Rhodium-Catalyzed [4 + 2] Cascade Annulation to Easy Access N‑Substituted Indenoisoquinolinones

An efficient approach for the synthesis of N-substituted indenoisoquinolinones via rhodium­(III)-catalyzed C–H bond activation/subsequent [4 + 2] cyclization starting from easily available 2-phenyloxazolines and 2-diazo-1,3-indandiones has been developed. A series of indeno­[1,2-c]­isoquinolinones w...

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Bibliographic Details
Published in:Organic letters 2023-04, Vol.25 (16), p.2923-2927
Main Authors: Yue, Xuelin, Gao, Yijie, Huang, Junwei, Feng, Yadong, Cui, Xiuling
Format: Article
Language:English
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Summary:An efficient approach for the synthesis of N-substituted indenoisoquinolinones via rhodium­(III)-catalyzed C–H bond activation/subsequent [4 + 2] cyclization starting from easily available 2-phenyloxazolines and 2-diazo-1,3-indandiones has been developed. A series of indeno­[1,2-c]­isoquinolinones were obtained in up to 93% yield through C–H functionalization, followed by intramolecular annulation, elimination, and ring-opening in a “one pot manner” under mild reaction conditions. This protocol features excellent atom- and step-economy and provides a novel strategy for the synthesis of N-substituted indenoisoquinolinones and a chance to study their biological activities.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.3c01032