A method for the preparation of methyl esters of β-1,2,4triazole-substituted alanines by condensation of methyl acrylate with 3,4-disubstituted-5-mercapto-1,2,4-triazoles has been developed. The optimal conditions for the process of hydrazinolysis of N-allyl derivatives of the obtained products were established. It is shown that to prevent the reduction of the allyl group, it is reasonable to carry out the process of hydrazinolysis in the presence of sodium sulfite. Based on hydrazides of β-1,2,4-triazole-substituted alanines, biheterocyclic compounds of a new structure -1,2,4-triazole-and 1,3,4oxadiazole-1,2,4-triazoles were synthesized.ChemistrySelect 2018, 3, 9981 -9985
Screening in a series of 1,2,4‐triazole derivatives has revealed an antinematode property in relation to positive nematodes. A certain relationship has been established between the structure and biological activity of the proposed compounds. It has been experimentally proved, that if the sulfur is present in molecules in the thionic form only, it leads to an increase in the viability of nematodes by 3–4%, and if compounds contain only the thiol form, it decreases the viability of nematodes by 20–40% depending on the concentration of the compounds used. It was also found that bis‐triazoles containing only the thiol form demonstrated antifungal activity, inhibiting the growth of C. albicans by 35–40%.
A study was carried out on the regioselectivity of the electrophilic halocyclization of 4‐allyl‐5‐substituted‐2,4‐dihydro‐3H‐1,2,4‐triazol‐3‐thiones by the action of bromine and iodine. It was revealed which factors influence the structure of the reaction products. 6‐(Bromomethyl)‐3‐substituted‐5,6‐dihydrothiazolo[2,3‐c]‐[1,2,4]triazoles have been shown to be good starting materials for the synthesis of polyheterocyclic systems containing a 1,2,3‐triazole ring. In contrast, 6‐iodo‐3‐substituted‐6,7‐dihydro‐5H‐[1,2,4]triazolo[3,4‐b][1,3]thiazines do not undergo azidation. Due to the dehydrohalogenation reaction, a double bond is formed.
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