Intramolecular 1, 6-addition to 2-pyridones. Mechanism and synthetic scope.

…, C Hirschhäuser, P Magrone

Index: Gallagher, Timothy; Derrick, Ian; Durkin, Patrick M.; Haseler, Claire A.; Hirschhaeuser, Christoph; Magrone, Pietro Journal of Organic Chemistry, 2010 , vol. 75, # 11 p. 3766 - 3774

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Citation Number: 23

Abstract

The scope and limitations of the intramolecular 1, 6-addition of an enolate to a 2-pyridone moiety, a reaction that has found application in the synthesis of the lupin alkaloids, have been probed. This nucleophilic addition process has been shown to be reversible and favored in the case of (less stabilized) amide and lactam enolates, which readily form five- and six-membered bi-/tricyclic products. Alternative enolates (ketone, ester, thiolactam) ...