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, Page 171-180 PDF (675.57 K) | ||||
| Document Type: Original Article | ||||
| DOI: 10.21608/ejchem.2018.4427.1393 | ||||
 View on SCiNiTO | ||||
| Authors | ||||
Mona E. Farhan  ; Mohammed G. Assy
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| 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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