Cu(II)-catalyzed cyclization of α-diazo-β-oxoamides with amines leading to pyrrol-3(2H)-ones

Zikun Wang; Xihe Bi; Peiqiu Liao; Xu Liu; Dewen Dong

doi:10.1039/C2CC38473F

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Cu(ii)-catalyzed cyclization of α-diazo-β-oxoamides with amines leading to pyrrol-3(2H)-ones†

Zikun Wang,^a Xihe Bi,*^bc Peiqiu Liao,^b Xu Liu^a and Dewen Dong*^ab

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* Corresponding authors

^a Changchun Institute of Applied Chemistry, Chinese Academy of Sciences, Changchun, China
E-mail: dwdong@ciac.jl.cn

^b Department of Chemistry, Northeast Normal University, Changchun, China
E-mail: bixh507@nenu.edu.cn

^c State Key Laboratory of Elemento-organic Chemistry, Tianjin 300071, China

Abstract

A novel Cu(II)-catalyzed cyclization of α-diazo-β-oxoamides with amines has been developed, constituting a straightforward method to construct pyrrol-3(2H)-one rings. The intramolecular hydrogen bonding effect in α-diazo-β-oxoamides plays an essential role in this reaction. A plausible reaction mechanism involving divergent generation and subsequent [2 + 3] cyclization of ketene and α-diazoimine intermediates was proposed.

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Article information

DOI: https://doi.org/10.1039/C2CC38473F
Article type: Communication
Submitted: 25 Nov 2012
Accepted: 18 Dec 2012
First published: 10 Jan 2013

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Chem. Commun., 2013,49, 1309-1311

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Cu(II)-catalyzed cyclization of α-diazo-β-oxoamides with amines leading to pyrrol-3(2H)-ones

Z. Wang, X. Bi, P. Liao, X. Liu and D. Dong, Chem. Commun., 2013, 49, 1309 DOI: 10.1039/C2CC38473F

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Chemical Communications

Cu(ii)-catalyzed cyclization of α-diazo-β-oxoamides with amines leading to pyrrol-3(2H)-ones†

Abstract

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Cu(II)-catalyzed cyclization of α-diazo-β-oxoamides with amines leading to pyrrol-3(2H)-ones

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