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Malaysian Journal of Chemistry, 2017, Vol. 19(2), 118 – 123

One-pot Synthesis of 3,3,7,7-Tetramethyl- tetrahydro-[1,2,4]
triazolo[1,2-a][1,2,4]triazole- 1,5-dithione and its Biological Activities

Syadza Firdausiah1,3, Siti Aishah Hasbullah1, Chew Shing Hii2, Nazlina Ibrahim2
and Bohari M. Yamin1*
1School of Chemical Sciences and Food Technology, Faculty of Science and Technology, 43600 UKM Bangi, Selangor D.E. Malaysia
2School of Bioscience and Biotechnology, Faculty of Science and Technology,
43600 UKM Bangi, Selangor D.E. Malaysia
3Chemistry Department, Faculty of Mathematics and Natural Science,
Hasanuddin University, Indonesia

*Corresponding author: (e-mail: This email address is being protected from spambots. You need JavaScript enabled to view it.) 

Received: January 2016; Accepted: April 2017

ABSTRACT

3,3,7,7-Tetramethyl-tetrahydro-[1,2,4]triazolo[1,2-a][1,2,4]triazole-1,5-dithione 1 has been synthesized from 2-chloropropionyl chloride ammonium thiocyanate, and hydrazine in 96% yield. Criss-cross cycloaddition involving aldazine produced from the acetone-hydrazine reaction was proposed for the mechanism. The structure was confirmed by micro-elemental analysis, FTIR, 1H and 13C NMR spectroscopy and ESI mass spectrometry. Compound  1 crystallized in monoclinic crystal system with P21/c space group. Antibacterial screening against Staphylococcus epidermidis, Staphylococcus aureus, Bacillus subtilis, Enterococcus faecalis, and  Gram-negative bacteria: Enterobacter aerogenes, Klebsiella pneumoniae, Proteus vulgaris, Escherichia coli, and Pseudomonas aeruginosa were conducted. The highest activity was against S. epidermidis (MIC = 1.563 mg/ml and MBC = 1.563 mg/ml) and Escherichia coli (MIC = 1.563 mg/ml and MBC = 1.563 mg/ml) thus exhibiting a moderate antibacterial activity.

Key words: Antibacterial activity; Criss-cross cycloaddition; X-ray crystal structure; triazole compound 

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