Direct access to 4-carboxy-1,8-naphthyridines and related compounds through Pfitzinger-type chemistry.
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.
Zong
Ruifa
R
Department of Chemistry, 136 Fleming Building, University of Houston, Houston, TX 77204-5003, USA.
Zhou
Hui
H
Thummel
Randolph P
RP
D009682:Magnetic Resonance Spectroscopy; D009287:Naphthyridines / Q000737:chemistry*; D019032:Spectrometry, Mass, Matrix-Assisted Laser Desorption-Ionization
D009287:Naphthyridines