Oxidative Aza-Annulation of Enynyl Azides to 2-Keto/Formyl-1H-pyrroles

J Org Chem. 2017 Jan 20;82(2):944-949. doi: 10.1021/acs.joc.6b02468. Epub 2017 Jan 9.

Abstract

A method for the construction of pyrroles bearing a 2-keto or formyl group through the intramolecular oxidative aza-annulation of enynyl azides is reported for the first time. It involves a sequential carbon-nitrogen/carbon-oxygen bond formations, and the combination of AuCl3 with AgSbF6 was identified as a suitable reagent system to promote the present reaction. The required enynyl azides are readily prepared from Morita-Baylis-Hillman (MBH) acetates of acetylenic aldehydes.

Publication types

  • Research Support, Non-U.S. Gov't