N-Bromosuccinimide promoted and base switchable one pot synthesis of α-imido and α-amino ketones from styrenes

Org Biomol Chem. 2016 Jan 21;14(3):858-61. doi: 10.1039/c5ob02034d. Epub 2015 Dec 10.

Abstract

An N-Bromosuccinimide (NBS) promoted one pot strategy for the synthesis of α-amino functionalized aryl ketones starting from commercially available styrenes has been developed. NBS participates in multiple tasks, such as bromonium ion formation, oxidation of bromohydrin and providing a nucleophilic nitrogen source. The reaction can easily be switched between α-imido and α-amino ketones by the choice of base. This one pot strategy was successfully applied for the synthesis of psychoactive drug candidates, amfepramone, mephedrone and 4-MEC.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Amines / chemistry*
  • Bromosuccinimide / chemistry*
  • Imides / chemistry*
  • Ketones / chemical synthesis*
  • Ketones / chemistry
  • Molecular Structure
  • Styrenes / chemistry*

Substances

  • Amines
  • Imides
  • Ketones
  • Styrenes
  • Bromosuccinimide