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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 and Kai Guo*

*College of Biotechnology and Pharmaceutical Engineering, Nanjing Tech University, Nanjing 211816, China, Email: guoknjtech.edu.cn

J. Duan, L. Zhang, G. Xu, H. Chen, X. Ding, Y. Mao, B. Rong, N. Zhu, K. Guo, J. Org. Chem., 2020, 85, 8157-8165.

DOI: 10.1021/acs.joc.0c01081 (free Supporting Information)


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Abstract

The NH4I-triggered formal [4 + 2] annulation of α,β-unsaturated ketoxime acetates with N-acetyl enamides enables an efficient and straightforward construction of polysubstituted pyridines in good yields. This metal-free protocol employs electron-rich enamides as C2 synthons and tolerates a wide range of functional groups.

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Key Words

pyridines


ID: J42-Y2020