General synthetic methods for the preparation of 1-substituted-vinyl-2-pyridones |
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Authors: | Patrick S Mariano Emil Krochmal Ralph Beamer Peter L Huesmann Debra Dunaway-Mariano |
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Institution: | Department of Chemistry, Texas A&M University, College Station, TX 77843, U.S.A. |
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Abstract: | General methods for the preparation of a variety of 1-substituted vinyl-2-pyridones are described. Synthetic routes followed involve (1) nucleophilic substitution reaction of the 2-hydroxy-pyridyl anion of haloolefins containing β-activating groups, such as carbonyl and phenyl, (2) elimination reactions of ester derivatives of 1-pyridonyl-2-ethanols and (3) base catalyzed isomerizations of 1-allyl-2-pyridones. The details involved with each of the synthetic methods and purification of the derived 1-vinyl-2-pyridones are described. Additionally important spectroscopic properties of compounds in this series are discussed in terms of preferred conformations about the nitrogen-exocyclic vinyl carbon bond. |
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