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Regio- and Stereoselective Synthesis of Functionalized Vinyl Sulfides Based on Pyridine-2-thiol and Propynoic Acid and Its Derivatives

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Abstract

Regio- and stereoselective methods of synthesis of 3-(pyridin-2-ylsulfanyl)prop-2-enoic acid and alkyl (Z)-3-(pyridin-2-ylsulfanyl)prop-2-enoates have been developed on the basis of nucleophilic addition of pyridine-2-thiol to propynoic acid and alkyl propynoates. Reactions of alkyl (Z)-3-(pyridin-2-ylsulfanyl)prop-2- enoates with methyl iodide afforded 2-[(3-alkoxy-3-oxoprop-1-enyl)sulfanyl]-1-methylpyridinium iodides.

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Authors and Affiliations

  1. Favorskii Irkutsk Institute of Chemistry, Siberian Branch, Russian Academy of Sciences, ul. Favorskogo 1, Irkutsk, 664033, Russia

    V. A. Potapov, R. S. Ishigeev, M. V. Musalov, S. V. Zinchenko, Yu. A. Chuvashev, T. N. Borodina & S. V. Amosova

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  1. V. A. Potapov
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  2. R. S. Ishigeev
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  3. M. V. Musalov
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  4. S. V. Zinchenko
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  5. Yu. A. Chuvashev
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  6. T. N. Borodina
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  7. S. V. Amosova
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Corresponding author

Correspondence to V. A. Potapov.

Additional information

Original Russian Text © V.A. Potapov, R.S. Ishigeev, M.V. Musalov, S.V. Zinchenko, Yu.A. Chuvashev, T.N. Borodina, S.V. Amosova, 2018, published in Zhurnal Organicheskoi Khimii, 2018, Vol. 54, No. 12, pp. 1784–1788.

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Potapov, V.A., Ishigeev, R.S., Musalov, M.V. et al. Regio- and Stereoselective Synthesis of Functionalized Vinyl Sulfides Based on Pyridine-2-thiol and Propynoic Acid and Its Derivatives. Russ J Org Chem 54, 1798–1802 (2018). https://doi.org/10.1134/S1070428018120102

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  • DOI: https://doi.org/10.1134/S1070428018120102

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