Synthesis, structure elucidation and reactivity of novel azetidinone-oxiranes

Tomić, Mirjana; Kovačević, Miće; Antolić, Snježana; Kojić-Prodić, Biserka (2002) Synthesis, structure elucidation and reactivity of novel azetidinone-oxiranes. Croatica Chemica Acta, 75 (1). pp. 211-224. ISSN 0011-1643

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Abstract

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.

Item Type:	Article
Uncontrolled Keywords:	azetidinone-N-butenoat; azetidinone-oxirane; azetidinone beta-hydroxy acid; azetidinone-halohydrine; synthesis; X-ray structure analysis; antibacterial activity;
Subjects:	NATURAL SCIENCES > Chemistry
Divisions:	Division of Physical Chemistry
Projects:	Project title Project leader Project code Project type Struktura i dinamika (bio)molekula Biserka Kojić-Prodić 0098036 MZOS
Depositing User:	Biserka Kojić-Prodić
Date Deposited:	19 Nov 2013 11:05
URI:	http://fulir.irb.hr/id/eprint/977

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