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

Document Type : Original Article

Authors

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.

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