NH4I-Triggered [4 + 2] Annulation of α,β-Unsaturated Ketoxime Acetates with N-Acetyl Enamides for the Synthesis of Pyridines

Jindian Duan, Lei Zhang, Gaochen Xu, Heming Chen, Xiaojuan Ding, Yiyang Mao, Binsen Rong, Ning Zhu, Kai Guo

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Abstract

The NH4I-triggered formal [4 + 2] annulation of α,β-unsaturated ketoxime acetates with N-acetyl enamides has been developed. The current protocol employs electron-rich enamides as C2 synthons and enables the efficient and straightforward construction of polysubstituted pyridines in moderate to good yields based on metal-free systems. The reaction tolerates a wide range of functional groups and represents an alternate route toward the synthesis of pyridine derivatives.

Original languageEnglish
Pages (from-to)8157-8165
Number of pages9
JournalJournal of Organic Chemistry
Volume85
Issue number12
DOIs
StatePublished - 19 Jun 2020

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