Pyrazole-based pharmaceuticals treat a wide array of diseases and conditions including obesity, diabetes, cancer, microbial and viral infections, pain and inflammation, and many neurological disorders. Syntheses for this biologically significant substrate have been well developed, but fluorinated pyrazoles remain to be directly accessible. By 2013, over 25% of all drugs available on the market contained the element fluorine due to its unique characteristics leading to improved target protein binding, bioavailability, and metabolic stability. In order to harness these pharmaceutical benefits of fluorine and overcome its difficulty in handling and stability, our lab sets out to develop new synthetic methods to achieve fluorinated heterocycles. From our recent studies we found that fluoronitroalkenes can be employed in regioselective [3+2] dipolar cycloaddition reaction with organic azides to generate 1,5-disubstituted-fluorinated-1,2,3-triazoles Here we show fluoronitroalkenes participate in regioselective cycloaddition in a similar fashion to afford fluorinated pyrazoles from organic hydrazones prepared <i>in situ</i>.

One-pot synthesis of fluorinated pyrazoles from fluoroalkenes

Macromolecular Chemistry: The Second Century

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ACS Spring 2020 National Meeting & Expo

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