Abstract
Acetic acid hydrazides containing 1,2,4-triazol-3-one ring (4a-d) were synthesized by the reaction of compounds 2a-k with hydrazine hydrate. (5-Mercapto-1,3,4-oxadiazol-2-yl)methyl- 2,4-dihydro-3H-1,2,4-triazol-3-one derivatives (5a-d) were obtained from the reaction of compounds 4a-d with carbon disulfide in the presence of KOH. The treatment of compounds 5a- d with hydrazine hydrate led to the conversion of 1,3,4-oxadiazole ring to amino-1,2,4-triazole ring in compounds 6a-d. A second method involving the reaction of compounds 7a-d with thiocarbohydrazide also gave the same products, 6a-d. The condensation of compounds 6a-d
Highlights
The therapeutic effects of 1,2,4-triazole and 1,2,4-triazol-3-one containing compounds have been well studied for a number of pathological conditions including inflammation, cancer, pain, tuberculosis or hypertension
There are not many triazoles fused to thiadiazines or thiadiazoles, a number of them are incorporated into a wide variety of therapeutically important compounds possessing a broad spectrum of biological activities
The NH proton at position 1 of 2,4-dihydro-3H-1,2,4-triazol-3-one ring is adequately acidic for further reactions and various compounds having biological activity were synthesized via this NH substitution in our laboratories
Summary
The therapeutic effects of 1,2,4-triazole and 1,2,4-triazol-3-one containing compounds have been well studied for a number of pathological conditions including inflammation, cancer, pain, tuberculosis or hypertension.1-9 In addition, it was reported that 1,3,4-thiadiazoles exhibit various biological activities possibly due to the presence of the =N-C-S moiety.10 synthesis of triazoles fused to another heterocyclic ring has attracted wide spread attention due to their diverse applications as antibacterial-, antidepressant-, antiviral-, antitumorial- and antiinflammatory agents, pesticides, herbicides dyes, lubricant and analytical reagents.10,11 Among these, the commonly known systems are generally triazoles fused to pyridines, pyridazines, pyrimidines, pyrazines and triazines. The synthesis of 5-alkyl-4-amino-2-[(6-methyl[1,2,4]triazolo[3,4-b][1,3,4]thiadiazol-3yl)methyl]-2,4-dihydro-3H-1,2,4-triazol-3-ones (8a-d) were performed by the reaction of compounds 6a-d with acetic acid in the presence of phosphorus oxychloride.
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