Synthesis of 2-arylbenzoxazoles via DDQ promoted oxidative cyclization of phenolic Schiff bases - A solution-phase strategy for library synthesis

Article abstract of DOI:10.1016/S0040-4039(01)02302-4

The Schiff base derived from the condensation of o-aminophenol with benzaldehydes was induced to undergo oxidative cyclization in the presence of DDQ. The resulting 2-arylbenzoxazoles were separated from the reduced DDQ by product by treatment of reaction mixture with a strongly basic ion-exchange resin. The applicability of this chemistry to spatially separate library synthesis is demonstrated by the preparation of a 352-member library.