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Issue 4, 2009
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Unprecedented carbon–carbon bond cleavage in nucleophilic aziridine ring opening reaction, efficient ring transformation of aziridines to imidazolidin-4-ones

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Abstract

N-Styryl-3-aryl-1-methylaziridine-2-carboxamides, which were readily obtained from the cross coupling reaction between 3-aryl-1-methylaziridine-2-carboxamides and 1-aryl-2-bromoethenes catalyzed by CuI/N,N-dimethylglycine in the presence of Cs2CO3, underwent a base-mediated intramolecular nucleophilic aziridine ring opening reaction effectively via the carbon–carbon bond cleavage of aziridine to afford the ring expanded imidazolidin-4-one products in good yields.

Graphical abstract: Unprecedented carbon–carbon bond cleavage in nucleophilic aziridine ring opening reaction, efficient ring transformation of aziridines to imidazolidin-4-ones

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Article information


Submitted
12 Sep 2008
Accepted
20 Oct 2008
First published
18 Nov 2008

Chem. Commun., 2009, 422-424
Article type
Communication

Unprecedented carbon–carbon bond cleavage in nucleophilic aziridine ring opening reaction, efficient ring transformation of aziridines to imidazolidin-4-ones

J. Wang, Y. Hu, D. Wang, J. Pan, Z. Huang and M. Wang, Chem. Commun., 2009, 422
DOI: 10.1039/B816007D

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