Copper(I)-Catalyzed [4+2] Oxidative Annulation of α,β-Unsaturated Ketoxime Acetates with Cyclopropanols toward Functional Pyridines

Qinghuan Wu; Gaochen Xu; Yuguang Li; Lei Shen; Zheng Fang; Jindian Duan; Kai Guo

doi:10.1002/adsc.202301069

Copper(I)-Catalyzed [4+2] Oxidative Annulation of α,β-Unsaturated Ketoxime Acetates with Cyclopropanols toward Functional Pyridines

Qinghuan Wu, Gaochen Xu, Yuguang Li, Lei Shen, Zheng Fang, Jindian Duan, Kai Guo

COLLEGE OF BIOTECHNOLOGY AND PHARMACEUTICAL ENGINEERING

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

3 Scopus citations

Abstract

A Cu(I)-catalyzed [4+2] oxidative annulation of α,β-unsaturated ketoxime acetates with cyclopropanols has been developed for the synthesis of 2,4,5-trisubstituted pyridines in 28–76% yields. This method employs cyclopropanols as C2 synthons and features various functional group compatibility and gram-scale synthesis. In addition, a plausible reaction pathway was proposed based on the mechanism studies.

Original language	English
Pages (from-to)	4310-4316
Number of pages	7
Journal	Advanced Synthesis and Catalysis
Volume	365
Issue number	23
DOIs	https://doi.org/10.1002/adsc.202301069
State	Published - 5 Dec 2023

Keywords

TEMPO
cyclopropanols
oxidative annulation
pyridines
α,β-unsaturated ketoximes

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title = "Copper(I)-Catalyzed [4+2] Oxidative Annulation of α,β-Unsaturated Ketoxime Acetates with Cyclopropanols toward Functional Pyridines",

abstract = "A Cu(I)-catalyzed [4+2] oxidative annulation of α,β-unsaturated ketoxime acetates with cyclopropanols has been developed for the synthesis of 2,4,5-trisubstituted pyridines in 28–76% yields. This method employs cyclopropanols as C2 synthons and features various functional group compatibility and gram-scale synthesis. In addition, a plausible reaction pathway was proposed based on the mechanism studies.",

keywords = "TEMPO, cyclopropanols, oxidative annulation, pyridines, α,β-unsaturated ketoximes",

author = "Qinghuan Wu and Gaochen Xu and Yuguang Li and Lei Shen and Zheng Fang and Jindian Duan and Kai Guo",

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doi = "10.1002/adsc.202301069",

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T1 - Copper(I)-Catalyzed [4+2] Oxidative Annulation of α,β-Unsaturated Ketoxime Acetates with Cyclopropanols toward Functional Pyridines

AU - Wu, Qinghuan

AU - Xu, Gaochen

AU - Li, Yuguang

AU - Shen, Lei

AU - Fang, Zheng

AU - Duan, Jindian

AU - Guo, Kai

PY - 2023/12/5

Y1 - 2023/12/5

N2 - A Cu(I)-catalyzed [4+2] oxidative annulation of α,β-unsaturated ketoxime acetates with cyclopropanols has been developed for the synthesis of 2,4,5-trisubstituted pyridines in 28–76% yields. This method employs cyclopropanols as C2 synthons and features various functional group compatibility and gram-scale synthesis. In addition, a plausible reaction pathway was proposed based on the mechanism studies.

AB - A Cu(I)-catalyzed [4+2] oxidative annulation of α,β-unsaturated ketoxime acetates with cyclopropanols has been developed for the synthesis of 2,4,5-trisubstituted pyridines in 28–76% yields. This method employs cyclopropanols as C2 synthons and features various functional group compatibility and gram-scale synthesis. In addition, a plausible reaction pathway was proposed based on the mechanism studies.

KW - TEMPO

KW - cyclopropanols

KW - oxidative annulation

KW - pyridines

KW - α,β-unsaturated ketoximes

UR - http://www.scopus.com/inward/record.url?scp=85176766309&partnerID=8YFLogxK

U2 - 10.1002/adsc.202301069

DO - 10.1002/adsc.202301069

M3 - 文章

AN - SCOPUS:85176766309

SN - 1615-4150

VL - 365

SP - 4310

EP - 4316

JO - Advanced Synthesis and Catalysis

JF - Advanced Synthesis and Catalysis

IS - 23

ER -

Copper(I)-Catalyzed [4+2] Oxidative Annulation of α,β-Unsaturated Ketoxime Acetates with Cyclopropanols toward Functional Pyridines

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Keywords

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