Synthesis of N-substituted azetidin-3-ones

Authors
Marchand, AP Devasagayaraj, A
Citation
Ap. Marchand et A. Devasagayaraj, Synthesis of N-substituted azetidin-3-ones, SYN COMMUN, 29(5), 1999, pp. 885-890
Citations number
17
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
SYNTHETIC COMMUNICATIONS
ISSN journal
00397911 → ACNP
Volume
29
Issue
5
Year of publication
1999
Pages
885 - 890
Database
ISI
SICI code
0039-7911(1999)29:5<885:SONA>2.0.ZU;2-N
Abstract
Addition of RC(O)CI (R = Oft, Me, or Ph) across the highly strained N-C(3) sigma-bond in 3-bromomethyl-1-azabicyclo[1.1.0]butane (1) afforded the corr esponding N-acyl-3-bromomethyl-3-chloroazetidines (2a-2c, respectively). Su bsequent zinc promoted eliminative dehalogenation of 2a-2c produced the cor responding N-acyl-3-methyleneazetidines (3a-3c, respectively). Finally, ozo nolysis of 3a-3c afforded the corresopnding N-acylazetidin-3-ones (4a-4c, r espectively).