Intramolecular 1,6-Addition to 2-Pyridones. Mechanism and Synthetic Scope.

详细信息    查看全文

• 作者：Timothy Gallagher ; Ian Derrick ; Patrick M. Durkin ; Claire A. Haseler ; Christoph Hirschhuser ; Pietro Magrone
• 刊名：Journal of Organic Chemistry
• 出版年：2010
• 出版时间：June 4, 2010
• 年：2010
• 卷：75
• 期：11
• 页码：3766-3774
• 全文大小：1046K
• 年卷期：v.75,no.11(June 4, 2010)
• ISSN：1520-6904

文摘

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) and a variety of different acceptors (isoquinolinone, pyrimidinone, pyrazinone, pyridopyrazinone) have been evaluated, and a range of competing side reactions have been identified and characterized using various techniques, including in situ IR.