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Synthesis and Halogenation of 2-(1,2,3-Thiadiazol-4-yl)-5-methylthiophene

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Abstract

By means of the Hurd–Mori reaction, 2-(1,2,3-thiadiazol-4-yl)-5-methyl-thiophene was synthesized. Its bromination with N-bromosuccinimide under conditions of radical initiation leads to a labile 2-bromomethyl derivative which, in the presence of proton donors or when heated, rearranges to 2-(1,2,3-thiadiazol-4-yl)-4-bromo-5-methylthiophene. The possibility of rearrangement was confirmed by quantum chemical calculations. Chlorination of 2-(1,2,3-thiadiazol-4-yl)-5-methylthiophene with sulfuryl chloride both in the presence of AIBN and without it leads to 2-(1,2,3-thiadiazol-4-yl)-3,4-dichloro-5-methylthiophene. Intermediate products that form in the course of both processes are established and schemes of their formation are offered. Bromination of 2-(1,2,3-thiadiazol-4-yl)-4-bromo- and -3,4-dichloro-5-methylthiophenes with N-bromosuccinimide proceeds at the methyl group. Obtained bromomethyl derivatives undergo nucleophilic substitution reactions in the usual manner.

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ACKNOWLEDGMENTS

The studies were carried out using the equipment of the St. Petersburg State University resource center “Methods for analyzing the composition of matter.”

Funding

The work was carried out within the framework of the state assignment of the Ministry of Science and Higher Education of Russia No. FSEN-2023-0002 using the equipment of the engineering center of the St. Petersburg State Technological Institute (Technical University).

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Authors and Affiliations

  1. St. Petersburg State Institute of Technology (Technical University), 190013, St. Petersburg, Russia

    L. M. Pevzner, M. L. Petrov, M. N. Krivchun, A. V. Belyakov & А. V. Stepakov

  2. St. Petersburg University, 199034, St. Petersburg, Russia

    А. V. Stepakov

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  1. L. M. Pevzner
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  2. M. L. Petrov
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  3. M. N. Krivchun
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  4. A. V. Belyakov
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  5. А. V. Stepakov
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Correspondence to L. M. Pevzner.

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Pevzner, L.M., Petrov, M.L., Krivchun, M.N. et al. Synthesis and Halogenation of 2-(1,2,3-Thiadiazol-4-yl)-5-methylthiophene. Russ J Gen Chem 93, 2926–2934 (2023). https://doi.org/10.1134/S1070363223110245

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  • DOI: https://doi.org/10.1134/S1070363223110245

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