Synthesis of 3-cyano-2-pyridones from malononitrile : an honors thesis (HONRS 499)

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Authors
Huehls, Christopher B.
Kite, Camille M.
Advisor
Sammelson, Robert E.
Issue Date
2009
Keyword
Degree
Thesis (B.?.)
Department
Honors College
Other Identifiers
Abstract

Substituted pyridones have multiple known uses in medicinal chemistry including topoisomerase inhibition in anticancer medicines. Cerpegin, a naturally occurring 2-pyridone, functions as an analgesic, anti-ulcer, tranquilizer, and anti-inflammatory. 2-Pyridones have also been associated with antitumor, antifungal, antibacterial, antiviral, and antithrombotic properties. Deri( atives of 2-pyridones are currently being researched as inhibitors of HIV-1 replication. Recently the condensation reaction of malononitrile with aldehydes and ketones has been examined. This condensation is extended to the uncatalyzed reaction of f3-diketones. This reaction requires two equivalents of malononitrile and produces 3-cyano-2-pyridones. An intermediate that provides information about possible mechanistic routes has also been isolated. The reaction pathway explored is ineffective in 13-diektones with large steric hindrances. Single products or multiple isomers in mixed ratios are obtained.