Emmanuel Ferrer Flegeau,Matthew E. Popkin, andMichael F. Greaney*
University of Edinburgh, School of Chemistry, Joseph Black Building,
King's Buildings, West Mains Road, Edinburgh, EH9 3JJ, U.K., and
GlaxoSmithKline, Chemical Development, Old Powder Mills,
Tonbridge, Kent, TN11 9AN, U.K.
Michael.Greaney@ed.ac.uk
Received March 10, 2006
Abstract:
A protocol for the functionalization of the oxazole 2- and 4-positions using the Suzuki coupling reaction is described. 2-Aryl-4-trifloyloxazoles
undergo rapid, microwave-assisted coupling with a range of aryl and heteroaryl boronic acids in good to excellent yields. The methodology
is similarly effective using 4-aryl-2-chlorooxazoles as the coupling partner and has been extended to the synthesis of a novel class of homo-
and heterodimeric 4,4-linked dioxazoles.