Preparation of N-Alkyl 2-Pyridones via a Lithium Iodide Promoted O- to N-Alkyl Migration: Scope and Mechanism
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- 作者：Sarah Z. Tasker ; Michael A. Bosscher ; Christina A. Shandro ; Erica L. Lanni ; Keun Ah Ryu ; Gregory S. Snapper ; Jarrad M. Utter ; Bruce A. Ellsworth ; Carolyn E. Anderson
- 刊名：The Journal of Organic Chemistry
- 出版年：2012
- 出版时间：September 21, 2012
- 年：2012
- 卷：77
- 期：18
- 页码：8220-8230
- 全文大小：496K
- 年卷期：v.77,no.18(September 21, 2012)
- ISSN：1520-6904
文摘
An efficient and inexpensive LiI-promoted O- to N-alkyl migration of 2-benzyloxy-, 2-allyloxy-, and 2-propargyloxypyridines and heterocycles is reported. The reaction produces the corresponding N-alkyl 2-pyridones and analogues under green, solvent-free conditions in good to excellent yields (30 examples, 20鈥?7% yield). This method has been shown to be intermolecular and requires heat and lithium cation to occur.