Friedländer approach for the incorporation of 6-bromoquinoline into novel chelating ligands.
Nitration of 3-bromobenzaldehyde followed by sodium dithionite reduction provides 5-bromo-2-aminobenzaldehyde, which undergoes the Friedländer condensation with a variety of enolizable ketones to afford bidentate and tridentate 6-bromoquinoline derivatives. These species may be dimerized with Ni(0) to form biquinolines or treated under Sonogashira conditions to afford 6-alkynyl derivatives. Examination of optical properties indicate an unusually high emission quantum yield for 6,6'-biquinolines. [structure: see text]
Hu
Yi-Zhen
YZ
Department of Chemistry, University of Houston, Houston, TX 77204-5003, USA.
Zhang
Gang
G
Thummel
Randolph P
RP