearomative Spirocyclization of Diarylamines: Facile Access to Spiroacridines

Tsukasa Hirokane, Naho Sato, Masahiro Yoshida, Yasuko Okamoto et al.
Advanced Synthesis & Catalysis
Catalytic C–H Functionalization Methods
article

Heterogeneously Catalyzed Cascade Oxidative Coupling/Dearomative Spirocyclization of Diarylamines: Facile Access to Spiroacridines

Tsukasa Hirokane, Naho Sato, Masahiro Yoshida, Yasuko Okamoto, Touya Kariya, Yoshinori Kobayashi, Kenichi Date, Kenji Matsumoto
article en

Abstract

Abstract Spirocyclic compounds, particularly spirocyclohexadienones, are important in pharmaceuticals due to their biological activity. In this study, we develop a catalytic cascade oxidative spirocyclization of diarylamines for the rapid access to highly functionalized spirocyclohexadienones. Using commercially available recyclable heterogeneous metal catalysts, cascade process via oxidative coupling and dearomative spiroannulation proceeds efficiently under mild aerobic conditions, providing spirocyclohexadienones fused with an acridine skeleton in good‐to‐excellent yields. This method provides efficient and rapid access to nitrogen‐containing fused spiro compounds in a highly atom‐economical and environmentally friendly manner.

Advanced Synthesis & CatalysisVol. 367(9)
Kagoshima University (JP), Tokushima Bunri University (JP)
Sankei Science Scholarship Foundation, Ministry of Education, Culture, Sports, Science and Technology, Iwatani Naoji Foundation
Openalex Percentile: Top 97%
Catalytic C–H Functionalization Methods
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