Metal-Free [2 + 2 + 1] Annulation of Alkynes, Nitriles, and Oxygen Atoms: Iodine(III)-Mediated Synthesis of Highly Substituted Oxazoles

Metal-Free [2 + 2 + 1] Annulation of Alkynes, Nitriles, and Oxygen Atoms: Iodine(III)-Mediated Synthesis of Highly Substituted Oxazoles

The metal-free [2 + 2 + 1] annulation of alkynes, nitriles, and O-atoms for the regioselective assembly of 2,4-disubstituted and 2,4,5-trisubstituted oxazole compounds has been achieved by the use of PhIO with TfOH or Tf2NH. The present reaction could be applied to a facile synthesis of an anti-infl...

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Veröffentlicht in:Organic letters 2013-06, Vol.15 (11), p.2672-2675
Hauptverfasser: Saito, Akio, Taniguchi, Akihiro, Kambara, Yui, Hanzawa, Yuji
Format: Artikel
Sprache:eng
Schlagworte:
Alkynes - chemistry
Anti-Inflammatory Agents - chemical synthesis
Anti-Inflammatory Agents - chemistry
Catalysis
Iodine - chemistry
Metals - chemistry
Molecular Structure
Nitriles - chemistry
Oxazoles - chemical synthesis
Oxygen - chemistry
Stereoisomerism
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Zusammenfassung:The metal-free [2 + 2 + 1] annulation of alkynes, nitriles, and O-atoms for the regioselective assembly of 2,4-disubstituted and 2,4,5-trisubstituted oxazole compounds has been achieved by the use of PhIO with TfOH or Tf2NH. The present reaction could be applied to a facile synthesis of an anti-inflammatory drug.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol4009816