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Regioselective Reactions of Pyridine-2-sulfenyl Bromide with Vinyl and Allyl Ethers

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Abstract

Annulation reactions of pyridine-2-sulfenyl bromide with vinyl and allyl ethers proceeded regioselectively, but with opposite regiochemistry. Reactions with vinyl ethers led to 3-organyloxy-2,3-dihydro[1,3]thiazolo[3,2-a]pyridin-4-ium bromides (91–99% yields), while allyl ethers gave 2-substituted derivatives of 2,3-dihydro[1,3]thiazolo[3,2-a]pyridin-4-ium (90–98% yields). Tricyclic condensed compounds were synthesized by reactions of pyridine-2-sulfenyl bromide with cyclic ethers (2,3-dihydrofuran, 3,4-dihydro-2H-pyran and 2,5-dihydrofuran).

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ACKNOWLEDGMENTS

Spectral measurements were carried out using the equipment of the Baikal Analytical Center for Collective Use of the Siberian Branch of the Russian Academy of Sciences.

Funding

This work was financially supported by the Russian Science Foundation (project no. 22-13-00339).

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Authors and Affiliations

  1. A.E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch of the Russian Academy of Sciences, 664033, Irkutsk, Russia

    R. S. Ishigeev, S. V. Amosova & V. A. Potapov

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  1. R. S. Ishigeev
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  2. S. V. Amosova
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  3. V. A. Potapov
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Correspondence to V. A. Potapov.

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Ishigeev, R.S., Amosova, S.V. & Potapov, V.A. Regioselective Reactions of Pyridine-2-sulfenyl Bromide with Vinyl and Allyl Ethers. Russ J Gen Chem 92, 1720–1727 (2022). https://doi.org/10.1134/S1070363222090146

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