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New strategies for the synthesis of N-alkylated indoles (Review)

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Chemistry of Heterocyclic Compounds Aims and scope

New data, mostly published in the last five years, on methods for the synthesis of N-alkylated indoles both as a result of direct introduction of the alkyl substituent at the nitrogen atom and by construction of the indole heterocyclic system are reviewed. Only examples of indole derivatives containing branched, sterically hindered, and chiral alkyl substituents at the nitrogen atom are discussed.

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References

  1. F.-E. Chen and J. Huang, Chem. Rev., 105, 4671 (2005).

    Article  CAS  Google Scholar 

  2. M. Ishikura and K. Yamada, Nat. Prod. Rep., 26, 803 (2009) and previous reviews of the series.

    Article  CAS  Google Scholar 

  3. W. Gul and M. T. Hamann, Life Science, 78, 442 (2005).

    Article  CAS  Google Scholar 

  4. M. Baumann, I. R. Baxendale, S. V. Ley, and N. Nikbin, Beilstein J. Org. Chem., 7, 442 (2011).

    Article  CAS  Google Scholar 

  5. B. E. Evans, K. E. Rittle, M. G. Bock, R. M. DiPardo, R. M. Freidinger, W. L. Whitter, G. F. Lundell, D. F. Verber, P. S. Anderson, R. S. L. Chang, V. J. Lotti, D. J. Cerino, T. B. Chen, P. J. Kling, K. A. Kunkel, J. P. Springer, and J. Hirshfield, J. Med. Chem., 31, 2235 (1988).

    Article  CAS  Google Scholar 

  6. D. A. Horton, G. T. Bourne, and M. L. Smythe, Chem. Rev., 103, 893 (2003).

    Article  CAS  Google Scholar 

  7. G. M. Cragg, P. G. Grothaus, and D. J. Newman, Chem. Rev., 109, 3012 (2009).

    Article  CAS  Google Scholar 

  8. A. J. Kochanowska-Karamyan and M. T. Hamann, Chem. Rev., 110, 4489 (2010).

    Article  CAS  Google Scholar 

  9. V. Sharma, P. Kumar, and D. Pathak, J. Heterocycl. Chem., 47, 491 (2010).

    CAS  Google Scholar 

  10. G. W. Gribble, J. Chem. Soc., Perkin Trans. 1, 1045 (2000).

  11. G. R. Humphrey and J. T. Kuethe, Chem. Rev., 106, 2875 (2006).

    Article  CAS  Google Scholar 

  12. R. Vicente, Org. Biomol. Chem., 9, 6469 (2011).

    Article  CAS  Google Scholar 

  13. D. F. Taber and P. K. Tirunahari, Tetrahedron, 67, 7195 (2011).

    Article  CAS  Google Scholar 

  14. M. Bandini and A. Eichholzer, Angew. Chem., Int. Ed., 48, 9608 (2009).

    Article  CAS  Google Scholar 

  15. I. Nakamura and Y. Yamamoto, Chem. Rev., 104, 2127 (2004).

    Article  CAS  Google Scholar 

  16. N. T. Patil and Y. Yamamoto, Chem. Rev., 108, 3395 (2008).

    Article  CAS  Google Scholar 

  17. S. Cacchi and G. Fabrizi, Chem. Rev., 111, PR215 (2011).

    Article  CAS  Google Scholar 

  18. J. E. R. Sadig and M. C. Willis, Synthesis, 1 (2011).

  19. S. Cacchi, G. Fabrizi, and A. Goggiomani, Org. Biomol. Chem., 9, 641 (2011).

    Article  CAS  Google Scholar 

  20. J. Barluenga, F. Rodriguez, and F. J. Fananas, Chem.-Asian J., 4, 1036 (2009).

    Article  CAS  Google Scholar 

  21. T. Vlaar, E. Ruijter, and R. V. A. Orru, Adv. Synth. Catal., 353, 809 (2011).

    Article  CAS  Google Scholar 

  22. J. J. Song, J. T. Reeves, D. R. Fandrick, Z. Tan, N. K. Yee, and C. H. Senanayake, ARKIVOC, i, 390 (2010).

  23. P. Thansandote and M. Lautens, Chem.-Eur. J., 15, 5874 (2009).

    Article  CAS  Google Scholar 

  24. I. V. Seregin and V. Gevorgyan, Chem. Soc. Rev., 36, 1173 (2007).

    Article  CAS  Google Scholar 

  25. B. J. Stokes and T. G. Driver, Eur. J. Org. Chem., 4071 (2011).

  26. J. Campo, M. Garcia-Valverde, S. Marcaccini, M. J. Rojo, and T. Torroba, Org. Biomol. Chem., 4, 757 (2006).

    Article  CAS  Google Scholar 

  27. G. Bartoli, G. Bencivenni, and R. Dalpozzo, Chem. Soc. Rev., 39, 4449 (2010).

    Article  CAS  Google Scholar 

  28. L. Joucla and L. Djakovitch, Adv. Synth. Catal., 351, 673 (2009).

    Article  CAS  Google Scholar 

  29. L. M. Levy, G. M. Cabrera, J. E. Wright, and A. M. Seldes, Phytochemistry, 54, 941 (2000).

    Article  CAS  Google Scholar 

  30. S.-M. Li, Nat. Prod. Rep., 27, 57 (2010).

    Article  Google Scholar 

  31. P. E. Mahaney, A. T. Vu, C. C. McComas, P. Zhang, L. M. Nogle, W. L. Watts, A. Sarkahian, L. Leventhal, N. R. Sullivan, A. J. Uveges, and E. J. Trybulski, Bioorg. Med. Chem., 14, 8455 (2006).

    Article  CAS  Google Scholar 

  32. T. I. Richardson, C. A. Clarke, K.-L. Yu, Y. K. Yee, T. J. Bleisch, J. E. Lopez, S. A. Jones, N. E. Hughes, B. S. Muehl, C. W. Lugar, T. L. Moore, P. K. Shetler, R. W. Zink, J. J. Osborne, C. Montrose-Rafizadeh, N. Patel, A. G. Geiser, R. J. Sells Galvin, and J. A. Dodge, ACS Med. Chem. Lett., 2, 148 (2011).

    Article  CAS  Google Scholar 

  33. A. Gonelli, C. Mischiati, R. Guerrini, R. Voltan, S. Salvadori, and G. Zauli, Mini-Rev. Med. Chem., 9, 498 (2009).

    Article  CAS  Google Scholar 

  34. R. Slade, Y. Klimova, R. J. Halter, A. J. Yungai, W. S. Weiner, R. J. Walton, J. A. Willardsen, M. B. Anderson, and K. Zavitz, US Pat. Appl. 2008249135.

  35. A. V. Karchava, I. S. Shuleva, A. A. Ovcharenko, and M. A. Yurovskaya, Khim. Geterotsikl. Soedin., 373 (2010). [Chem. Heterocycl. Compd., 46, 291 (2010).]

    Google Scholar 

  36. H. Xu, Mini-Rev. Org. Chem., 6, 367 (2009).

    Article  CAS  Google Scholar 

  37. H. Sugiyama, F. Yokokawa, T. Aoyama, and T. Shioiri, Tetrahedron Lett., 42, 7277 (2001).

    Article  CAS  Google Scholar 

  38. P. S. Baran, C. A. Guerrero, and E. J. Corey, J. Am. Chem. Soc., 125, 5628 (2003).

    Article  CAS  Google Scholar 

  39. H. Sugiyama, T. Shioiri, and F. Yokokawa, Tetrahedron Lett., 43, 3489 (2002).

    Article  CAS  Google Scholar 

  40. K. C. Kumara Swamy, N. N. Bhuvan Kumar, E. Balaraman, and K. V. P. Pavan Kumar, Chem. Rev., 109, 2551 (2009).

    Article  Google Scholar 

  41. G. Yagil, Tetrahedron, 23, 2855 (1967).

    Article  CAS  Google Scholar 

  42. A. Bombrun and G. Casi, Tetrahedron Lett., 43, 2187 (2002).

    Article  CAS  Google Scholar 

  43. N. E. Golantsov, A. V. Karchava, V. M. Nosova, and M. A. Yurovskaya, Izv. Akad. Nauk, Ser. Khim., 221 (2005). [Russ. Chem. Bull., 54, 226 (2005).]

    Google Scholar 

  44. J. K. Laha and G. D. Cuny, J. Org. Chem., 76, 8477 (2011).

    Article  CAS  Google Scholar 

  45. S. S. Bhagwat and C. Gude, Tetrahedron Lett., 35, 1847 (1994).

    Article  CAS  Google Scholar 

  46. W. Frohner, B. Monse, T. M. Braxmeier, L. Casiraghi, H. Sahagun, and P. Seneci, Org. Lett., 7, 4573 (2005).

    Article  Google Scholar 

  47. S. Messaoudi, F. Anizon, B. Pfeiffer, and M. Prudhomme, Tetrahedron, 61, 7304 (2005).

    Article  CAS  Google Scholar 

  48. H.-L. Cui, X. Feng, J. Peng, J. Lei, K. Jiang, and Y.-C. Chen, Angew. Chem., Int. Ed., 48, 5737 (2009).

    Article  CAS  Google Scholar 

  49. Y. Xie, Y. Zhao, B. Qian, L. Yang, C. Xia, and H. Huang, Angew. Chem., Int. Ed., 50, 5682 (2011).

    Article  CAS  Google Scholar 

  50. D. Enders, C. Wang, and G. Raabe, Synthesis, 4119 (2009).

  51. L. Hong, W. Sun, C. Liu, L. Wang, and R. Wang, Chem.-Eur. J., 16, 440 (2010).

    Article  CAS  Google Scholar 

  52. M. Bandini, A. Eichholzer, M. Tragni, and A. Umani-Ronchi, Angew. Chem., Int. Ed., 47, 3238 (2008).

    Article  CAS  Google Scholar 

  53. M. Bandini, A. Bottoni, A. Eichholzer, G. P. Miscione, and M. Stenta, Chem.-Eur. J., 16, 12462 (2010).

    Article  CAS  Google Scholar 

  54. Q. Cai, C. Zheng and S.-L. You, Angew. Chem., Int. Ed., 49, 8666 (2010).

    Article  CAS  Google Scholar 

  55. B. M. Trost, M. J. Krische, V. Berl, and E. M. Grenzer, Org. Lett., 4, 2005 (2002).

    Article  CAS  Google Scholar 

  56. M. Bandini, A. Melloni, and A. Umani-Ronchi, Org. Lett., 6, 3199 (2004).

    Article  CAS  Google Scholar 

  57. L. M. Stanley and J. F. Hartwig, Angew. Chem., Int. Ed., 48, 7841 (2009).

    Article  CAS  Google Scholar 

  58. M. R. Luzung, C. A. Lewis, and P. S. Baran, Angew. Chem., Int. Ed., 48, 7025 (2009).

    Article  CAS  Google Scholar 

  59. H. Schirok, Synthesis, 1404 (2008).

  60. A. J. Fletcher, M. N. Bax, and M. C. Willis, Chem. Commun., 4764 (2007).

  61. M. C. Willis, G. N. Brace, and I. P. Holmes, Angew. Chem., Int. Ed., 44, 403 (2005).

    Article  CAS  Google Scholar 

  62. M. C. Willis, G. N. Brace, T. J. K. Findlay, and I. P. Holmes, Adv. Synth. Catal, 348, 851 (2006).

    Article  CAS  Google Scholar 

  63. F. S. Melkonyan, A. V. Karchava, and M. A. Yurovskaya, J. Org. Chem., 73, 4275 (2008).

    Article  CAS  Google Scholar 

  64. F. S. Melkonyan, A. P. Topol'yan, A. V. Karchava, and M. A. Yurovskaya, Khim. Geterotsikl. Soedin., 1581 (2008). [Chem. Heterocycl. Compd., 44, 1288 (2008).]

    Google Scholar 

  65. L. Ackermann, R. Sandmann, and M. V. Kondrashov, Synlett, 1219 (2009).

  66. L. Ackermann, R. Sandmann, M. Schinkel, and M. V. Kondrashov, Tetrahedron, 65, 8930 (2009).

    Article  CAS  Google Scholar 

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Authors and Affiliations

  1. M. V. Lomonosov Moscow State University, 1, Bld. 3, Leninskie Gory, Moscow, 119991, Russia

    A. V. Karchava, F. S. Melkonyan & M. A. Yurovskaya

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  1. A. V. Karchava
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  2. F. S. Melkonyan
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  3. M. A. Yurovskaya
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Correspondence to A. V. Karchava.

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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 3, pp. 415-433, March, 2012.

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Karchava, A.V., Melkonyan, F.S. & Yurovskaya, M.A. New strategies for the synthesis of N-alkylated indoles (Review). Chem Heterocycl Comp 48, 391–407 (2012). https://doi.org/10.1007/s10593-012-1006-2

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