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Metal-free switchable: Ortho/ipso -cyclization of N -aryl alkynamides: Divergent synthesis of 3-selenyl quinolin-2-ones and azaspiro[4,5]trienones
Gowri Sankar Grandhi, Isai Ramakrishna,
Published in Royal Society of Chemistry
2019
PMID: 31777902
Volume: 17
   
Issue: 48
Pages: 10163 - 10166
Abstract
A selenium radical triggered switchable ortho/ipso-cyclization cascade of N-aryl alkynamides has been devised under metal-free conditions to access 3-selenyl quinolin-2-ones and 3-selenospiro[4,5]trienones in high yields (up to 98%). The simple protocol is scalable and the mechanistic studies suggest that the radical cascade proceeds through a spirocyclic intermediate which is formed via an intramolecular ipso-cyclization route. © 2019 The Royal Society of Chemistry.
About the journal
JournalData powered by TypesetOrganic and Biomolecular Chemistry
PublisherData powered by TypesetRoyal Society of Chemistry
ISSN14770520
Open AccessNo
Concepts (12)
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    Chemistry
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    Positive ions
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    DIVERGENT SYNTHESIS
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    High yield
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    Mechanistic studies
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    Metal free
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    METAL-FREE CONDITIONS
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    SIMPLE PROTOCOL
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    SWITCHABLE
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    Cyclization
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    Article
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    Synthesis