New potentially bioactive ?-spiroaziridino-?- and -?-lactams have been prepared by treatment of ?-methylene-?- and -?- 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 ?- and ?-aminolactams,which are useful as conformational constraints in peptides. The above procedure has been successfully extended to one ?-methyleneoxindole to obtain a new spirooxindole derivative, a potential precursor of natural alkaloids.
Novel Spiroheterocycles by Aziridination of α-Methylene-γ- and δ-Lactams / Loreto, Maria Antonietta; Migliorini, Antonella; A., Gambacorta; Tardella, Paolo Antonio. - In: EUROPEAN JOURNAL OF ORGANIC CHEMISTRY. - ISSN 1434-193X. - STAMPA. - issue 14(2007), pp. 2365-2371. [10.1002/ejoc.200601034]
Novel Spiroheterocycles by Aziridination of α-Methylene-γ- and δ-Lactams
LORETO, Maria Antonietta;MIGLIORINI, Antonella;TARDELLA, Paolo Antonio
2007
Abstract
New potentially bioactive ?-spiroaziridino-?- and -?-lactams have been prepared by treatment of ?-methylene-?- and -?- 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 ?- and ?-aminolactams,which are useful as conformational constraints in peptides. The above procedure has been successfully extended to one ?-methyleneoxindole to obtain a new spirooxindole derivative, a potential precursor of natural alkaloids.I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.
