TAILIEUCHUNG - Synthesis of some new[(5-aryloxymethyl 1,3,4-oxadiazol 2 yl)sulfanyl]acetamide compounds

5-(4-Bromophenyloxymethyl)-1,3,4-oxadiazol-2-thiole (3a) and 5-(4 -methylphenyloxymethyl)-1,3,4-oxadiazol-2-thiole (3b) were synthesized starting from 4-bromophenol and 4-methylphenol (p-crezol), respectively. The 5-aryl- -oxymethyl-1,3,4-oxadiazole-2-thiole (3a, b) were treated with N-aryl-2-chloro- -acetamides to give six corresponding new N-aryl-[(5-aryloxymethyl-1,3,4- -oxadiazol-2-yl)sulfanyl]acetamides (4a1-3, 4b1-3). | JOURNAL OF SCIENCE OF HNUE Chemical and Biological Sci. 2014 Vol. 59 No. 9 pp. 30-36 This paper is available online at http SYNTHESIS OF SOME NEW 5-ARYLOXYMETHYL-1 3 4- OXADIAZOL-2-YL SULFANYL ACETAMIDE COMPOUNDS Nguyen Tien Cong Ho Xuan Dau and Bui Thi Luong Faculty of Chemistry Ho Chi Minh University of Education Abstract. 5- 4-Bromophenyloxymethyl -1 3 4-oxadiazol-2-thiole 3a and 5- 4 -methylphenyloxymethyl -1 3 4-oxadiazol-2-thiole 3b were synthesized starting from 4-bromophenol and 4-methylphenol p-crezol respectively. The 5-aryl- -oxymethyl-1 3 4-oxadiazole-2-thiole 3a b were treated with N-aryl-2-chloro- -acetamides to give six corresponding new N-aryl- 5-aryloxymethyl-1 3 4- -oxadiazol-2-yl sulfanyl acetamides 4a1-3 4b1-3 . The structures of the compounds were confirmed by IR 1 H-NMR and MS spectral data. At concentrations up to the acetamide compounds 4a1-3 4b1-3 exhibited weak antibacterial capacity against Escherichia coli and Bacillus subtilis. Keywords 5- 4-Bromophenyloxymethyl -1 3 4-oxadiazol-2-thiole 5- 4-methyl- -phenyloxymethyl -1 3 4-oxadiazol-2-thiole tautomer 1 3 4-oxadiazol-2-ylsulfa- -nyl acetamide antimicrobial activity. 1. Introduction Of the five-membered nitrogen heterocycles 1 3 4-oxadiazoles have received attention due to their wide range of biological activities. Compounds containing a 1 3 4-oxadiazole nucleus possess antibacterial fungicidal insecticidal herbicidal anti-inflammatory antiviral and antitumour characteristics 3 11 14 . Transformation of the 5-alkyl aryl-1 3 4-oxadiazol-2-thiol compounds to thioether derivatives lead molecules for the design of potential bioactive agents. In this way many 5-alkyl aryl-1 3 4-oxadiazol-2-yl sulfanyl acetamides were synthesized and evaluated for biological activities 2 8-10 12 13 . Thus we have designed and synthesized a series of aryloxymethyl-1 3 4-oxadiazol-2-yl sulfanyl acetamides and tested them for antibacterial activity. Received August 13 2014. Accepted October

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