ORGN 430

The oxazole moiety is an important structural motif that can be found in a diverse number of compounds such as organic dyes, non-linear optical materials, liquid crystals and pharmaceuticals. Benzobisoxazoles are of interest as they can be used as bi-functional building blocks for the synthesis of polymers containing that moiety. Typically, benzobisoxazoles are synthesized via condensation reactions at high temperatures. As a result the yields are usually low and dark tarry materials are often produced. We have developed a new approach toward the synthesis of functionalized benzobisoxazoles via condensation with an appropriate ortho ester.  These mild reactions conditions can produce benzobisoxazoles in high yields, which crystallize from the reaction mixture, resulting in the formation of pure products.