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Issue 13, 2013
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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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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.

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

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Supplementary files

Article information


Submitted
25 Nov 2012
Accepted
18 Dec 2012
First published
10 Jan 2013

Chem. Commun., 2013,49, 1309-1311
Article type
Communication

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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