title: Synthesis of 8-heteroaryl nitroxoline analogues via one-pot sequential Pd-catalyzed coupling reactions.
abstract: A series of 8-heteroaryl substituted quinolines were prepared, either by direct C-H arylation of five-membered heteroarenes, or Pd-catalyzed coupling of organoboron reagents with bromoquinolines. The use of (benzo)thiophenyl or (benzo)furanyl boron coupling partners allowed further C-H functionalization on the five-membered heteroaryl ring with aryl bromides in one flask to access a variety of polyconjugated molecular architectures. The developed methodology represents a simple approach towards 8-arylated analogues of the biologically interesting nitroxoline core.
authors.affiliation: Faculty of Chemistry and Chemical Technology, University of Ljubljana, Večna pot 113, SI-1000 Ljubljana, Slovenia. bogdan.stefane@fkkt.uni-lj.si.
authors.forename: Helena
authors.initials: H
authors.lastname: Brodnik
authors.affiliation: Faculty of Chemistry and Chemical Technology, University of Ljubljana, Večna pot 113, SI-1000 Ljubljana, Slovenia. bogdan.stefane@fkkt.uni-lj.si.
authors.forename: Franc
authors.initials: F
authors.lastname: Požgan
authors.affiliation: Faculty of Chemistry and Chemical Technology, University of Ljubljana, Večna pot 113, SI-1000 Ljubljana, Slovenia. bogdan.stefane@fkkt.uni-lj.si.
authors.forename: Bogdan
authors.initials: B
authors.lastname: Štefane
mesh_terms: D002384:Catalysis; D015394:Molecular Structure; D009600:Nitroquinolines / Q000138:chemical synthesis* / Q000737:chemistry*; D009942:Organometallic Compounds / Q000737:chemistry*; D010165:Palladium / Q000737:chemistry*
chemical_list: D009600:Nitroquinolines; D009942:Organometallic Compounds; D010165:Palladium; C005308:nitroxoline