Insertion-coupling-cycloisomerization domino synthesis and cation-induced halochromic fluorescence of 2,4-diarylpyrano[2,3-b]indoles

Org Lett. 2010 Sep 17;12(18):4122-5. doi: 10.1021/ol101709p.

Abstract

2,4-Diarylpyrano[2,3-b]indoles are formed via a Pd-Cu-catalyzed insertion-coupling-cycloisomerization domino reaction in moderate yields. Although the tricyclic systems are nonfluorescent in solution, protonation, quaternation, or complexation with metal ions induces intense green luminescence. Most strikingly, selective halochromic fluorescence of zinc and magnesium over calcium ions classify the title compounds as metal-selective luminescence sensors.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Cations / chemistry
  • Crystallography, X-Ray
  • Cyclization
  • Fluorescent Dyes / chemical synthesis*
  • Indoles / chemistry*
  • Isomerism
  • Methylation
  • Models, Molecular
  • Molecular Structure

Substances

  • Cations
  • Fluorescent Dyes
  • Indoles