Oxazoles are important heterocycles found in natural and synthetic compounds. The ability to regioselectively assemble highly functionalized oxazoles would further facilitate development of pharmaceuticals and allow greater access to biologically relevant compounds. Recently, our group developed a rapid synthesis of highly substituted 2,4-diamido-5-aminooxazoles by reacting an isonitrile amide with isocyanates in a three-component reaction. A wide variety of isonitrile and isocyanate reactants were combined to produce a library of tri-substituted oxazoles. In this study the impact of the amido group of the isonitrile on the multi-component reaction was investigated. It was found that secondary amides led to lower yields of cyclized amino-oxazole products, while tertiary amides produced the highest yields. The influence of the amide group on the relative ratio of constitutional isomer products was also investigated. Future work on our mechanistic investigation will be used to develop our library of highly-substituted oxazoles for biological screening.

Effects of an amide group on a multicomponent synthesis of highly substituted oxazoles

2019 Spring National Meeting

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