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.
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This work was financially supported by the Russian Science Foundation (project no. 22-13-00339).
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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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DOI: https://doi.org/10.1134/S1070363222090146