Yb(OTf) 3 ‐Catalyzed C=C Bond Cleavage‐Reassembly Enabling Bicyclization: Regioselective Synthesis of Heteroarylated Pentacyclic Indoles

An Yb(OTf) 3 ‐catalyzed [2+2] cycloaddition /retro‐electrocyclization (CA‐RE)/bicyclization of 1‐(2‐aminoarylaklynyl)‐naphthalen‐2‐ols and 3‐alkylideneoxindoles is reported, enabling a direct C=C bond cleavage‐reassembly process to regioselectively synthesize a variety of quinoline‐tethered benzo[5,...

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Published in:Advanced synthesis & catalysis 2024-10
Main Authors: Liu, Zi‐Li, Zhu, Chi‐Fan, Liu, Yin‐Ping, Chen, Ke, Li, Qiu‐Yun, Wang, Shu‐Liang, Hao, Wen‐Juan, Jiang, Bo
Format: Article
Language:English
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Summary:An Yb(OTf) 3 ‐catalyzed [2+2] cycloaddition /retro‐electrocyclization (CA‐RE)/bicyclization of 1‐(2‐aminoarylaklynyl)‐naphthalen‐2‐ols and 3‐alkylideneoxindoles is reported, enabling a direct C=C bond cleavage‐reassembly process to regioselectively synthesize a variety of quinoline‐tethered benzo[5,6]chromeno[2,3‐ b ]indoles in 31–84% yields. Exchanging the amino group for a hydroxyl group in the arylalkynyl unit of the naphthalen‐2‐ol substrate resulted in chromenyl chromeno[2,3‐ b ]indoles via a similar cascade process.
ISSN:1615-4150
1615-4169
DOI:10.1002/adsc.202400995