Synthesis of Chalcogenylchromenes through Cyclization of Propargylic Aryl Ethers

J Org Chem. 2022 Nov 18;87(22):15050-15060. doi: 10.1021/acs.joc.2c01490. Epub 2022 Oct 27.

Abstract

We describe here for the first time the synthesis of 2-(chalcogenyl)-3H-benzo[f]chromenes and the new 3-(phenylselanyl)-2H-chromenes by the radical or electrophilic cyclization of propargylic aryl ethers in the presence of diorganyl diselenides or ditellurides using Oxone as a green oxidant and acetonitrile as solvent in a sealed tube at 100 °C. In this study, thirty-one chalcogenylchromenes with a broad substrate scope were prepared in moderate to excellent yields (50-98%), including compounds derived from natural products.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Benzopyrans* / chemistry
  • Cyclization
  • Ethers* / chemistry
  • Molecular Structure

Substances

  • propargyl ether
  • Ethers
  • Benzopyrans