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Regioselective Reaction of Pyridine-2-Sulfenyl Chloride with Isoeugenol

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Abstract

Proceeding from 2,2′-disulfanediyldipyridine and isoeugenol a regioselective one-pot synthesis was developed affording 3-(4-hydroxy-3-methoxyphenyl)-2-methyl-2H,3H-[1,3]thiazolo[3,2-a]pyridin-4-ium chloride in a 70% yield.

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References

  1. Nicolaou, K.C., J. Org. Chem., 2009, vol. 74, p. 951. doi 10.1021/jo802351b

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  2. Newman, D.J., J. Med. Chem., 2008, vol. 51, p. 2589. doi 10.1021/jm0704090

    Article  CAS  PubMed  Google Scholar 

  3. Lukevits, É., Chem. Heterocycl. Compd., 1995, vol. 31, p. 639. doi 10.1007/BF01169065

    Article  Google Scholar 

  4. Kedarnath, G. and Jain, V.K., Coord. Chem. Rev., 2013, vol. 257, p. 1409. doi 10.1016/j.ccr.2013.01.003

    Article  CAS  Google Scholar 

  5. Zhang, Y., Liu, B., Wu, X., Li, R., Ning, X., Liu, Y., Liu, Z., Ge, Z., Li, R., and Yin, Y., Bioorg. Med. Chem., 2015, vol. 23, p. 4815. doi 10.1016/j.bmc.2015.05.041

    Article  CAS  PubMed  Google Scholar 

  6. Pan, B.C., Chen, Z.H., Piras, G., Dutschman, G.E., Rowe, E.C., Cheng, Y.C., and Chu, S.H., J. Heterocycl. Chem., 1994, vol. 31, p. 177. doi 10.1002/jhet.5570310130

    Article  CAS  Google Scholar 

  7. Fahs, S., Rowther, F.B., Dennison, S.R., Patil-Sen, Y., Warr, T., and Snape, T.J., Bioorg. Med. Chem. Lett., 2014, vol. 24, p. 3430. doi 10.1016/j.bmcl.2014.05.087

    Article  CAS  PubMed  Google Scholar 

  8. Adamec, J., Beckert, R., Weiβ, D., Klimešová, V., Waisser, K., Möllmann, U., Kaustová, J., and Buchta, V., Bioorg. Med. Chem., 2007, vol. 15, p. 2898. doi 10.1016/j.bmc.2007.02.021

    Article  CAS  PubMed  Google Scholar 

  9. Musalov, M.V., Potapov, V.A., Musalova, M.V., and Amosova, S.V., Russ. J. Org. Chem., 2014, vol. 50, p. 1702. doi 10.1134/S107042801411030X

    Article  CAS  Google Scholar 

  10. Musalov, M.V., Potapov, V.A., and Amosova, S.V., Russ. Chem. Bull., 2011, vol. 60, p. 767. doi 10.1007/s11172-011-0120-0

    Article  CAS  Google Scholar 

  11. Potapov, V.A., Malinovich, D.A., Amosova, S.V., Rusakov, Yu.Yu., and Bhasin, K.K., Chem. Heterocycl. Compd., 2012, vol. 48, p. 1129. doi 10.1007/s10593-012-1115-y

    Article  CAS  Google Scholar 

  12. Potapov, V.A., Ishigeev, R.S., and Amosova, S.V., Russ. J. Org. Chem., 2016, vol. 52, p. 918. doi 10.1134/S1070428016060300

    Article  CAS  Google Scholar 

  13. Potapov, V.A., Ishigeev, R.S., and Amosova, S.V., Russ. J. Org. Chem., 2017, vol. 53, p. 1604. doi 10.1134/S1070428017100219

    Article  CAS  Google Scholar 

  14. Borisov, A.V., Matsulevich, Zh.V., Osmanov, V.K., Borisova, G.N., Mammadova, G.Z., Maherramov, A.M., and Khrustalev, V.N., Chem. Heterocycl. Compd., 2012, vol. 48, p. 1098. doi 10.1007/s10593-012-1104-1

    Article  CAS  Google Scholar 

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Authors and Affiliations

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

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

Authors
  1. R. S. Ishigeev
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  2. V. A. Potapov
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  3. S. V. Amosova
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Corresponding author

Correspondence to S. V. Amosova.

Additional information

Original Russian Text © R.S. Ishigeev, V.A. Potapov, S.V. Amosova, 2018, published in Zhurnal Organicheskoi Khimii, 2018, Vol. 54, No. 8, pp. 1248–1249.

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Ishigeev, R.S., Potapov, V.A. & Amosova, S.V. Regioselective Reaction of Pyridine-2-Sulfenyl Chloride with Isoeugenol. Russ J Org Chem 54, 1262–1264 (2018). https://doi.org/10.1134/S1070428018080249

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  • DOI: https://doi.org/10.1134/S1070428018080249

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