Synthesis of Azacarbolines via PhIO2-Promoted Intramolecular Oxidative Cyclization of α-Indolylhydrazones

J Org Chem. 2021 Dec 17;86(24):17918-17929. doi: 10.1021/acs.joc.1c02217. Epub 2021 Dec 6.

Abstract

An unprecedented synthesis of polysubstituted indole-fused pyridazines (azacarbolines) from α-indolylhydrazones under oxidative conditions using a combination of iodylbenzene (PhIO2) and trifluoroacetic acid (TFA) has been developed. This transformation is conducted without the need for transition metals, harsh conditions, or an inert atmosphere.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Cyclization
  • Oxidation-Reduction
  • Oxidative Stress*
  • Trifluoroacetic Acid

Substances

  • Trifluoroacetic Acid