Rapid microwave-assisted Biginelli synthesis of bioactive heterocycles

CHED 234

Marissa B. Sherman, sherma_m@denison.edu, Eric Schurter, Kimberly M. Specht, spechtk@denison.edu, and Thomas A. Evans, evans@denison.edu. Department of Chemistry and Biochemistry, Denison University, Ebaugh Laboratories, Granville, OH 43023
The impressive biological activity of dihydropyrimidines accounts for the strong current interest in the Biginelli reaction, a one-pot reaction involving urea, an acetoacetic ester and an aryl aldehyde. We have developed a robust, microwave-assisted, microscale version of the Biginelli reaction in which copper(II)aspirinate is used to promote the reaction. This method yields material suitable for spectroscopic analysis well within the constraints of a three-hour laboratory and offers many alternatives for an inquiry-based laboratory experience.