Metal-free [2 + 2 + 1] annulation of alkynes, nitriles, and oxygen atoms: iodine(III)-mediated synthesis of highly substituted oxazoles

Akio Saito; Akihiro Taniguchi; Yui Kambara; Yuji Hanzawa

doi:10.1021/ol4009816

Metal-free [2 + 2 + 1] annulation of alkynes, nitriles, and oxygen atoms: iodine(III)-mediated synthesis of highly substituted oxazoles

Org Lett. 2013 Jun 7;15(11):2672-5. doi: 10.1021/ol4009816. Epub 2013 May 22.

Authors

Akio Saito¹, Akihiro Taniguchi, Yui Kambara, Yuji Hanzawa

Affiliation

¹ Division of Applied Chemistry, Institute of Engineering, Tokyo University of Agriculture and Technology, Koganei, Tokyo 184-8588, Japan. akio-sai@cc.tuat.ac.jp

PMID: 23698073
DOI: 10.1021/ol4009816

Abstract

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.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

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

Substances

Alkynes
Anti-Inflammatory Agents
Metals
Nitriles
Oxazoles
Iodine
Oxygen