Copper-Catalyzed Tandem Decyclization-Cyclization Reaction of N-Alkynyl-3-hydroxyisoindolin-1-ones Generated from N-Alkynyl Phthalimides: Selective Synthesis of ortho-(2-Oxazolyl)phenyl Ketones

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• 作者：Takuya Sueda ; Noriko Okamoto ; Reiko Yanada
• 刊名：Journal of Organic Chemistry
• 出版年：2016
• 出版时间：July 1, 2016
• 年：2016
• 卷：81
• 期：13
• 页码：5745-5751
• 全文大小：356K
• 年卷期：0
• ISSN：1520-6904

文摘

Selective carbophilic monoaddition on N-alkynyl phthalimides was performed with organometallic reagents to afford 3-substituted N-alkynyl-3-hydroxyisoindolin-1-ones (α-hydroxy ynamides) as a new subgroup of ynamides. Owing to the alkynyl motif on the nitrogen atom, α-hydroxy ynamides were easily isomerized to the corresponding ortho-(2-oxazolyl)phenyl ketones in a CuCl-catalyzed tandem decyclization–cyclization reaction under mild conditions.