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HERO ID
7448300
Reference Type
Journal Article
Title
Novel spiroheterocycles by aziridination of alpha-methylene-gamma- and -delta-lactams
Author(s)
Loreto, MA; Migliorini, A; Tardella, PA; Gambacorta, A
Year
2007
Is Peer Reviewed?
Yes
Journal
European Journal of Organic Chemistry
ISSN:
1434-193X
EISSN:
1099-0690
Volume
2007
Issue
14
Page Numbers
2365-2371
Language
English
DOI
10.1002/ejoc.200601034
Web of Science Id
WOS:000246656700017
Abstract
New potentially bioactive α-spiroaziridino-γ- and -δ-lactams have been prepared by treatment of α-methylene-γ- and -δ-lactams with ethyl N-([(4-nitrophenyl)sulfonyl]oxy)-carbamate (NsONHCO2Et) in the presence of CaO. These compounds, through reductive aziridine ring opening, can be intermediates for the synthesis of α- and β-aminolactams, which are useful as conformational constraints in peptides. The above procedure has been successfully extended to one α-methyleneoxindole to obtain a new spirooxindole derivative, a potential precursor of natural alkaloids. © Wiley-VCH Verlag GmbH & Co. KGaA, 2007.
Keywords
aziridination; lactams; spiroheterocycles; ring opening; amino lactams
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