ALKYLTHIOBENZOTHIAZOLES DECORATED WITH 1,2,3-TRIAZOLE
DOI:
https://doi.org/10.15421/jchemtech.v32i4.316457Keywords:
2-(but-1-yn-4-ylthio)benzothiazole, 2-(pent-1-yn-5-ylthio)benzothiazole, cycloaddition, click-reaction, 1,2,3-triazole, ; hybrid heterocycleAbstract
Triazole and its hybrid derivatives exhibit a range of biological activities, that is why the synthesis of hybrid heterocycles that contain triazole and benzothiazole rings is relevant. The aim of the current study is the investigation of the use of terminal butynyl and pentynyl thioethers of benzothiazole in the copper catalytic reaction of 1,3-dipolar cycloaddition of azides. 2-(but-1-yn-4-ylthio)- and 2-(pent-1-yn-5-ylthio)-benzothiazoles were synthesized for the first time in high yields via alkylation of 2-mercaptobenzothiazole with terminal butynyl and pentynyl bromides. Long-chain alkynyl thioethers of benzothiazole were used in copper catalytic reactions of 1,3-dipolar cycloaddition with aromatic and aliphatic azides. Based on experimental data, it was established that when using butynyl thioether in the reaction with phenylazide, the most effective solvent was a mixture of tetrahydrofuran and water. While the cycloaddition of pentynyl thioether with phenyl and benzyl azides was carried out in a dimethylformamide-water mixture. As a result, the new hybrid 1,2,3-triazolylthiobenzothiazoles, which can potentially exhibit high bioactivity, were synthesized in high yields and separated by two or three methylene spacers.
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