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Synthesis, Structure Elucidation and Reactivity of Novel Azetidinone-oxiranes

Mirjana Tomić ; PLIVA d.d. Research and Development, Prilaz baruna Filipovića 25, 10 000 Zagreb, Croatia
Miče Kovačević ; PLIVA d.d. Research and Development, Prilaz baruna Filipovića 25, 10 000 Zagreb, Croatia
Snježana Antolić ; Institute Rudjer Bošković, P.O. Box 180, 10 002 Zagreb, Croatia
Biserka Kojić-Prodić ; Institute Rudjer Bošković, P.O. Box 180, 10 002 Zagreb, Croatia

Sažetak

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.

Ključne riječi

azetidinone-N-butenoat; azetidinone-oxirane; azetidinone β-hydroxy acid; azetidinone-halohydrine; synthesis; X-ray structure analysis; antibacterial activity

Hrčak ID:

127497

URI

https://hrcak.srce.hr/127497

Datum izdavanja:

4.2.2002.

Posjeta: 788 *