Synthesis and characterization of new 5-(4-chlorobenzyl)-1,3,4-oxadiazol-2-amine derivatives | ||||
| Egyptian Journal of Chemistry | ||||
| Article 19, Volume 63, Issue 2, February 2020, Page 573-578 PDF (1.29 MB) | ||||
| Document Type: Original Article | ||||
| DOI: 10.21608/ejchem.2020.20671.2239 | ||||
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| Author | ||||
Eid Eissa Salama  
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| Chemistry Department- Faculty of Science- Suez Canal University | ||||
| Abstract | ||||
| Due to the biological significance of 1,3,4-oxadiazoles this work is concerned with the synthesis and reactions of new 5-(4-chlorobenzyl)-1,3,4-oxadiazol-2-amine 1. The parent oxadiazole 1 was obtained from reaction of 4-chlorophenylacetic acid with semicarbazide in the presence of phosphorus oxychloride followed by addition of potassium hydroxide. Acylation of amino oxadiazoles 1 with acid chlorides such as acetyl chloride, benzoyl chloride, 3-nitrobenzoyl chloride, 4-methoxybenzoyl chloride, 4-tert-butylbenzoyl chloride and chloroacetyl chloride in the presence of triethylamine yielded the acylated compounds 2-7. Reaction of phenyl isocyanate and 3-chlorophenyl isocyanate with oxadiazole 1 afforded the urea derivatives 8 and 9. Cyclization of acetamide 7 by reaction with ammonium thiocyanate gave thiazolidinone 10. Coupling of chloroacetamide 7 with mercapto derivatives in the presence of diisopropylethylamine give oxadiazole derivatives 11-13. New compounds were obtained in a good yield and elucidation was done using mass spectrometry, 1H-NMR and 13C-NMR. | ||||
| Keywords | ||||
| Phenylacetic acid; 1; 3; 4-oxadiazoles; acid chloride; thiazolidinone; coupling | ||||
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