title: Synthetic entries to substituted bicyclic pyridones.
abstract: The synthesis of 6,6- and 5,6-bicyclic pyridone scaffolds has been completed using (i) an intramolecular Mitsunobu reaction and/or (ii) hydrolysis of a bicyclic pyridinium salt intermediate. Regioselective functionalization of the pyridone ring has been achieved via either direct lithiation or use of the "halogen dance" reaction. Suzuki coupling then allows introduction of aryl units at C(7)/C(9) or C(8) onto the bicyclic pyridone scaffold at either an early or late stage in the synthetic sequence. Suzuki couplings involving iodopyridinium intermediates are particularly effective.
authors.affiliation: School of Chemistry, University of Bristol, Bristol, BS8 1TS, UK.
authors.forename: Dachen
authors.initials: D
authors.lastname: Cheng
authors.forename: Laura
authors.initials: L
authors.lastname: Croft
authors.forename: Muna
authors.initials: M
authors.lastname: Abdi
authors.forename: Andrew
authors.initials: A
authors.lastname: Lightfoot
authors.forename: Timothy
authors.initials: T
authors.lastname: Gallagher
mesh_terms: D006574:Heterocyclic Compounds, 2-Ring / Q000138:chemical synthesis* / Q000737:chemistry; D017613:Iodine Compounds / Q000138:chemical synthesis / Q000737:chemistry; D007536:Isomerism; D015394:Molecular Structure; D011728:Pyridones / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: D006574:Heterocyclic Compounds, 2-Ring; D017613:Iodine Compounds; D011728:Pyridones