Chalcones are organic molecules consisting of two aromatic rings connected by an enone, creating a completely delocalized π-electron system that have been shown to have a myriad of interesting biological effects. Heterocyclic chalcones especially have been shown to have antibacterial and antifungal effects and could potentially have medical applications. The purpose of this research was to better understand the challenges of synthesizing heterocyclic chalcones. After a preliminary test using 4-chlorobenzaldehyde and 4-methoxylacetophenone, a variety of substituted benzaldehydes were reacted with 2-furyl methyl ketone and 2-acetyl thiophene using Claisen-Schmitt condensation to create heterocyclic chalcones. Multiple reaction conditions such as base catalyst, heat, and reaction time were compared, as well as product recovery methods. The chalcones were analyzed using melting point, GC/MS, and IR spectroscopy. The success of the reactions was found to be largely dependent on the electron withdrawing effects of the substituents on the aromatic aldehyde, and it was observed that the strength of the catalyst base and the method of product recovery impacted the quality of the recovered product.

Synthesis of heterocyclic chalcones

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

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