Iron-catalyzed [4 + 2] annulation of α,β-unsaturated ketoxime acetates with enaminones toward functionalized pyridines

Jindian Duan; Gaochen Xu; Binsen Rong; Huan Yan; Sai Zhang; Qinghuan Wu; Ning Zhu; Kai Guo

doi:10.1016/j.gresc.2021.03.001

Iron-catalyzed [4 + 2] annulation of α,β-unsaturated ketoxime acetates with enaminones toward functionalized pyridines

Jindian Duan, Gaochen Xu, Binsen Rong, Huan Yan, Sai Zhang, Qinghuan Wu, Ning Zhu, Kai Guo

COLLEGE OF BIOTECHNOLOGY AND PHARMACEUTICAL ENGINEERING

Nanjing Tech University

Research output: Contribution to journal › Article › peer-review

31 Scopus citations

Abstract

The iron-catalyzed [4 + 2] annulation of α,β-unsaturated ketoxime acetates with enaminones has been developed, providing efficient access to highly substituted pyridines in moderate to good yields. Notable features of the present strategy include low-cost catalytic system, simple and mild reaction condition and wide substrate scope. Mechanistic studies reveal that FeCl₂ may directly serve as a Lewis acid to activate the α,β-unsaturated ketoxime acetates for the nucleophilic addition.

Original language	English
Pages (from-to)	237-240
Number of pages	4
Journal	Green Synthesis and Catalysis
Volume	2
Issue number	2
DOIs	https://doi.org/10.1016/j.gresc.2021.03.001
State	Published - May 2021

Keywords

Enaminones
Iron-catalyzed
Ketoxime acetates
Pyridines
[4 + 2] annulation

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title = "Iron-catalyzed [4 + 2] annulation of α,β-unsaturated ketoxime acetates with enaminones toward functionalized pyridines",

abstract = "The iron-catalyzed [4 + 2] annulation of α,β-unsaturated ketoxime acetates with enaminones has been developed, providing efficient access to highly substituted pyridines in moderate to good yields. Notable features of the present strategy include low-cost catalytic system, simple and mild reaction condition and wide substrate scope. Mechanistic studies reveal that FeCl2 may directly serve as a Lewis acid to activate the α,β-unsaturated ketoxime acetates for the nucleophilic addition.",

keywords = "Enaminones, Iron-catalyzed, Ketoxime acetates, Pyridines, [4 + 2] annulation",

author = "Jindian Duan and Gaochen Xu and Binsen Rong and Huan Yan and Sai Zhang and Qinghuan Wu and Ning Zhu and Kai Guo",

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T1 - Iron-catalyzed [4 + 2] annulation of α,β-unsaturated ketoxime acetates with enaminones toward functionalized pyridines

AU - Duan, Jindian

AU - Xu, Gaochen

AU - Rong, Binsen

AU - Yan, Huan

AU - Zhang, Sai

AU - Wu, Qinghuan

AU - Zhu, Ning

AU - Guo, Kai

PY - 2021/5

Y1 - 2021/5

N2 - The iron-catalyzed [4 + 2] annulation of α,β-unsaturated ketoxime acetates with enaminones has been developed, providing efficient access to highly substituted pyridines in moderate to good yields. Notable features of the present strategy include low-cost catalytic system, simple and mild reaction condition and wide substrate scope. Mechanistic studies reveal that FeCl2 may directly serve as a Lewis acid to activate the α,β-unsaturated ketoxime acetates for the nucleophilic addition.

AB - The iron-catalyzed [4 + 2] annulation of α,β-unsaturated ketoxime acetates with enaminones has been developed, providing efficient access to highly substituted pyridines in moderate to good yields. Notable features of the present strategy include low-cost catalytic system, simple and mild reaction condition and wide substrate scope. Mechanistic studies reveal that FeCl2 may directly serve as a Lewis acid to activate the α,β-unsaturated ketoxime acetates for the nucleophilic addition.

KW - Enaminones

KW - Iron-catalyzed

KW - Ketoxime acetates

KW - Pyridines

KW - [4 + 2] annulation

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DO - 10.1016/j.gresc.2021.03.001

M3 - 文章

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SN - 2666-5549

VL - 2

SP - 237

EP - 240

JO - Green Synthesis and Catalysis

JF - Green Synthesis and Catalysis

IS - 2

ER -

Iron-catalyzed [4 + 2] annulation of α,β-unsaturated ketoxime acetates with enaminones toward functionalized pyridines

Abstract

Keywords

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