A convenient preparation of xanthene dyes.
A facile synthetic route utilizing readily available reagents affords a series of regioisomerically pure xanthene dye derivatives. Advantages include relatively mild conditions and good to excellent yields. Nonpolar, highly crystalline intermediates are isolable by standard chromatographic techniques. The intermediates are in the requisite xanthene oxidation state, thus avoiding the need for relatively inefficient oxidation chemistry and/or harsh conditions. During the course of this work, a new boron-mediated 1,2-aryl migration reaction was discovered.
Yang
Youjun
Y
Department of Chemistry, Louisiana State University, Baton Rouge, LA 70803, USA.
Escobedo
Jorge O
JO
Wong
Alexander
A
Schowalter
Corin M
CM
Touchy
Michael C
MC
Jiao
Lijuan
L
Crowe
William E
WE
Fronczek
Frank R
FR
Strongin
Robert M
RM
D004396:Coloring Agents / Q000138:chemical synthesis* / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D008958:Models, Molecular; D019032:Spectrometry, Mass, Matrix-Assisted Laser Desorption-Ionization; D014966:Xanthenes / Q000138:chemical synthesis* / Q000737:chemistry
D004396:Coloring Agents; D014966:Xanthenes