Subscribe to RSS
Please copy the URL and add it into your RSS Feed Reader.
https://www.thieme-connect.de/rss/thieme/en/10.1055-s-00000131.xml
Synfacts 2008(3): 0247-0247
DOI: 10.1055/s-2008-1042752
DOI: 10.1055/s-2008-1042752
Synthesis of Heterocycles
© Georg Thieme Verlag Stuttgart · New York
Synthesis of Imidazolines from N-Imidoylaziridines
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
Further Information
Publication History
Publication Date:
21 February 2008 (online)
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.