The majority of current drug candidates include nitrogen-containing rings such as pyridine, as many others contain sulfonamides, well recognized for their great capabilities as antibiotic agents. However, limited research has been pursued regarding compounds which proximally join these sulfonamide and pyridine functional groups. Previous investigations in our laboratory resulted in the successful synthesis of the N-(2-(pyridin-2-yl)ethyl)sulfonamide scaffold via conjugate addition of benzenesulfonamide to 2-vinylpyridine under solvent-free conditions. This current presentation outlines progress that has been made toward the synthesis of differentially substituted N-(2-(pyridin-2-yl)ethyl)sulfonamides employing vinylpyridines of varying acceptor activity, including electron donating, electron withdrawing, and sterically imposing groups at the five and six positions of the pyridine ring. It is hypothesized that variable substitution will display a linear free energy Hammett relationship on the rate of the conjugate addition reaction, as well as significantly impact the biological activities of the resultant N-(2-(pyridin-2-yl)ethyl)sulfonamide substrates.

Synthesis and reactivity of differentially substituted 2-vinylpyridines in the conjugate addition of benzenesulfonamide

243rd National Meeting (2012)

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