Intramolecular Nitrone Interrupted Click Reaction

We document the intramolecular interception of a Cu-catalyzed azidoalkyne cycloaddition employing a suitably placed nitrone group, providing a simple route to the unprecedented spiro-polyheterocyclic scaffold. The reaction is comprised of a Cu-catalyzed [3 + 2]-cycloaddition of (2-azidoaryl)­isatoge...

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Bibliographic Details
Published in:Organic letters 2024-03, Vol.26 (11), p.2233-2237
Main Authors: Pothi, Tejas A., Ramana, Chepuri V.
Format: Article
Language:English
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Summary:We document the intramolecular interception of a Cu-catalyzed azidoalkyne cycloaddition employing a suitably placed nitrone group, providing a simple route to the unprecedented spiro-polyheterocyclic scaffold. The reaction is comprised of a Cu-catalyzed [3 + 2]-cycloaddition of (2-azidoaryl)­isatogen with a terminal alkyne and the intramolecular trapping of the transient Cu-triazolide intermediate with the isatogen, with a net formation of one C–C and two C–N bonds and the new heterocyclic ring being spiro-annulated.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.4c00397