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Novel Spiroheterocycles by Aziridination of α‐Methylene‐γ‐ and ‐δ‐lactams
Author(s) -
Loreto M. Antonietta,
Migliorini Antonella,
Tardella P. Antonio,
Gambacorta Augusto
Publication year - 2007
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200601034
Subject(s) - chemistry , aziridine , methylene , ring (chemistry) , carbamate , derivative (finance) , staudinger reaction , stereochemistry , sulfonyl , combinatorial chemistry , lactam , organic chemistry , alkyl , financial economics , economics
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 (NsONHCO 2 Et) 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, 69451 Weinheim, Germany, 2007)