Copper-catalyzed [4+2] oxidative annulation of α,β-unsaturated ketoxime acetates with ethyl trifluoropyruvate

Huan Yan; Gaochen Xu; Meng Gu; Sai Zhang; Qinghuan Wu; Jingjing Meng; Ning Zhu; Zheng Fang; Jindian Duan; Kai Guo

doi:10.1039/d2cc01573k

Copper-catalyzed [4+2] oxidative annulation of α,β-unsaturated ketoxime acetates with ethyl trifluoropyruvate

Huan Yan, Gaochen Xu, Meng Gu, Sai Zhang, Qinghuan Wu, Jingjing Meng, Ning Zhu, Zheng Fang, Jindian Duan, Kai Guo

COLLEGE OF BIOTECHNOLOGY AND PHARMACEUTICAL ENGINEERING

Nanjing Tech University

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

11 Scopus citations

Abstract

A novel route for tandem C-N/C-O formation via copper-catalyzed [4+2] oxidative annulation of α,β-unsaturated ketoxime acetates with ethyl trifluoropyruvate to synthesize valuable trifluoromethyl-containing 2H-1,3-oxazines in moderate to good yields is developed. This procedure represents the first [4+2] oxidative annulation of oxime derivatives with activated C = O bonds and provides an alternative route towards functionalized 2H-1,3-oxazines.

Original language	English
Pages (from-to)	6757-6760
Number of pages	4
Journal	Chemical Communications
Volume	58
Issue number	47
DOIs	https://doi.org/10.1039/d2cc01573k
State	Published - 18 May 2022

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title = "Copper-catalyzed [4+2] oxidative annulation of α,β-unsaturated ketoxime acetates with ethyl trifluoropyruvate",

abstract = "A novel route for tandem C-N/C-O formation via copper-catalyzed [4+2] oxidative annulation of α,β-unsaturated ketoxime acetates with ethyl trifluoropyruvate to synthesize valuable trifluoromethyl-containing 2H-1,3-oxazines in moderate to good yields is developed. This procedure represents the first [4+2] oxidative annulation of oxime derivatives with activated C = O bonds and provides an alternative route towards functionalized 2H-1,3-oxazines.",

author = "Huan Yan and Gaochen Xu and Meng Gu and Sai Zhang and Qinghuan Wu and Jingjing Meng and Ning Zhu and Zheng Fang and Jindian Duan and Kai Guo",

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doi = "10.1039/d2cc01573k",

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T1 - Copper-catalyzed [4+2] oxidative annulation of α,β-unsaturated ketoxime acetates with ethyl trifluoropyruvate

AU - Yan, Huan

AU - Xu, Gaochen

AU - Gu, Meng

AU - Zhang, Sai

AU - Wu, Qinghuan

AU - Meng, Jingjing

AU - Zhu, Ning

AU - Fang, Zheng

AU - Duan, Jindian

AU - Guo, Kai

PY - 2022/5/18

Y1 - 2022/5/18

N2 - A novel route for tandem C-N/C-O formation via copper-catalyzed [4+2] oxidative annulation of α,β-unsaturated ketoxime acetates with ethyl trifluoropyruvate to synthesize valuable trifluoromethyl-containing 2H-1,3-oxazines in moderate to good yields is developed. This procedure represents the first [4+2] oxidative annulation of oxime derivatives with activated C = O bonds and provides an alternative route towards functionalized 2H-1,3-oxazines.

AB - A novel route for tandem C-N/C-O formation via copper-catalyzed [4+2] oxidative annulation of α,β-unsaturated ketoxime acetates with ethyl trifluoropyruvate to synthesize valuable trifluoromethyl-containing 2H-1,3-oxazines in moderate to good yields is developed. This procedure represents the first [4+2] oxidative annulation of oxime derivatives with activated C = O bonds and provides an alternative route towards functionalized 2H-1,3-oxazines.

UR - http://www.scopus.com/inward/record.url?scp=85131129643&partnerID=8YFLogxK

U2 - 10.1039/d2cc01573k

DO - 10.1039/d2cc01573k

M3 - 文章

AN - SCOPUS:85131129643

SN - 1359-7345

VL - 58

SP - 6757

EP - 6760

JO - Chemical Communications

JF - Chemical Communications

IS - 47

ER -

Copper-catalyzed [4+2] oxidative annulation of α,β-unsaturated ketoxime acetates with ethyl trifluoropyruvate

Abstract

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