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Paper | Regular issue | Vol 71, No. 12, 2007, pp.2617-2626
Published online, 14th August, 2007
DOI: 10.3987/COM-07-11129
Reaction of Hydrazide of (Tetrazol-5-yl)acetic Acid with Isothiocyanates and Antimicrobial Investigations of Newly-Obtained Compounds

Monika Wujec,* Urszula Kosikowska, Piotr Paneth, and Anna Malm

*Department of Organic Chemistry, Medical University, 6 Staszica Str., 20-081 Lublin, Poland

Abstract

In the reaction of hydrazide of (tetrazol-5-yl)acetic acid (1) with isothiocyanate the respective thiosemicarbazide derivatives 2 were obtained. Further cyclization with 2% NaOH led to the formation of 3-[(tetrazol-5-yl)-methyl]-4-substituted-1,2,4-triazoline-5-thione 3. The structures of all new products were confirmed by analytical and spectroscopic methods. Five compounds were screened for their in vitro activity against some species of aerobic bacteria and fungi. Derivatives of 1,2,4-triazoline-5-thione can exist in two major tautomeric forms; thiole and thione. We have established experimentally that all obtained compounds 3, were in the thione form. Geometry optimization of tautomeric forms of 3c and 3f was carried out.