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http://dx.doi.org/10.5012/jkcs.2010.54.4.414

Antimicrobial Assessment of Some Heterocyclic Compounds Utilizing Ethyl 1-Aminotetrazole-5-carboxylate  

Taha, Mamdouh A. M. (Chemistry Department, Faculty of Science, Faiyoum University)
El-Badry, Susan M. (Physics and Chemistry Department, Faculty of Education, Alexandria University)
Publication Information
Journal of the Korean Chemical Society / v.54, no.4, 2010 , pp. 414-418 More about this Journal
Abstract
Ethyl 1-aminotetrazole-5-carboxylate (1) reacted with hydrazine hydrate to give the corresponding aminohydrazide 2. Cyclization of 2 by carbon disulfide yielded 1,3,4-oxadiazole-5-thiol structure 3. Reaction of 3 with either chloroacetone or ethyl chloroacetate furnished S-acyl 1,3,4-oxadiazole derivatives 4 and 5, respectively. Also compound 3 reacted with hydrazine hydrate afforded 4-amino-1,2,4-triazole-5-thiol derivative 6. 6-Methyl-1,3,4-triazolo[3,4-b]-1,3,4-thiadiazole structure 7 was synthesized by reaction of aminothiol 6 with glacial acetic acid. Diazotization of 1 with sodium nitrite in presence of hydrochloric acid yielding the diazonium salt which on treating with hippuric acid, oxazolone derivative 8 was obtained. Furthermore, tetrazolo[5,1-f]-1,2,4-triazine 9 was constructed via cyclization of aminoester 1 with formamide. Compound 9 reacted with carbon disulfide to furnish 8-thione derivative 10 which reacting with chloroacetone, ethyl chloroacetate, and hydrazine hydrate, the corresponding chemical structures 11, 12, and 13 were synthesized. 1,2,4-Triazolo[4,3-d]tetrazolo[5,1-f]-1,2,4-triazines 14 and 15 were resulted by treating of compound 13 with triethyl orthoformate, and glacial acetic acid, respectively. The structures of the newly synthesized products were elucidated according to elemental analyses and spectroscopic evidences. Some of the representative members of the prepared compounds were screened for antimicrobial activity.
Keywords
1-Aminotetrazole-5-carboxylate; 1,3,4-Oxadiazoles; 1,2,4-Triazole; Oxazole; Fused heterocyclic ring systems; Antimicrobial activity;
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