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

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 re...

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Bibliographic Details
Published in:Tetrahedron letters 2002-02, Vol.43 (6), p.951-954
Main Authors: Chang, Junbiao, Zhao, Kang, Pan, Shifeng
Format: Article
Language:English
Subjects:
2-arylbenzoxazoles
DDQ
ion-exchange resin
library
oxidation
solution phase
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Summary: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. A 352-member library has been synthesized by this solution-phase strategy.
ISSN:0040-4039
1873-3581
DOI:10.1016/S0040-4039(01)02302-4