Unexpected Oxidative Ring Opening of Electron-Rich 3-Aminobenzofurans into α-Ketoimines Derivatives

Ilhem Khelifi; Guangkuan Zhao; Nour-Eddine Ghermani; Olivier Provot; Mouad Alami

doi:10.1021/acs.joc.8b01685

Unexpected Oxidative Ring Opening of Electron-Rich 3-Aminobenzofurans into α-Ketoimines Derivatives

J Org Chem. 2019 Feb 15;84(4):1725-1733. doi: 10.1021/acs.joc.8b01685. Epub 2018 Oct 29.

Authors

Ilhem Khelifi¹, Guangkuan Zhao¹, Nour-Eddine Ghermani², Olivier Provot¹, Mouad Alami¹

Affiliations

¹ Univ. Paris-Sud, BioCIS, CNRS, University Paris-Saclay, Equipe Labellisée Ligue Contre Le Cancer , F-92296 Châtenay-Malabry , France.
² Univ. Paris-Sud, Institut Galien Paris-Sud, CNRS, University Paris-Saclay , F-92296 Châtenay-Malabry , France.

PMID: 30352149
DOI: 10.1021/acs.joc.8b01685

Abstract

An unexpected ring opening of 3-aminobenzofurans promoted by NaO tBu in hot toluene, leading to a variety of α-ketoimines, is described. In the presence of 3-iodobenzofurans, NaO tBu mediates the 3-aminobenzofurans ring opening via a possible radical pathway without the help of any external radical sources.

Publication types

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