Synlett

N-amino-N-methylmorpholinium salts: Highly active aziridination reagents for chalcones

…, DR Carbery, SG Lamont, AR Pape, R Wincewicz

Index: Armstrong, Alan; Carbery, David R.; Lamont, Scott G.; Pape, Andrew R.; Wincewicz, Richard Synlett, 2006 , # 15 p. 2504 - 2506

Full Text: HTML

Citation Number: 15

Abstract

We began by testing the Xu nitrate salt 1 (2 equiv) for aziridination of chalcone with alternative bases and solvents. Early studies showed that it was possible to use NaOH in MeCN, but the yield of aziridine was low (17% after 18 h). Therefore we prepared alternative hydrazinium nitrate salts by amination of several cyclic amines. While the hydrazinium salts derived from N-methylpyrrolidine and N-methylpiperidine gave comparable or lower yields of aziridine, we were delighted ...