Isoxazoles are a class of pharmaceutical compounds known for their anti-inflammatory, antiepileptic, and anticonvulsant properties. A greener isoxazole synthesis was devised by Bastin et al., and the universality of this synthesis was successfully tested with diverse acetophenone and benzaldehyde derivatives. This greener synthesis design takes into account the safety of the chemist and the environment by using safer reagents and solvents, significantly reducing waste, and optimizing yields. This project focused on the final step of the synthesis: the formation of the isoxazole ring from a dibromochalcone. To further optimize isoxazole formation, a microwave reactor was utilized to further reduce solvent and energy use. This initial study focused on the synthesis of 3-(4-methoxyphenyl)-5-phenylisoxazole and 5-(3-methylphenyl)-3-phenylisoxazole. Different parameters for temperature and reaction time were chosen in order to find the optimum parameters for isoxazole formation. The product was characterized by IR, NMR, and mass spectroscopy. The microwave reactor increased the yield of the product and decreased the solvent usage by approximately 75%. Future work includes testing the universality of the microwave reactor for use with other derivatives, using the microwave reactor on the other steps of the synthesis and a one-pot synthesis.

Use of a microwave reactor to synthesize isoxazoles

255th National Meeting (2018)

The official archive and repository for all ACS Meetings & Expositions abstracts and select posters or presentations.