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-nitrobenzene)sulphonyl]oxy}carbamate (NsONHCO2Et), in the presence of CaO. These compounds, through reductive aziridine ring opening, can be intermediates for the synthesis of α- or β-amino lactams, useful as conformational constraints in peptides. The above procedure has been successfully extended to one α-methylene-oxindole to obtain a new spirooxindole derivative, potential precursor of natural alkaloids.

M. A., L., A., M., P. A., T., Gambacorta, A. (2007). Novel Spiroheterocycles by Aziridination of α-Methylene-γ- and δ-Lactams. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 14, 2365-2371 [10.1002/ejoc.200601034].

Novel Spiroheterocycles by Aziridination of α-Methylene-γ- and δ-Lactams

GAMBACORTA, Augusto
2007-01-01

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-nitrobenzene)sulphonyl]oxy}carbamate (NsONHCO2Et), in the presence of CaO. These compounds, through reductive aziridine ring opening, can be intermediates for the synthesis of α- or β-amino lactams, useful as conformational constraints in peptides. The above procedure has been successfully extended to one α-methylene-oxindole to obtain a new spirooxindole derivative, potential precursor of natural alkaloids.
2007
M. A., L., A., M., P. A., T., Gambacorta, A. (2007). Novel Spiroheterocycles by Aziridination of α-Methylene-γ- and δ-Lactams. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 14, 2365-2371 [10.1002/ejoc.200601034].
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/11590/120946
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