Heterocyclization of Isoniazid: Synthesis and Antimicrobial Activity of Some New Pyrimidine, 1, 3-Thiazole, 1, 2, 4-Thiadiazole, and 1, 2, 4-Triazole Derivatives Derived from Isoniazid | ||
| Egyptian Journal of Chemistry | ||
| Article 1, Volume 62, Issue 2, February 2019, Pages 171-180 PDF (675.57 K) | ||
| Document Type: Original Article | ||
| DOI: 10.21608/ejchem.2018.4427.1393 | ||
| Authors | ||
| Mona E. Farhan* ; Mohammed G. Assy | ||
| Department of Chemistry, Faculty of Science, Zagazig University, Egypt. | ||
| Abstract | ||
| The reaction of isonicotinic hydrazide (1) (isoniazid) with cinnamoyl isothiocyanate (2) afforded cinnamoyl thiosemicarbazide derivative 3. Treatment of 3 with lead acetate in acetic acid, sodium ethoxide, sulphuric acid, chloroacetylchloride and sodium hypochlorite and sodium hydroxide gave the corresponding dihydropyrimidine 4, triazolethiazine 5, 1,3,4-thiadiazole 6, 1,3-thiazole 7 and 1,2,4-thiadiazole 8, respectively. The reactivity of isoniazid 1 towards ammonium thiocyanate, cyclohexanone and acetophenone to give 1,2,4-triazole thione 10, hydrazones 9 and 12 was studied. Treatment of hydrazones 9 and 12 with carbon disulfide and aryl isothiocyanates gave 1,3,4-thiadiazolidine 11 and 1,2,4-triazole thione derivatives 13a, b. The antimicrobial activity of these new compounds has been evaluated against 6 microbial strains. Some of the newly synthesized compounds showed a moderate activity. | ||
| Keywords | ||
| isonicotinichydrazide; triazolothiazine; thiadiazole; triazolethione; dihydropyrimidine; thiazole; antimicrobial activity | ||
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