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

✍ Scribed by Junbiao Chang; Kang Zhao; Shifeng Pan

• Publisher: Elsevier Science
• Year: 2002
• Tongue: French
• Weight: 88 KB
• Volume: 43
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(01)02302-4

✦ Synopsis

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 byproduct 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.