N-Acylation of 4-alkylidene-β-lactams: unexpected results |
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| Authors: | Gianfranco CainelliDaria Giacomini Massimo GazzanoPaola Galletti Arianna Quintavalla |
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| Affiliation: | Department of Chemistry ‘G. Ciamician’, University of Bologna and ISOF (C.N.R.), Via Selmi 2, Bologna 40126, Italy |
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| Abstract: | This paper describes the different reactivity of E- and Z-4-alkylidene-β-lactams in acylation reactions under basic conditions. The E isomer is readily acylated, whereas the Z reacted sluggishly rearranging to the corresponding oxazin-6-one. The N-acylation of Z isomers was successfully obtained with oxalyl- or malonyl chlorides in benzene at reflux. |
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