Synthesis of Pyridines and Pyrazines Using an Intramolecular Hydroamination-Based Reaction Sequence

Synthesis of Pyridines and Pyrazines Using an Intramolecular Hydroamination-Based Reaction Sequence

A management issue! Various pyridines and pyrazines can be efficiently accessed from simple acyclic precursors using an intramolecular hydroamination/isomerization/aromatization sequence (see scheme). p‐Toluenesulfonic acid (2 mol %) is used to catalyze this novel alkyne annulation, in which the oxi...

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Veröffentlicht in:Angewandte Chemie (International ed.) 2009-10, Vol.48 (44), p.8325-8327
Hauptverfasser: Rizk, Toni, Bilodeau, Eric J.-F, Beauchemin, André M
Format: Artikel
Sprache:eng
Schlagworte:
alkynes
Amination
Cyclization
homogeneous catalysis
hydroamination
Hydroxylamines - chemistry
nitrogen heterocycles
Pyrazines - chemical synthesis
Pyrazines - chemistry
Pyridines - chemical synthesis
Pyridines - chemistry
sustainable chemistry
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Zusammenfassung:A management issue! Various pyridines and pyrazines can be efficiently accessed from simple acyclic precursors using an intramolecular hydroamination/isomerization/aromatization sequence (see scheme). p‐Toluenesulfonic acid (2 mol %) is used to catalyze this novel alkyne annulation, in which the oxime group allows for a subsequent redox‐neutral aromatization step to occur.
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.200903922