Expedient Synthesis of 伪-(2-Azaheteroaryl) Acetates via the Addition of Silyl Ketene Acetals to Azine-N-oxides

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• 作者：Allyn T. Londregan ; Kristen Burford ; Edward L. Conn ; Kevin D. Hesp
• 刊名：Organic Letters
• 出版年：2014
• 出版时间：June 20, 2014
• 年：2014
• 卷：16
• 期：12
• 页码：3336-3339
• 全文大小：250K
• 年卷期：v.16,no.12(June 20, 2014)
• ISSN：1523-7052

文摘

A new and expedient synthesis of 伪-(2-azaheteroaryl) acetates is presented. The reaction proceeds rapidly under mild conditions via the addition of silyl ketene acetals to azine-N-oxides in the presence of the phosphonium salt PyBroP. This procedure affords diverse 伪-(2-azaheteroaryl) acetates which are highly desirable components/building blocks in molecules of pharmaceutical interest but are traditionally challenging to synthesize via contemporary methods. The reaction optimization and mechanism as well as a novel electronically enhanced PyBroP derivative are described.