Mild and Regioselective N-Alkylation of 2-Pyridones in Water

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• 作者：Xin Hao ; Zhongmiao Xu ; Hongfu Lu ; Xuedong Dai ; Ting Yang ; Xichen Lin ; Feng Ren
• 刊名：Organic Letters
• 出版年：2015
• 出版时间：July 17, 2015
• 年：2015
• 卷：17
• 期：14
• 页码：3382-3385
• 全文大小：305K
• ISSN：1523-7052

文摘

A mild and regioselective N-alkylation reaction of 2-pyridones in water has been developed. Tween 20 (2% w/w) was added to create a micellar system for improved solubility of starting materials, which leads to enhanced reaction rates. The protocol demonstrated a wide substrate scope with good isolated yields (40鈥?4%) for all of the 24 examples evaluated. High regioselectivity favoring N-alkylation over O-alkylation was observed for benzyl halides (>5:1), primary alkyl halides (>6:1), and bulky and less reactive secondary alkyl halides (>2.4:1).