Direct synthesis of benzo[a]carbazoles by palladium-catalyzed domino reactions: synthesis and photophysical properties of diverse benzo[a]carbazoles

Abstract

A direct, concise, and atom-economical synthetic method for the generation of benzo[a]carbazoles, using a palladium-catalyzed reaction has been developed. The reaction produces gave various benzo[a]carbazoles in good to excellent yields, through Knoevenagel condensation followed by intramolecular ortho-arylation. The synthetically attractive feature of the procedure is reflected by its applicability to a wide range of indole and bromobenzaldehyde derivatives. Mechanistic aspects of the reaction involves the formation of a single isomer of two possible products which leads to the formation of benzo[a]carbazoles via a palladium-catalyzed C–H bond functionalization reaction. The development of the annulation reaction with a wide substrate scope provided a unique opportunity to evaluate photophysical properties of a series of benzo[a]carbazoles. Almost all the compounds evaluated in this study were found to emit purple to blue light in the visible region. Some interesting structure–property correlations are also described.

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References

  1. 1.

    A.W. Schmidt, K.R. Reddy, H.-J. Knölker, Chem. Rev. 112, 3193 (2012)

    Article  CAS  Google Scholar 

  2. 2.

    H. Nakano, S. Ōmura, J. Antibiot. 62, 17 (2009)

    Article  CAS  Google Scholar 

  3. 3.

    M. Prudhomme, Eur. J. Med. Chem. 38, 123 (2003)

    Article  CAS  Google Scholar 

  4. 4.

    C.M. Cavazos, S.T. Keir, T. Yoshinari, D.D. Bigner, H.S. Friedman, Cancer Chemother. Pharmacol. 48, 250 (2001)

    Article  CAS  Google Scholar 

  5. 5.

    E. Conchon, F. Anizon, B. Aboab, M. Prudhomme, J. Med. Chem. 50, 4669 (2007)

    Article  CAS  Google Scholar 

  6. 6.

    P.B. Alper, T.H. Marsilje, D. Mutnick, W. Lu, A. Chatterjee, M.J. Roberts, Y. He, D.S. Karanewsky, D. Chow, J. Lao Bioorg. Med. Chem. Lett. 18, 5255 (2008)

    Article  CAS  Google Scholar 

  7. 7.

    U. Pindur, T. Lemster, Recent Res. Devel. Org. Bioorg. Chem 1, 33 (1997)

    CAS  Google Scholar 

  8. 8.

    H.-J. Knölker, K.R. Reddy, Chem. Rev. 102, 4303 (2002)

    Article  CAS  Google Scholar 

  9. 9.

    M. Prudhomme, Curr. Med. Chem. Anti Cancer Agents 4, 509 (2004)

    Article  CAS  Google Scholar 

  10. 10.

    S. Oishi, T. Watanabe, J.-i Sawada, A. Asai, H. Ohno, N. Fujii, J. Med. Chem. 53, 5054 (2010)

    Article  CAS  Google Scholar 

  11. 11.

    Y.-Q. Wang, X.-H. Li, Q. He, Y. Chen, Y.-Y. Xie, J. Ding, Z.-H. Miao, C.-H. Yang, Eur. J. Med. Chem. 46, 5878 (2011)

    Article  CAS  Google Scholar 

  12. 12.

    D. Zhu, M. Chen, M. Li, B. Luo, Y. Zhao, P. Huang, S. Xue, R. Rapposelli, R. Pi, S. Wen, Eur. J. Med. Chem. 68, 81 (2013)

    Article  CAS  Google Scholar 

  13. 13.

    C. Saturnino, D. Iacopetta, M.S. Sinicropi, C. Rosano, A. Caruso, A. Caporale, N. Marra, B. Marengo, M.A. Pronzato, O.I. Parisi, Molecules 19, 9307 (2014)

    Article  CAS  Google Scholar 

  14. 14.

    A. Segall, M. Vitale, V. Perez, M. Pizzorno, J. Pharm. Biomed. Anal. 31, 1021 (2003)

    Article  CAS  Google Scholar 

  15. 15.

    E. Von Angerer, J. Prekajac, J. Med. Chem. 29, 380 (1986)

    Article  Google Scholar 

  16. 16.

    E. Conchon, F. Anizon, B. Aboab, R.M. Golsteyn, S. Léonce, B. Pfeiffer, M. Prudhomme, Biorg. Med. Chem. 16, 4419 (2008)

    Article  CAS  Google Scholar 

  17. 17.

    I.K. Moon, J.-W. Oh, N. Kim, J. Photochem. Photobiol. A Chem. 194, 351 (2008)

    Article  CAS  Google Scholar 

  18. 18.

    N.-X. Hu, S. Xie, Z. Popovic, B. Ong, A.-M. Hor, S. Wang, J. Am. Chem. Soc. 121, 5097 (1999)

    Article  CAS  Google Scholar 

  19. 19.

    H.-P. Zhao, X.-T. Tao, F.-Z. Wang, Y. Ren, X.-Q. Sun, J.-X. Yang, Y.-X. Yan, D.-C. Zou, X. Zhao, M.-H. Jiang, Chem. Phys. Lett. 439, 132 (2007)

    Article  CAS  Google Scholar 

  20. 20.

    Y. Nagase, H. Shirai, M. Kaneko, E. Shirakawa, T. Tsuchimoto, Org. Biomol. Chem. 11, 1456 (2013)

    Article  CAS  Google Scholar 

  21. 21.

    C. Wang, H. Dong, W. Hu, Y. Liu, D. Zhu, Chem. Rev. 112, 2208 (2012)

    Article  CAS  Google Scholar 

  22. 22.

    S. Lengvinaite, J. Grazulevicius, S. Grigalevicius, R. Gu, W. Dehaen, V. Jankauskas, B. Zhang, Z. Xie, Dyes. Pigm. 85, 183 (2010)

    Article  CAS  Google Scholar 

  23. 23.

    M. Kirkus, J. Simokaitiene, J. Grazulevicius, V. Jankauskas, Synth. Met. 160, 750 (2010)

    Article  CAS  Google Scholar 

  24. 24.

    S. Wakim, J. Bouchard, M. Simard, N. Drolet, Y. Tao, M. Leclerc, Chem. Mater. 16, 4386 (2004)

    Article  CAS  Google Scholar 

  25. 25.

    P.-L.T. Boudreault, A.A. Virkar, Z. Bao, M. Leclerc, Org. Electron. 11, 1649 (2010)

    Article  CAS  Google Scholar 

  26. 26.

    Y. Wu, Y. Li, S. Gardner, B.S. Ong, J. Am. Chem. Soc. 127, 614 (2005)

    Article  CAS  Google Scholar 

  27. 27.

    N. Blouin, A. Michaud, S. Wakim, P.L.T. Boudreault, M. Leclerc, B. Vercelli, S. Zecchin, G. Zotti, Macromol. Chem. Phys. 207, 166 (2006)

    Article  CAS  Google Scholar 

  28. 28.

    R. G. Harvey, Polycyclic aromatic hydrocarbons: chemistry and carcinogenicity, CUP Archive1991

  29. 29.

    J.T. Kuethe, K.G. Childers, Adv. Synth. Catal. 350, 1577 (2008)

    Article  CAS  Google Scholar 

  30. 30.

    E. Conchon, F. Anizon, B. Aboab, M. Prudhomme, Synthesis 16, 2569 (2008)

    Google Scholar 

  31. 31.

    T. Tsuchimoto, H. Matsubayashi, M. Kaneko, E. Shirakawa, Y. Kawakami, Angew. Chem. Int. Ed. 44, 1336 (2005)

    Article  CAS  Google Scholar 

  32. 32.

    F. Dufour, G. Kirsch, Synlett 2006, 1021 (2006)

    Article  CAS  Google Scholar 

  33. 33.

    K. Tanaka, Transition-Metal-Mediated Aromatic Ring Construction (Wiley, Hoboken, 2013)

    Google Scholar 

  34. 34.

    F. Jafarpour, H. Hazrati, Adv. Synth. Catal. 352, 363 (2010)

    Article  CAS  Google Scholar 

  35. 35.

    W. Harris, C.H. Hill, E. Keech, P. Malsher, Tetrahedron Lett. 34, 8361 (1993)

    Article  CAS  Google Scholar 

  36. 36.

    C.B. de Koning, J.P. Michael, A.L. Rousseau, Tetrahedron Lett. 39, 8725 (1998)

    Article  Google Scholar 

  37. 37.

    Z. Shi, S. Ding, Y. Cui, N. Jiao, Angew. Chem. 121, 8035 (2009)

    Article  Google Scholar 

  38. 38.

    K. Hirano, Y. Inaba, T. Watanabe, S. Oishi, N. Fujii, H. Ohno, Adv. Synth. Catal. 352, 368 (2010)

    Article  CAS  Google Scholar 

  39. 39.

    X. Cai, V. Snieckus, Org. Lett. 6, 2293 (2004)

    Article  CAS  Google Scholar 

  40. 40.

    J. Yang, Q. Zhang, W. Zhang, W. Yu, RSC Advances 4, 13704 (2014)

    Article  CAS  Google Scholar 

  41. 41.

    E. Kianmehr, M. Ghanbari, N. Faghih, F. Rominger, Tetrahedron Lett. 53, 1900 (2012)

    Article  CAS  Google Scholar 

  42. 42.

    E. Kianmehr, A. Rajabi, M. Ghanbari, Tetrahedron Lett. 50, 1687 (2009)

    Article  CAS  Google Scholar 

  43. 43.

    K. Jadidi, R. Ghahremanzadeh, M. Mehrdad, M. Ghanbari, H. Arvin-Nezhad, Monatsh. Chem. 139, 277 (2008)

    Article  CAS  Google Scholar 

  44. 44.

    E. Kianmehr, N.S. Zafarghandi, M. Ghanbari, Mol. Divers. 17, 383 (2013)

    Article  CAS  Google Scholar 

  45. 45.

    A.S.K. Hashmi, M. Ghanbari, M. Rudolph, F. Rominger, Chem. Eur. J. 18, 8113 (2012)

    Article  CAS  Google Scholar 

  46. 46.

    E. Kianmehr, M. Ghanbari, M.N. Niri, R. Faramarzi, J. Comb. Chem. 12, 41 (2009)

    Article  CAS  Google Scholar 

  47. 47.

    E. Kianmehr, M. Ghanbari, Eur. J. Org. Chem. 2012, 256 (2012)

    Article  CAS  Google Scholar 

  48. 48.

    CCDC-1040369 (8a) contains the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre. www.ccdc.cam.ac.uk/data_request/cif

  49. 49.

    M. Viji, S.K. Ghosh, R. Nagarajan, Synthesis 46, 955 (2014)

    Article  CAS  Google Scholar 

  50. 50.

    B.S. Lane, M.A. Brown, D. Sames, J. Am. Chem. Soc. 127, 8050 (2005)

    Article  CAS  Google Scholar 

  51. 51.

    X. Wang, D.V. Gribkov, D. Sames, J. Org. Chem. 72, 1476 (2007)

    Article  CAS  Google Scholar 

  52. 52.

    D.J. Cárdenas, B. Martín-Matute, A.M. Echavarren, J. Am. Chem. Soc. 128, 5033 (2006)

    Article  CAS  Google Scholar 

  53. 53.

    CCDC-1040370 (11) contains the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre. www.ccdc.cam.ac.uk/data_request/cif

  54. 54.

    S. Fioravanti, L. Pellacani, P.A. Tardella, M.C. Vergari, Org. Lett. 10, 1449 (2008)

    Article  CAS  Google Scholar 

  55. 55.

    A.T.R. William, S.A. Winfield, J.N. Miller, Analyst 108, 1067 (1983)

    Article  Google Scholar 

  56. 56.

    W. Melhuish, J. Phys. Chem. 65, 229 (1961)

    Article  CAS  Google Scholar 

  57. 57.

    W. Rettig, M. Zander, Chem. Phys. Lett. 87, 229 (1982)

    Article  CAS  Google Scholar 

  58. 58.

    A. Kapturkiewicz, J. Herbich, J. Karpiuk, J. Nowacki, J. Phys. Chem. A 101(12), 2332–2344 (1997)

    Article  CAS  Google Scholar 

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Acknowledgments

We gratefully acknowledge financial support from the Research Council of the University of Tehran and University of Kashan. Professor Seik Weng Ng gratefully acknowledges grant number UM.C/625/1/HIR/247 from University of Malaya. We thank Professor A. Stephen K. Hashmi and Dr. Ben A. Coombs, Organisch-Chemisches Institute, University of Heidelberg, for providing access to instrumental facilities for photophysical properties and some chemicals.

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Correspondence to Mohammad Ghanbari or Ebrahim Kianmehr.

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Ghanbari, M., Kianmehr, E., Karimi Behzad, S. et al. Direct synthesis of benzo[a]carbazoles by palladium-catalyzed domino reactions: synthesis and photophysical properties of diverse benzo[a]carbazoles. J IRAN CHEM SOC 13, 7–18 (2016). https://doi.org/10.1007/s13738-015-0706-9

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Keywords

  • Homogeneous catalysis
  • C–C coupling
  • Palladium
  • Photophysical properties
  • Quantum yield