Advertisement

Chemistry of Heterocyclic Compounds

, Volume 48, Issue 2, pp 258–279 | Cite as

Functionalization of pyrrolo[2,3-d]pyrimidine by palladium-catalyzed cross-coupling reactions (review)

  • S. TumkeviciusEmail author
  • J. Dodonova
Article

Palladium-catalyzed cross-coupling reactions (Heck, Sonogashira, Stille, Suzuki) in the pyrrolo-[2,3-d]pyrimidine series with emphasis on synthesis of biologically active and functional materials are reviewed.

Keywords

pyrrolo[2,3-d]pyrimidine biological activity cyclization fluorescence Heck reaction palladium catalysis Sonogashira reaction Stille reaction Suzuki reaction 

Notes

The Research Council of Lithuania is gratefully acknowledged for the support of the work (project No. MIP-65/2010).

References

  1. 1.
    R. J. Suhadolnik, Nucleoside Antibiotics, Wiley-Interscience, New York (1970), p. 315Google Scholar
  2. 2.
    R. J. Suhadolnik, Nucleosides as Biological Probes, Wiley, New York (1979), p. 158.Google Scholar
  3. 3.
    H. Nishioka, T. Sawa, H. Nakamura, H. Iinuma, D. Ikeda, R. Sawa, H. Naga M. Hamada, T. Takeuchi, I. Iitaka, and K. Umezawa, J. Nat. Prod., 54, 1321 (1991).CrossRefGoogle Scholar
  4. 4.
    E. C. Taylor, D. Kuhnt, C. Shih, S. M. Moran, J. Med. Chem., 35, 4450 (1992).CrossRefGoogle Scholar
  5. 5.
    J. Tsuji, Palladium Reagents and Catalysts. Innovations in Organic Synthesis, J. Wiley and Sons, Chichester (1999).Google Scholar
  6. 6.
    J. J. Li and G. W. Gribble, Palladium in Heterocyclic Chemistry, Pergamon, Amsterdam (2000).Google Scholar
  7. 7.
    Z. Chen, A. M. Venkatesan, C. M. Dehnhardt, A. Ayral-Kaloustian, N. Brooijmans, R. Mallon, L. Feldberg, I. Hollander, J. Lucas, K. Yu, F. Kong, and T. S. Mansour, J. Med. Chem., 53, 3169 (2010).CrossRefGoogle Scholar
  8. 8.
    S. Tumkevicius, J. Dodonova, K. Kazlauskas, V. Masevicius, L. Skardziute, and S. Jursenas, Tetrahedron Lett., 51, 3902 (2010).CrossRefGoogle Scholar
  9. 9.
    S. Tumkevicius and J. Dodonova, Synlett, 1705 (2011).Google Scholar
  10. 10.
    J. Dodonova, L. Skardziute, K. Kazlauskas, S. Jursenas, and S. Tumkevicius, Tetrahedron, 68, 329 (2012).CrossRefGoogle Scholar
  11. 11.
    R. J. Gillespie, I. A. Cliffe, C. E. Dawson, C. T. Dourish, S. Gaur, A. M. Jordan, A. R. Knight, J. Lerpiniere, A. Misra, R. M. Pratt, J. Roffey, G. C. Stratton, R. Upton, S. M. Weiss, and D. S. Williamson, Bioorg. Med. Chem. Lett., 18, 2924 (2008).CrossRefGoogle Scholar
  12. 12.
    A. D. Khoje, A. Kulendrn, C. Charnock, B. Wan, S. Franzblau, and L.-L. Gundersen, Bioorg. Med. Chem., 18, 7274 (2010).CrossRefGoogle Scholar
  13. 13.
    P. Nauš, R. Pohl, I. Votruba, P. Džubák, M. Hajdúch, R. Ameral, G. Birkuš, T. Wang, A. S. Ray, R. Mackman, T. Cihlář, and M. Hocek, J. Med. Chem., 53, 460 (2010).CrossRefGoogle Scholar
  14. 14.
    P. Perlikova, R. Pohl, I. Votruba, R. Shih, G. Birkus, T. Cihlar, and M. Hocek, Bioorg. Med. Chem., 19, 229 (2011).CrossRefGoogle Scholar
  15. 15.
    A. Gangjee, J. Yu, R. L. Kisliuk, W. H. Haile, G. Sobrero, and J. J. McGuire, J. Med. Chem., 46, 591 (2003).CrossRefGoogle Scholar
  16. 16.
    R. Selig, D. Schollmeyer, W. Albrecht, and S. Laufer, Tetrahedron, 67, 9204 (2011)CrossRefGoogle Scholar
  17. 17.
    J. Dodonova, I. Uogintaite, V. Masevicius, and S. Tumkevicius, Khim. Geterotsikl. Soedin. 1391 (2010). [Chem. Heterocycl. Compd., 46, 1122 (2010).]Google Scholar
  18. 18.
    Q. Lin, D. Meloni, Y. Pan, M. Xia, J. Rodgers, S. Shepard, M. Li, L. Galya, B. Metcalf, T.-Y. Yue, P. Liu and J. Zhou, Org. Lett., 11, 1999 (2009).CrossRefGoogle Scholar
  19. 19.
    T. Wang, M. W. Ledeboer, J. P. Duffy, A. C. Pierce, H. J. Zucolla, E. Block, D. Shlyakter, J. K. Hogan, and Y. L. Bennani, Bioorg. Med. Chem. Lett., 20, 153 (2010).CrossRefGoogle Scholar
  20. 20.
    A. J. Cocuzza, D. R. Chidester, S. Culp, L. Fitzgerald, and P. Gilligan, Bioorg. Med. Chem. Lett., 9 , 1063 (1999).CrossRefGoogle Scholar
  21. 21.
    A. Arcadi, S. Cacchi, M. Delmastro, and F. Marinella, Synlett, 409 (1991).Google Scholar
  22. 22.
    S. Tumkevicius and V. Masevicius, Synlett, 2327 (2004).Google Scholar
  23. 23.
    S. Tumkevicius and V. Masevicius, Synthesis, 3815 (2007).Google Scholar
  24. 24.
    F. W. Hobbs, Jr., J. Org. Chem., 54, 3420 (1989).CrossRefGoogle Scholar
  25. 25.
    M. J. Robins, R. S. Vinayak, and S. G. Wood, Tetrahedron Lett., 31, 3731 (1990).CrossRefGoogle Scholar
  26. 26.
    E. D. Edstrom, and Y. Wei, J. Org. Chem., 59, 6902 (1994).CrossRefGoogle Scholar
  27. 27.
    C. Shih and Y. Hu, Tetrahedron Lett., 35, 4677 (1994).CrossRefGoogle Scholar
  28. 28.
    H. Rosemeyer, N. Ramzaeva, E.-M. Becker, E. Feiling, and F. Seela, Bioconjugate Chem., 13, 1274 (2002).CrossRefGoogle Scholar
  29. 29.
    L. Zhang, Y. Zhang, X. Li, and L. Zhang, Bioorg. Med. Chem., 10, 907 (2002).CrossRefGoogle Scholar
  30. 30.
    C. M. McKeen, L. J. Brown, J. T. G. Nicol, J. M. Mellor, and T. Brown, Org. Biomol. Chem., 1, 2267 (2003).CrossRefGoogle Scholar
  31. 31.
    Y. Saito, Y. Miyauchi, A. Okamoto, and I. Saito, Chem. Commun., 1704 (2004).Google Scholar
  32. 32.
    S. Jäger, G. Rasched, H. Kornreich-Leshem, M. Engeser, O. Thum, and M. Famulok, J. Am. Chem. Soc., 127, 15071 (2005).CrossRefGoogle Scholar
  33. 33.
    F. Seela and K. I. Shaikh, Tetrahedron, 61, 2675 (2005).CrossRefGoogle Scholar
  34. 34.
    F. Seela, X. Peng, and X. Ming, Nucleosides, Nucleotides Nucleic Acids, 24, 839 (2005).CrossRefGoogle Scholar
  35. 35.
    F. Seela and X. Peng, J. Org. Chem, 71, 81 (2006).CrossRefGoogle Scholar
  36. 36.
    F. Seela and X. Ming, Tetrahedron, 63, 9850 (2007).CrossRefGoogle Scholar
  37. 37.
    X. Peng and F. Seela, Nucleosides, Nucleotides Nucleic Acids, 26, 603 (2007).CrossRefGoogle Scholar
  38. 38.
    Q. Meng, D. H. Kim, X. Bai, L. Bi, N. J. Turro, and J. Ju, J. Org. Chem., 71, 3248 (2006).CrossRefGoogle Scholar
  39. 39.
    P. M. E. Gramlich, C. T. Wirges, J. Gierlich, and T. Carell, Org. Lett., 10, 249 (2008).CrossRefGoogle Scholar
  40. 40.
    R. Varghese, P. K. Gajula, T. K. Chakraborty, and H.-A. Wagenknecht, Synlett, 20, 3252 (2009).Google Scholar
  41. 41.
    J. Riedl, P. Horáková, P. Šebest, R. Pohl, L. Havran, M. Fojta, and M. Hocek, Eur. J. Org. Chem., 3519 (2009).Google Scholar
  42. 42.
    M. Vrábel, R. Pohl, I. Votruba, M. Sajadi, S. A. Kovalenko, N. P. Ernsting, and M. Hocek, Org. Biomol. Chem., 6, 2852 (2008).CrossRefGoogle Scholar
  43. 43.
    S. Ikonen, H. Macíčková-Cahová, R. Pohl, M. Šanda, and M. Hocek, Org. Biomol. Chem., 8, 1194 (2010).CrossRefGoogle Scholar
  44. 44.
    F. Seela and M. Zulauf, Synthesis, 726 (1996).Google Scholar
  45. 45.
    P. Čapek, H. Cahová, R. Pohl, M. Hocek, C. Gloeckner, and A. Marx, Chem.–Eur. J., 13, 6196 (2007).CrossRefGoogle Scholar
  46. 46.
    P. Kielkowski, R. Pohl, and M. Hocek, J. Org. Chem., 76, 3457 (2011).CrossRefGoogle Scholar
  47. 47.
    A. Gangjee, J. Yu, J. J. McGuire, V. Cody, N. Galitsky, R. L. Kisliuk, and S. F. Queener, J. Med. Chem., 43, 3837 (2000).CrossRefGoogle Scholar
  48. 48.
    A. Gangjee, J. Yu, J. E. Copper, and C. D. Smith, J. Med. Chem., 50, 3290 (2007).CrossRefGoogle Scholar
  49. 49.
    E. D. Edstrom and Y. Wei, J. Org. Chem., 58, 403 (1993).CrossRefGoogle Scholar
  50. 50.
    T. Sakamoto, Y. Kondo, S. Sato, and H. Yamanaka, Tetrahedron Lett., 35, 2919 (1994).CrossRefGoogle Scholar
  51. 51.
    C. J. Calderwood, D. N. Johnston, R. Munschauer, and P. Rafferty, Bioorg. Med. Chem. Lett., 12, 1683 (2002).CrossRefGoogle Scholar
  52. 52.
    B. G. Ugarkar, A. J. Castellino, J. M. DaRe, J. J. Kopcho, J. B. Wiesner, J. M. Schanzer, and M. D. Erion, J. Med. Chem., 43, 2894 (2000).CrossRefGoogle Scholar
  53. 53.
    S. H. Boyer, B. G. Ugarkar, J. Solbach, J. Kopcho, M. C. Matelich, K. Ollis, J. E. Gomez-Galeno, R. Mendonca, M. Tsuchiya, A. Nagahisa, M. Nakane, J. B. Wiesner, and M. D. Erion, J. Med. Chem., 48, 6430 (2005).CrossRefGoogle Scholar
  54. 54.
    T. Y. H. Wu, P. G. Schultz, and S. Ding, Org. Lett., 5, 3587 (2003).CrossRefGoogle Scholar
  55. 55.
    H. Cahová, L. Havran, P. Brázdilová, H. Pivonková, R. Pohl, M. Fojta, and M. Hocek, Angew. Chem., Int. Ed., 47, 2059 (2008).CrossRefGoogle Scholar
  56. 56.
    H. Macíčková-Cahová, R. Pohl, P. Horáková, L. Havran, J. Špaček, M. Fojta, and M. Hocek, Chem.–Eur. J., 17, 5833 (2011).CrossRefGoogle Scholar
  57. 57.
    V. Raindlová, R. Pohl, M. Šanda, and M. Hocek, Angew. Chem., Int. Ed., 49, 1064 (2010).CrossRefGoogle Scholar
  58. 58.
    J. H. Harvey, B. K. Butler, and D. Trauner, Tetrahedron Lett., 48, 1661 (2007).CrossRefGoogle Scholar
  59. 59.
    M. Singer and A. Jäschke, J. Am. Chem. Soc., 132, 8372 (2010).CrossRefGoogle Scholar
  60. 60.
    W. Zhou. D. Ercan, P. A. Jänne, and N. S. Gray, Bioorg. Med. Chem. Lett., 21, 638 (2011).CrossRefGoogle Scholar
  61. 61.
    A. Okamoto, T. Taiji, K. Tanaka, and I. Saito, Tetrahedron Lett., 41, 10035 (2000).CrossRefGoogle Scholar
  62. 62.
    T. Angelov, A. Guainazzi, and O. B. Schärer, Org. Lett., 11, 661 (2009).CrossRefGoogle Scholar
  63. 63.
    C. A. Buhr, M. D. Mateucci, and B. C. Froehler, Tetrahedron Lett., 40, 8969 (1999).CrossRefGoogle Scholar
  64. 64.
    I. Saito, Y. Miyauchi, Y. Saito, and K. Fujimoto, Tetrahedron Lett., 46, 97 (2005).CrossRefGoogle Scholar
  65. 65.
    Y. Hirama, H. Abe, N. Minakawa, and A. Matsuda, Tetrahedron, 66, 8402 (2010).CrossRefGoogle Scholar
  66. 66.
    B. Dyck and J. R. McCarthy, Heterocycles, 62, 191 (2004).CrossRefGoogle Scholar
  67. 67.
    E. C. Taylor, W. B. Young, R. Chaudhari, and H. H. Patel, Heterocycles, 36, 1897 (1993).CrossRefGoogle Scholar
  68. 68.
    E. C. Taylor, W. B. Young, and C. Spanka, J. Org. Chem., 61, 1261(1996).CrossRefGoogle Scholar
  69. 69.
    A. Gangjee, J. Yu, and R. L. Kisliuk, J. Heterocyclic. Chem., 39, 833 (2002).CrossRefGoogle Scholar
  70. 70.
    C. J. Pink, H. Wong, F. C. Ferreira, and A. G. Livingston, Org. Process Res. Dev., 12, 589 (2008).CrossRefGoogle Scholar
  71. 71.
    C. Torborg and M. Beller, Adv. Synth. Catal., 351, 3027 (2009).CrossRefGoogle Scholar
  72. 72.
    V. W. Rosso, D. A. Lust, P. J. Bernot, J. A. Grosso, S. P. Modi, A. Rusowicz, T. C. Sedergran, J. H. Simpson, S. K. Srivastava, M. J. Humora, and N. G. Anderson, Org. Process Res. Dev., 1, 311 (1997).CrossRefGoogle Scholar
  73. 73.
    G. Kerric, E. Le Grognec, F. Zammattio, M. Paris, and J.-P. Quintard, J. Organomet. Chem., 695, 103 (2010).CrossRefGoogle Scholar

Copyright information

© Springer Science+Business Media, Inc. 2012

Authors and Affiliations

  1. 1.Vilnius UniversityVilniusLithuania

Personalised recommendations