title: Efficient two-step synthesis of 9-aryl-6-hydroxy-3H-xanthen-3-one fluorophores.
abstract: [reaction: see text] A two-step method for the synthesis of 9-aryl-6-hydroxy-3H-xanthen-3-one fluorophores involving condensation of aryl aldehydes and fluororesorcinol is shown to proceed through a triarylmethane intermediate. The condensation is complicated by retro-Friedel-Crafts reactions which can be minimized by controlling the amount of acid. The xanthenone ring system is prepared by a final oxidative cyclization with DDQ.
authors.affiliation: Department of Chemistry, University of California, Irvine, 92697-2025, USA.
authors.forename: James P
authors.initials: JP
authors.lastname: Bacci
authors.forename: Aaron M
authors.initials: AM
authors.lastname: Kearney
authors.forename: David L
authors.initials: DL
authors.lastname: Van Vranken
mesh_terms: D001547:Benzaldehydes / Q000737:chemistry; D003500:Cyclization; D005461:Fluorine / Q000737:chemistry*; D006900:Hydroxylation; D015394:Molecular Structure; D010084:Oxidation-Reduction; D014966:Xanthenes / Q000138:chemical synthesis / Q000737:chemistry*
chemical_list: D001547:Benzaldehydes; D014966:Xanthenes; D005461:Fluorine