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Regioselective Synthesis of 3-[2-(Alkylsulfanyl)ethyl]pyrazoles by Reaction of Alkanethiols with 3-Alkenylpyrazoles

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Abstract

3-Alkenyl-5-chloropyrazoles reacted with alkanethiols on heating to 60°C to afford in good yields 3-[2-(alkylsulfanyl)ethyl]-5-chloropyrazoles as a result of anti-Markovnikov addition to the alkenyl group.

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References

  1. Fustero, S., Sanchez-Rosello, M., Barrio, P., and Simon-Fuentes, A., Chem. Rev., 2011, vol. 111, p. 6984.

    Article  CAS  PubMed  Google Scholar 

  2. Janin, Y.L., Chem. Rev., 2012, vol. 112, p. 3924.

    Article  CAS  PubMed  Google Scholar 

  3. Elguero, J., Goya, P., Jagerovic, N., and Silva, A.M.S., Targets in Heterocyclic Systems. Chemistry and Properties, Attanasi, O.A. and Spinelli, D., Rome: Ital. Soc. Chem., 2003, vol. 6, p. 53.

    Google Scholar 

  4. Pérez-Fernández, R., Goya, P., and Elguero, J., Arkivoc, 2014, part (ii), p. 233.

    Google Scholar 

  5. Schmidt, A. and Dreger, A., Curr. Org. Chem., 2011, vol. 15, p. 1423.

    Article  CAS  Google Scholar 

  6. Schmidt, A. and Dreger, A., Curr. Org. Chem., 2011, vol. 15, p. 2897.

    Article  CAS  Google Scholar 

  7. Pizzuti, L., Barschak, A.G., Stefanello, F.M., Farias, M.D., Lencina, C., Roesch-Ely, M., Cunico, W., Moura, S., and Pereira, C.M.P., Curr. Org. Chem., 2014, vol. 18, p. 115.

    Article  CAS  Google Scholar 

  8. Ivachtchenko, A.V., Russ. Chem. Rev., 2014, vol. 83, p. 439.

    Article  CAS  Google Scholar 

  9. Gouda, M.A., Abu-Hashem, A.A., Saad, H.H., and Elattar, K.M., Res. Chem. Intermed., 2016, vol. 42, p. 2119.

    Article  CAS  Google Scholar 

  10. Joo-Yong, Y., Sang-gi, L., and Hyunik, S., Curr. Org. Chem., 2011, vol. 15, p. 657.

    Google Scholar 

  11. Bakr, F.A.W., Rizk, E.K., and Abdelbasset, A.F., Arkivoc, 2011, part (i), p. 196.

    Google Scholar 

  12. Khidre, R.E., Mohamed, H.A., and Abdel-Wahab, B.F., Turk. J. Chem., 2013, vol. 37, p. 1.

    Article  CAS  Google Scholar 

  13. Türkoglu, G., Ulldemolins, C.P., Müller, R., Hübner, E., Heinemann, F.W., Wolf, M., and Burzlaff, N., Eur. J. Inorg. Chem., 2010, p. 2962.

    Google Scholar 

  14. Han, L.C.M. and Timmons, R.B., Chem. Mater., 1998, vol. 10, p. 1422.

    Article  CAS  Google Scholar 

  15. Chang, S.Y., Chen, J.L., and Chi, Y., Inorg. Chem., 2007, vol. 46, p. 11 202.

    Article  CAS  Google Scholar 

  16. Fokin, S., Ovcharenko, V., Romanenko, G., and Ikorskii, V., Inorg. Chem., 2004, vol. 43, p. 969.

    Article  CAS  PubMed  Google Scholar 

  17. Cavero, E., Uriel, S., Romero, P., Serrano, J.L., and Gimenez, R., J. Am. Chem. Soc., 2007, vol. 129, p. 11 608.

    Article  CAS  Google Scholar 

  18. Tebbji, K., Bouabdellah, I., Aouniti, A., Hammouti, B., Oudda, H., Benkaddour, M., and Ramdani, A., Mater. Lett., 2007, vol. 61, p. 799.

    Article  CAS  Google Scholar 

  19. Junges, F., Kuhn, V.C.A., dos Santos, A.H.D.P., Rabello, C.R.K., Thomas, C.M., Carpentier, J.-F., and Casagrande, O.L., Organometallics, 2007, vol. 26, p. 4010.

    Article  CAS  Google Scholar 

  20. Guerrero, M., Pons, J., and Ros, J., J. Organomet. Chem., 2010, vol. 695, p. 1957.

    Article  CAS  Google Scholar 

  21. Lupidi, G., Marchetti, F., Masciocchi, N., Reger, D.L., Tabassum, S., Astolfi, P., Damiani, E., and Pettinari, C., J. Inorg. Biochem., 2010, vol. 104, p. 820.

    Article  CAS  PubMed  Google Scholar 

  22. Potapov, S., Nudnova, E.A., Domnina, G.A., Kirpotina, L.N., Quinn, M.T., Khlebnikov, A.I., and Schepetkin, I.A., Dalton Trans., 2009, p. 4488.

    Google Scholar 

  23. Bouwman, E., Driessen, W.L., and Reeddijk, J., Coord. Chem. Rev., 1990, vol. 104, p. 143.

    Article  CAS  Google Scholar 

  24. Es’kova, L.A., Erushnikova, L.A., Afonin, A.V., and Domnina, E.S., Russ. Chem. Bull., 1992, vol. 41, p. 1462.

    Article  Google Scholar 

  25. Maksimova, M.A., Cand. Sci. (Chem.) Dissertation, Irkutsk, 2007.

    Google Scholar 

  26. Levkovskaya, G.G., Kobelevskaya, V.A., Rudyakova, E.V., Ha, Q.K., Samultsev, D.O., and Rozentsveig, I.B., Tetrahedron, 2011, vol. 67, p. 1844.

    Article  CAS  Google Scholar 

  27. Levkovskaya, G.G., Rudyakova, E.V., Kobelevskaya, V.A., Popov, A.V., and Rozentsveig, I.B., Arkivoc, 2016, part (iii), p. 82

    Google Scholar 

  28. Rudyakova, E.V., Samultsev, D.O., Levanova, E.P., and Levkovskaya, G.G., Russ. J. Org. Chem., 2013, vol. 49, p. 734.

    Article  CAS  Google Scholar 

  29. Rudyakova, E.V., Samultsev, D.O., and Levkovskaya, G.G., Russ. J. Org. Chem., 2012, vol. 48, p. 1388.

    Article  CAS  Google Scholar 

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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. Kobelevskaya, A. V. Popov, G. G. Levkovskaya & I. B. Rozentsveig

  2. Irkutsk National Research Technical University, ul. Lermontova 83, Irkutsk, 664074, Russia

    E. V. Rudyakova

  3. Irkutsk State University, ul. Karla Marksa 1, Irkutsk, 664003, Russia

    I. B. Rozentsveig

Authors
  1. V. A. Kobelevskaya
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  2. A. V. Popov
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  3. G. G. Levkovskaya
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  4. E. V. Rudyakova
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  5. I. B. Rozentsveig
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Correspondence to V. A. Kobelevskaya.

Additional information

Original Russian Text © V.A. Kobelevskaya, A.V. Popov, G.G. Levkovskaya, E.V. Rudyakova, I.B. Rozentsveig, 2018, published in Zhurnal Organicheskoi Khimii, 2018, Vol. 54, No. 10, pp. 1493–1496.

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Kobelevskaya, V.A., Popov, A.V., Levkovskaya, G.G. et al. Regioselective Synthesis of 3-[2-(Alkylsulfanyl)ethyl]pyrazoles by Reaction of Alkanethiols with 3-Alkenylpyrazoles. Russ J Org Chem 54, 1505–1508 (2018). https://doi.org/10.1134/S1070428018100111

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  • DOI: https://doi.org/10.1134/S1070428018100111

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