Farhan, M., Assy, M. (2019). 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, 62(2), 171-180. doi: 10.21608/ejchem.2018.4427.1393
Mona E. Farhan; Mohammed G. Assy. "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, 62, 2, 2019, 171-180. doi: 10.21608/ejchem.2018.4427.1393
Farhan, M., Assy, M. (2019). '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, 62(2), pp. 171-180. doi: 10.21608/ejchem.2018.4427.1393
Farhan, M., Assy, M. 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, 2019; 62(2): 171-180. doi: 10.21608/ejchem.2018.4427.1393
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
Department of Chemistry, Faculty of Science, Zagazig University, Egypt.
Receive Date: 12 July 2018,
Revise Date: 19 August 2018,
Accept Date: 03 September 2018
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.
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