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

被引：33
作者：
Gallagher, Timothy [1 ]
Derrick, Ian [2 ]
Durkin, Patrick M. [1 ]
Haseler, Claire A. [1 ]
Hirschhaeuser, Christoph [1 ]
Magrone, Pietro [1 ]
机构：
[1] Univ Bristol, Sch Chem, Bristol BS8 1TS, Avon, England
[2] AstraZeneca, Proc Res & Dev, Avlon Works, Bristol BS10 7ZE, Avon, England
来源：
JOURNAL OF ORGANIC CHEMISTRY | 2010年 / 75卷 / 11期
基金：
英国工程与自然科学研究理事会;
关键词：
LITHIUM ALLYLDIBUTYLMAGNESATE; SMOKING-CESSATION; DERIVATIVES; CYCLIZATION;
D O I：
10.1021/jo100514a
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
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 etiolates, which readily form five- and six-membered bi-/tricyclic products. Alternative etiolates (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.
引用
收藏
页码：3766 / 3774
页数：9
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