Unprecedented carbon-carbon bond cleavage in nucleophilic aziridine ring opening reaction, efficient ring transformation of aziridines to imidazolidin-4-ones.
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 Cs(2)CO(3), 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.
Wang
Jin-Yuan
JY
Beijing National Laboratory for Molecular Sciences, Laboratory of Chemical Biology, Institute of Chemistry, Chinese Academy of Sciences, Beijing, 100190, China.
Hu
Yuan
Y
Wang
De-Xian
DX
Pan
Jie
J
Huang
Zhi-Tang
ZT
Wang
Mei-Xiang
MX