Indium-Catalyzed Aromative Spiro Coupling of Quinones with Oxindoles for Highly Functionalized Xanthenes as Efficient Fluorophores

Org Lett. 2021 Feb 19;23(4):1383-1387. doi: 10.1021/acs.orglett.1c00042. Epub 2021 Feb 2.

Abstract

A convenient and an efficient protocol for the assembly of diverse xanthenes bearing a biologically interesting oxindole nucleus is developed by utilizing the In(III)-catalyzed spiro coupling of 1,4-benzoquinones or 1,4-naphthoquinones with oxindoles. This novel protocol proceeds via a cascade of double Michael additions and intramolecular cyclization. The synthesized compounds have potential use as fluorophores for the selective imaging of heavy metals in living cells.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Catalysis
  • Cyclization
  • Fluorescent Dyes / chemistry*
  • Indium / chemistry*
  • Ionophores / chemistry*
  • Molecular Structure
  • Oxindoles / chemistry*
  • Quinones / chemistry*
  • Xanthenes / chemical synthesis
  • Xanthenes / chemistry*

Substances

  • Fluorescent Dyes
  • Ionophores
  • Oxindoles
  • Quinones
  • Xanthenes
  • Indium