One-pot synthesis of dibenzo[b,h][1,6]naphthyridines from 2-acetylaminobenzaldehyde: application to a fluorescent DNA-binding compound

Chem Commun (Camb). 2014 Dec 21;50(98):15525-8. doi: 10.1039/c4cc07807a. Epub 2014 Oct 30.

Abstract

Dibenzo[b,h][1,6]naphthyridines were synthesized in one pot by reacting 2-acetylaminobenzaldehyde with methyl ketones under basic conditions via four sequential condensation reactions. This method was also applied to the synthesis of 1,2-dihydroquinolines. 6-Methyl-1,6-dibenzonaphthyridinium triflates showed strong fluorescence, and the fluorescence intensities were changed upon intercalation into double-stranded DNA.

MeSH terms

  • Benzaldehydes / chemistry
  • DNA / chemistry*
  • Fluorescence
  • Fluorescent Dyes / chemical synthesis*
  • Fluorescent Dyes / chemistry
  • Intercalating Agents / chemical synthesis*
  • Intercalating Agents / chemistry
  • Ketones / chemistry
  • Naphthyridines / chemical synthesis*
  • Naphthyridines / chemistry
  • Quinolines / chemical synthesis
  • Quinolines / chemistry

Substances

  • 1,4-dihydroquinoline
  • Benzaldehydes
  • Fluorescent Dyes
  • Intercalating Agents
  • Ketones
  • Naphthyridines
  • Quinolines
  • DNA