Intramolecular Cyclization of Alkynyl 伪-Ketoanilide Utilizing [1,2]-Phospha-Brook Rearrangement Catalyzed by Phosphazene Base

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• 作者：Azusa Kondoh ; Takuma Aoki ; Masahiro Terada
• 刊名：Organic Letters
• 出版年：2014
• 出版时间：July 3, 2014
• 年：2014
• 卷：16
• 期：13
• 页码：3528-3531
• 全文大小：308K
• ISSN：1523-7052

文摘

A novel catalytic cyclization reaction of alkynyl 伪-ketoanilide was developed by utilizing the [1,2]-phospha-Brook rearrangement. This reaction involves the generation of an amide enolate via the umpolung process, that is the addition of dialkyl phosphite to a keto moiety followed by the [1,2]-phospha-Brook rearrangement, and the subsequent intramolecular addition of the enolate to an alkyne to afford 3,4-dihydro-2-quinolone derivatives. Under high-temperature reaction conditions, further rearrangement of the allylic phosphate moiety occurs to provide 2-quinolone derivatives.