Reductive alkylation of disulfides. Synthesis of 2-(alkylsulfanyl)-1H-pyrrole-3-carbonitriles

Abstract

Reaction of 2,2′-(disulfanediyl)bis(1H-pyrrole-3-carbonitriles) with alkyl halides in ethanol in the presence of sodium tetrahydridoborate afforded 2-(alkylsulfanyl)-1H-pyrrole-3-carbonitriles.

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References

  1. 1.

    Gongora-Benitez, M., Tulla-Puche, J., and Albericio, F., Chem. Rev., 2014, vol. 114, p. 901.

    CAS  Article  Google Scholar 

  2. 2.

    Fass, D., Annu. Rev. Biophys., 2012, vol. 41, p. 63.

    CAS  Article  Google Scholar 

  3. 3.

    Bulleid, N.J., Cold Spring Harbor Perspect. Biol., 2012, vol. 4, no. 11, a013219.

    Article  Google Scholar 

  4. 4.

    Bulleid, N.J. and Ellgaard, L., Trends Biochem. Sci., 2011, vol. 36, p. 485.

    CAS  Article  Google Scholar 

  5. 5.

    Zhao, E., Liu, H.L., Tsai, C.H., Tsai, H.K., Chan, C., and Kao, C.Y., Bioinformatics, 2005, vol. 21, p. 1415.

    CAS  Article  Google Scholar 

  6. 6.

    Chuang, C.C., Chen, C.Y., Yang, J.M., Lyu, P.C., and Hwang, J.K., Proteins, 2003, vol. 53, p. 1.

    CAS  Article  Google Scholar 

  7. 7.

    Hogg, P.J., Trends Biochem. Sci., 2003, vol. 28, p. 210.

    CAS  Article  Google Scholar 

  8. 8.

    Hogg, P.J., Redox Rep., 2002, vol. 7, p. 71.

    CAS  Article  Google Scholar 

  9. 9.

    Sevier, C.S. and Kaiser, C.A., Nat. Rev. Mol. Cell Biol., 2002, vol. 3, p. 836.

    CAS  Article  Google Scholar 

  10. 10.

    Wedemeyer, W.J., Welker, E., Narayan, M., and Scheraga, H.A., Biochemistry, 2000, vol. 39, p. 7032.

    CAS  Article  Google Scholar 

  11. 11.

    Ziegler, D.M., Annu. Rev. Biochem., 1985, vol. 54, p. 305.

    CAS  Article  Google Scholar 

  12. 12.

    Gilbert, H.F., Methods Enzymol., 1984, vol. 107, p. 330.

    CAS  Article  Google Scholar 

  13. 13.

    Meister, A. and Anderson, M.E., Annu. Rev. Biochem., 1983, vol. 52, p. 711.

    CAS  Article  Google Scholar 

  14. 14.

    Buchanan, B.B., Annu. Rev. Plant Physiol., 1980, vol. 57, p. 209.

    Google Scholar 

  15. 15.

    Kosower, N.S. and Kosower, E.M., Int. Rev. Cytol., 1978, vol. 54, p. 109.

    CAS  Article  Google Scholar 

  16. 16.

    Ghezzi, P., Free Radical Res., 2005, vol. 39, p. 573.

    CAS  Article  Google Scholar 

  17. 17.

    Fernandes, A.P. and Holmgren, A., Antioxid. Redox Signaling, 2004, vol. 6, p. 63.

    CAS  Article  Google Scholar 

  18. 18.

    Arner, E.S.J. and Holmgren, A., Eur. J. Biochem., 2000, vol. 267, p. 6102.

    CAS  Article  Google Scholar 

  19. 19.

    Holmgren, A., Structure, 1995, vol. 3, p. 239.

    CAS  Article  Google Scholar 

  20. 20.

    Gongora-Benitez, M., Tulla-Puche, J., and Albericio, F., Chem. Rev., 2014, vol. 114, p. 901.

    CAS  Article  Google Scholar 

  21. 21.

    Kishore, V.J., Hu, W.-P., Chen, C.-Y., and Wang, J.-J., Tetrahedron, 2011, vol. 67, p. 8895.

    Article  Google Scholar 

  22. 22.

    Ruano, J.L.G., Parra, A., and Aleman, J., Green Chem., 2008, vol. 10, p. 706.

    Article  Google Scholar 

  23. 23.

    Mealli, C., Ienco, A., Poduska, A., and Hoffmann, R., Angew. Chem., Int. Ed., 2008, vol. 47, p. 2864.

    CAS  Article  Google Scholar 

  24. 24.

    Witt, D., Synthesis, 2008, p. 2491.

    Google Scholar 

  25. 25.

    Duncia, J.V., Santella, J.B. III, Higley, C.A., Pitts, W.J., Wityak, J., Frietze, W.E., Rankin, F.W., Sun, J.-H., Earl, R.A., Tabaka, A.C., Teleha, C.A., Blom, K.F., Favata, M.F., Manos, E.J., Daulerio, A.G., Stradley, D.A., Horiuchi, K., Copeland, R.A., Scherle, P.A., Trzaskos, J.M., Magolda, R.L., Trainor, G.L., Wexler, R.R., Hobbs, F.W., and Olson, R.E., Bioorg. Med. Chem. Lett., 1998, vol. 8, p. 2839.

    CAS  Article  Google Scholar 

  26. 26.

    Gonzalez, I.C., Davis, L.N., and Smith, C.K. I., Bioorg. Med. Chem. Lett., 2004, vol. 14, p. 4037.

    CAS  Article  Google Scholar 

  27. 27.

    Fernandez, M.-C., Castano, A., Dominguez, E., Escribano, A., Jiang, D., Jimenez, A., Hong, E., Hornback, W.J., Nisenbaum, E.S., Rankl, N., Tromiczak, E., Vaught, G., Zarrinmayeh, H., and Zimmerman, D.M., Bioorg. Med. Chem. Lett., 2006, vol. 16, p. 5057.

    CAS  Article  Google Scholar 

  28. 28.

    Rewcastle, G.W., Palmer, B.D., Dobrusin, E.M., Fry, D.W., Kraker, A.J., and Denny, W.A., J. Med. Chem., 1994, vol. 37, p. 2033.

    CAS  Article  Google Scholar 

  29. 29.

    Thompson, A.M., Fry, D.W., Kraker, A.J., and Denny, W.A., J. Med. Chem., 1994, vol. 37, p. 598.

    CAS  Article  Google Scholar 

  30. 30.

    Thompson, A.M., Rewcastle, G.V., Tercel, M., Dobrusin, E.M., Fry, D.W., Kraker, A.J., and Denny, W.A., J. Med. Chem., 1993, vol. 36, p. 2459.

    CAS  Article  Google Scholar 

  31. 31.

    Ranganathan, S. and Jayaraman, N., J. Chem. Soc., Chem. Commun., 1991, vol. 14, p. 934.

    Article  Google Scholar 

  32. 32.

    Barbier, M. and Devys, M., J. Heterocycl. Chem., 1989, vol. 26, p. 265.

    CAS  Article  Google Scholar 

  33. 33.

    Belikov, M.Yu., Fedoseev, S.V., Ievlev, M.Yu., Ershov, O.V., and Tafeenko, V.A., RSC Adv., 2015, vol. 5, p. 65316.

    CAS  Article  Google Scholar 

  34. 34.

    Sheldrick, G.M., Acta Crystallogr., Sect. A, 2008, vol. 64, p. 112.

    CAS  Article  Google Scholar 

  35. 35.

    Brandenburg, K., DIAMOND, Release 2.1d. Bonn, Germany: Crystal Impact, 2000.

    Google Scholar 

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Correspondence to S. V. Fedoseev.

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Original Russian Text © S.V. Fedoseev, M.Yu. Belikov, O.V. Ershov, V.A. Tafeenko, 2016, published in Zhurnal Organicheskoi Khimii, 2016, Vol. 52, No. 12, pp. 1793–1796.

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Fedoseev, S.V., Belikov, M.Y., Ershov, O.V. et al. Reductive alkylation of disulfides. Synthesis of 2-(alkylsulfanyl)-1H-pyrrole-3-carbonitriles. Russ J Org Chem 52, 1784–1787 (2016). https://doi.org/10.1134/S1070428016120125

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