%0 Journal Article
%T Synthesis, Structure Elucidation and Reactivity of Novel Azetidinone-oxiranes
%A Antoli£¿
%A Snje£¿ana
%A Koji£¿-Prodi£¿
%A Biserka
%A Kova£¿evi£¿
%A Mi£¿e
%A Tomi£¿
%A Mirjana
%J -
%D 2002
%X Sa£¿etak Oxidation of 2,3-cis-2-sulfonamide-N-butenoate-azetidinone 3 and 2,3-trans-2-acetoxy-N-butenoate-azetidinone 6 led to the formation of azetidinone-oxiranes 5 and 7. Molecular structure of 5, including its absolute configuration, was unambiguously determined by X-ray structure analysis. Cleavage of the benzyl ester group using AlCl3 / anisole as well as H2Pd/C procedures failed. Instead, new methods for the removal of the substituent from the azetidinone nitrogen of compounds 5 and 7 were found. Azetidinone 8 was isolated in the reaction of azetidinone-oxiranes 5 with AlCl3/anisole. During hydrogenation of azetidinone-oxirane 5, afforded azetidinone p-hydroxy acid sodium salt 9, which was transformed into azetidinone 8 in acidic media. Compounds 5 and 7 gave the azetidinone-halohydrines 10 and 11 by the oxirane ring opening with HCl
%K azetidinone-N-butenoat
%K azetidinone-oxirane
%K azetidinone ¦Â-hydroxy acid
%K azetidinone-halohydrine
%K synthesis
%K X-ray structure analysis
%K antibacterial activity
%U https://hrcak.srce.hr/index.php?show=clanak&id_clanak_jezik=188259