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Synfacts 2008(3): 0247-0247  
DOI: 10.1055/s-2008-1042752
Synthesis of Heterocycles
© Georg Thieme Verlag Stuttgart · New York

Synthesis of Imidazolines from N-Imidoylaziridines

Contributor(s): Victor Snieckus, Wei Gan
Y. Han, Y.-X. Xie, L.-B. Zhao, L.-J. Fan, Y.-M. Liang*
Lanzhou University and Lanzhou Institute of Chemical Physics, P. R. of China
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Publication History

Publication Date:
21 February 2008 (online)

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Significance

Reported is a two-step synthesis of 2,4,5-substituted imidazolines via N-imidoylaziridines A by a three-component reaction between terminal acetylenes under copper-catalytic conditions, N-unsubstituted aziridines, and sulfonyl azides. In the study of the synthesis of A, it was found that both aromatic and aliphatic alkynes undergo the observed reaction. However, no product was observed when substituted terminal alkynes or an electron-poor aziridine (Ar1 = 4-O2NC6H4 ) were involved. In case of the second step, only trans isomers of imidazolines were formed at room temperature. However, a mixture of trans and cis (3:1) imidazolines was observed under reflux conditions.