Synthesis and antibacterial activity of some new 1,3,4-oxadiazole and 1,3,4-thiadiazole derivatives

Jumat Salimon, Nadia Salih, Ayad Hameed, Hiba Ibraheem, Emad Yousif

Research output: Contribution to journalArticle

33 Citations (Scopus)

Abstract

In the present study, a new 1,3,4-oxadiazole and 1,3,4-thiadiazole derivatives were synthesized. Benzol hydrazine (2) was prepared by the hydrazinolysis of methyl benzoate (1) with hydrazine hydrate in abs. ethanol. Condensation of (2) with chloroacetic acid in phosphoruse oxychloride results in the formation of 2-phenyl-5-chloromethyl-1,3,4-oxadiazole (3), which on reaction with 2,5-dimercapto-1,3,4-thiadiazole in pyridine affords 2,5-di-[5-phenyl-1,3,4-oxadiazole-2-thiomethyl]-1,3,4-thiadiazole (5). Furthermore, refluxing of 2,5-dimercapto-1,3,4-thiadizole (4) with chloroacetic acid yield 2,5-(dithioacetic acid)-1,3,4-thidiazole (6). Reaction of (6) with thiosemicarbazide in phosphoruse oxychloride gave 2,5-di-[5-amino-1,3,4-thiadiazole-2-thiomethyl]-1,3,4-thiadiazole (7). The newly synthesized compounds were characterized by CHNS elemental analysis, IR and NMR spectral data. The newly synthesized compounds werescreened for their in vitro antibacterial activity. The prepared compounds manifested promising biological activity.

Original languageEnglish
Pages (from-to)866-870
Number of pages5
JournalJournal of Applied Sciences Research
Volume6
Issue number7
Publication statusPublished - Jul 2010

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hydrazine
2-amino-1,3,4-thiadiazole
Derivatives
Bioactivity
Benzene
Condensation
Ethanol
Nuclear magnetic resonance
Acids
Chemical analysis
1,3,4-thiadiazole
1,3,4-oxadiazole
chloroacetic acid

Keywords

  • 1,3,4-oxadiazole
  • 1,3,4-thiadiazole
  • Antibacterial activity
  • Nitrogen heterocycles
  • Spectroscopic study

ASJC Scopus subject areas

  • General

Cite this

Synthesis and antibacterial activity of some new 1,3,4-oxadiazole and 1,3,4-thiadiazole derivatives. / Salimon, Jumat; Salih, Nadia; Hameed, Ayad; Ibraheem, Hiba; Yousif, Emad.

In: Journal of Applied Sciences Research, Vol. 6, No. 7, 07.2010, p. 866-870.

Research output: Contribution to journalArticle

Salimon, Jumat ; Salih, Nadia ; Hameed, Ayad ; Ibraheem, Hiba ; Yousif, Emad. / Synthesis and antibacterial activity of some new 1,3,4-oxadiazole and 1,3,4-thiadiazole derivatives. In: Journal of Applied Sciences Research. 2010 ; Vol. 6, No. 7. pp. 866-870.
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N2 - In the present study, a new 1,3,4-oxadiazole and 1,3,4-thiadiazole derivatives were synthesized. Benzol hydrazine (2) was prepared by the hydrazinolysis of methyl benzoate (1) with hydrazine hydrate in abs. ethanol. Condensation of (2) with chloroacetic acid in phosphoruse oxychloride results in the formation of 2-phenyl-5-chloromethyl-1,3,4-oxadiazole (3), which on reaction with 2,5-dimercapto-1,3,4-thiadiazole in pyridine affords 2,5-di-[5-phenyl-1,3,4-oxadiazole-2-thiomethyl]-1,3,4-thiadiazole (5). Furthermore, refluxing of 2,5-dimercapto-1,3,4-thiadizole (4) with chloroacetic acid yield 2,5-(dithioacetic acid)-1,3,4-thidiazole (6). Reaction of (6) with thiosemicarbazide in phosphoruse oxychloride gave 2,5-di-[5-amino-1,3,4-thiadiazole-2-thiomethyl]-1,3,4-thiadiazole (7). The newly synthesized compounds were characterized by CHNS elemental analysis, IR and NMR spectral data. The newly synthesized compounds werescreened for their in vitro antibacterial activity. The prepared compounds manifested promising biological activity.

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