Metal-Free Annulation of Arenes with 2-Aminopyridine Derivatives: The Methyl Group as a Traceless Non-Chelating Directing Group

A novel annulation reaction between 2‐aminopyridine derivatives and arenes under metal‐free conditions is described. The presented intermolecular transformation provided straightforward access to the important pyrido[1,2‐a]benzimidazole scaffold under mild reaction conditions. The unprecedented appl...

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Veröffentlicht in:Angewandte Chemie International Edition 2014-07, Vol.53 (31), p.8163-8166
Hauptverfasser: Manna, Srimanta, Matcha, Kiran, Antonchick, Andrey P.
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Sprache:eng
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Zusammenfassung:A novel annulation reaction between 2‐aminopyridine derivatives and arenes under metal‐free conditions is described. The presented intermolecular transformation provided straightforward access to the important pyrido[1,2‐a]benzimidazole scaffold under mild reaction conditions. The unprecedented application of the methyl group of methylbenzenes as a traceless, non‐chelating, and highly regioselective directing group is reported. Disappearing Me: A novel selective annulation between 2‐aminopyridine derivatives and arenes under metal‐free conditions provides the important pyrido[1,2‐a]benzimidazole scaffold under mild reaction conditions. In this intermolecular reaction the methyl group of methylbenzenes serves as a traceless, non‐chelating, and highly regioselective directing group.
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.201403712