Iodine-Promoted Oxidative Cyclization of Methyl Azaarenes and α-Amino Ketones for One-Pot Synthesis of 2-Azaaryl-5-aryl Oxazoles

J Org Chem. 2022 Sep 16;87(18):12460-12469. doi: 10.1021/acs.joc.2c01399. Epub 2022 Sep 6.

Abstract

A high efficiency protocol was developed for the synthesis of 2,5-disubstituted oxazoles via iodine-promoted oxidative domino cyclization. These reactions were performed with readily available methyl azaarenes and α-amino ketones under metal-free conditions. This protocol is a simple method with high functional group compatibility, a wide range of substrates, and excellent yield, providing a new way to synthesize azaarene-attached oxazoles.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Catalysis
  • Iodides
  • Iodine*
  • Ketones*
  • Molecular Structure
  • Oxazoles
  • Oxidative Stress

Substances

  • Iodides
  • Ketones
  • Oxazoles
  • Iodine