Efficient two-step synthesis of 9-aryl-6-hydroxy-3H-xanthen-3-one fluorophores.
[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.
Bacci
James P
JP
Department of Chemistry, University of California, Irvine, 92697-2025, USA.
Kearney
Aaron M
AM
Van Vranken
David L
DL
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*
D001547:Benzaldehydes; D014966:Xanthenes; D005461:Fluorine