Direct access to 4-carboxy-1,8-naphthyridines and related compounds through Pfitzinger-type chemistry

J Org Chem. 2008 Jun 6;73(11):4334-7. doi: 10.1021/jo800456r. Epub 2008 May 8.

Abstract

The 4-carboxy-1,8-naphthyrid-2-yl moiety is a useful ligand component in that it promotes lower energy electronic absorption in its metal complexes and also provides a useful tether for anchoring the ligand to a semiconductor surface. The synthon [2-(pivaloylamino)pyrid-3-yl]oxoacetic acid ethyl ester can be easily obtained in two steps from 2-aminopyridine. The Pfitzinger-type condensation of this molecule with a 2-acetylazaaromatic species in ethanolic KOH, after acidification, directly provides bi- and tridentate ligands containing the 4-carboxy-1,8-naphthyrid-2-yl moiety.

Publication types

  • Research Support, Non-U.S. Gov't
  • Research Support, U.S. Gov't, Non-P.H.S.

MeSH terms

  • Magnetic Resonance Spectroscopy
  • Naphthyridines / chemistry*
  • Spectrometry, Mass, Matrix-Assisted Laser Desorption-Ionization

Substances

  • Naphthyridines