Skip to main content
Log in

Catalytic methods of creation and functionalization of the coumarin skeleton

  • Published:
Chemistry of Heterocyclic Compounds Aims and scope

Methods of synthesis and functionalization of coumarins using metal complex and organic catalysis are considered in the review.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Similar content being viewed by others

References

  1. A. Vogel, Gilbert’s Ann. Phys., 64, 161 (1820).

    Google Scholar 

  2. R. O’Kennedy and R. D. Thornes (editors), Coumarins, Biology, Applications and Mode of Action, John Wiley and Sons, Chichester (1997), p. 348.

    Google Scholar 

  3. J. R. S. Hoult and M. Paya, Gen. Pharmacol., 27, 713 (1996).

    Article  CAS  Google Scholar 

  4. H. Kobayashi, M. Ogawa, R. Alford, P. L. Choyke, and Y. Urano, Chem. Rev., 110, 2620 (2010).

    Article  CAS  Google Scholar 

  5. R. D. H. Murray, J. Mendez, and S. A. Brown, The Natural Coumarins, Occurrence and Biochemistry, John Wiley and Sons, Chichester (1982).

    Google Scholar 

  6. R. D. H. Murray, Prog. Chem. Org. Nat. Prod., 58, 83 (1991).

    CAS  Google Scholar 

  7. R. D. H. Murray, Natl. Prod. Rep., 12, 477 (1995).

    Article  CAS  Google Scholar 

  8. A. Estévez-Braun and A. G. Gonzalez, Nat. Prod. Rep., 14, 465 (1997).

    Article  Google Scholar 

  9. V. M. Malikov and A. I. Saidkhodzhaev, Chem. Nat. Compd., 34, 202 (1998).

    Article  CAS  Google Scholar 

  10. S. Sardari, S. Nishibe, and M. Daneshtalab, Stud. Nat. Prod. Chem., 23, 335 (2000).

    Article  CAS  Google Scholar 

  11. F. Borges, F. Roleira, N. Milhazes, L. Santana, and E. Uriarte, Curr. Med. Chem., 12, 887 (2005).

    Article  CAS  Google Scholar 

  12. M. E. Riveiro, N. De Kimpe, A. Moglioni, R. Vazquez, F. Monczor, C. Shayo, and C. Davio, Curr. Med. Chem., 17, 1325 (2010).

    Article  CAS  Google Scholar 

  13. M. M. Garazd, Y. L. Garazd, and V. P. Khilya, Chem. Nat. Compd., 41, 245 (2005).

    Article  CAS  Google Scholar 

  14. G. Volmajer, R. Toplak, I. Leban, and A. Majcen Le Marechal, Tetrahedron, 61, 7012 (2005).

    Article  CAS  Google Scholar 

  15. V. K. Ahluwalia, D. Singh, and R. P. Singh, Monatsh. Chem., 116, 869 (1985).

    Article  CAS  Google Scholar 

  16. E. Rizzi, S. Dallavalle, L. Merlini, G. Pratesi, and F. Zunino, Synth. Commun., 36, 1117 (2006).

    Article  CAS  Google Scholar 

  17. K. Sato and T. Amakasu, J. Org. Chem., 33, 2446 (1968).

    Article  CAS  Google Scholar 

  18. J. R. Bantick and J. L. Suschitzky, J. Heterocycl. Chem., 18, 679 (1981).

    Article  CAS  Google Scholar 

  19. B. M. Trost and F. D. Toste, J. Am. Chem. Soc., 118, 6305 (1996).

    Article  CAS  Google Scholar 

  20. C. Jia, W. Lu, J. Oyamada, T. Kitamura, K. Matsuda, M. Irie, Y. Fujiwara, J. Am. Chem. Soc., 122, 7252 (2000).

    Article  CAS  Google Scholar 

  21. C. Jia, D. Piao, J. Oyamada, W. Lu, T. Kitamura, and Y. Fujiwara, Science, 287, 1992 (2000).

    Article  CAS  Google Scholar 

  22. S. Aoki, J. Oyamada, and T. Kitamura, Bull. Chem. Soc. Japan, 78, 468 (2005).

    Article  CAS  Google Scholar 

  23. S. Aoki, C. Amamoto, J. Oyamada, and T. Kitamura, Tetrahedron, 61, 9291 (2005).

    Article  CAS  Google Scholar 

  24. C. Jia, D. Piao, T. Kitamura, and Y. Fujiwara, J. Org. Chem., 65, 7516 (2000).

    Article  CAS  Google Scholar 

  25. S. J. Pastine, S. W. Youn, and D. Sames, Org. Lett., 5, 1055 (2003).

    Article  CAS  Google Scholar 

  26. K. H. Park, I. G. Jung, and Y. K. Chung, Synlett, 2541 (2004).

  27. Y. Yamamoto and N. Kirai, Org. Lett., 10, 5513 (2008).

    Article  CAS  Google Scholar 

  28. X. Han and X. Lu, Org. Lett., 12, 108 (2010).

    Article  Google Scholar 

  29. M. Catellani, G. P. Chiusoli, G. Marzolini, and E. Rossi, J. Organomet. Chem., 525, 65 (1996).

    Article  CAS  Google Scholar 

  30. T. Meng, Y. Zou, O. Khorev, Y. Jin, H. Zhou, Y. Zhang, D. Hu, L. Ma, X. Wang, and J. Shen, Adv. Synth. Cat., 353, 918 (2011).

    Article  CAS  Google Scholar 

  31. D. V. Kadnikov and R. C. Larock, J. Org. Chem., 68, 9423 (2003).

    Article  CAS  Google Scholar 

  32. D. V. Kadnikov and R. C. Larock, Org. Lett. 23, 3643 (2000).

    Article  Google Scholar 

  33. A. K. Chatterjee, F. D. Toste, S. D. Goldberg, and R. H. Grubbs, Pure Appl. Chem., 75, 421 (2003).

    Article  CAS  Google Scholar 

  34. T. N. Van, S. Debenedetti, and N. De Kimpe, Tetrahedron Lett., 44, 4199 (2003).

    Article  Google Scholar 

  35. U. Gross, P. J. Gross, M. Shi, and S. Bräse, Synlett, 635 (2011).

  36. G. M. Boland, D. M. X. Donnelly, J.-P. Finet, and M. D. Rea, J. Chem. Soc., Perkin Trans 1, 2591 (1996).

  37. C. Bailly, C. Bal, P. Barbier, S. Combes, J.-P Finet, M.-P. Hildebrand, V. Peyrot, and N. Wattez, J. Med. Chem., 46, 5437 (2003).

    Article  CAS  Google Scholar 

  38. D. M. X. Donnelly, J.-P. Finet, P. J. Guiry, and M. D. Rea, Synth. Commun., 29, 2719 (1999).

    Article  CAS  Google Scholar 

  39. I. P. Beletskaya, O. G. Ganina, A. V. Tsvetkov, A. Yu. Fedorov, and J.-P. Finet, Synlett, 2797 (2004).

  40. O. G. Ganina, E. Daras, V. Bourgarel-Rey, V. Peyrot, A. N. Andresyuk, J.-P. Finet, A. Yu. Fedorov, I. P. Beletskaya, and S. Combes, Bioorg. Med. Chem., 16, 8806 (2998).

  41. M. I. Naumov, A. V. Nuchev, N. S. Sitnikov, Yu. B. Malysheva, A. S. Shavyrin, I. P. Beletskaya, A. E. Gavryushin, S. Combes, and A. Yu. Fedorov, Synthesis, 1673 (2009).

  42. N. S. Sitnikov, A. S. Shavyrin, G. K. Fukin, I. P. Beletskaya, S. Combes, and A. Yu. Fedorov, Izv. Akad. Nauk, Ser. Khim., 3, 612 (2010). [Russ. Chem. Bull., 59, 626 (2010)].

    Google Scholar 

  43. S. Combes, P. Barbier, S. Douillard, A. McLeer-Florin, V. Bourgarel-Rey, J.-T. Pierson, A. Yu. Fedorov, J.-P. Finet, J. Boutonnat, and V. Peyrot, J. Med. Chem., 54, 3153 (2011).

    Article  CAS  Google Scholar 

  44. Y. Luo and J. Wu, Tetrahedron Lett., 50, 2103 (2009).

    Article  CAS  Google Scholar 

  45. A. N. Selikhov, Yu. B. Malysheva, A. V. Nyuchev, N. S. Sitnikov, E. A. Sharonova, A. S. Shavyrin, S. Combes, and A. Yu. Fedorov, Izv. Akad. Nauk, Ser. Khim., 1968 (2011).

  46. H. Guo, E. Herdtweck, and T. Bach, Angew. Chem., Int. Ed., 49, 7782 (2010).

    Article  CAS  Google Scholar 

  47. A. V. Nyuchev, E. A. Sharonova, N. A. Lenshina, A. S. Shavyrin, M. A. Lopatin, I. V. Balalaeva, I. P. Beletskaya, and A. Yu. Fedorov, Tetrahedron Lett., 52, 4196 (2011).

    Article  CAS  Google Scholar 

  48. Y. Luo and J. Wu, Tetrahedron, 65, 6810 (2009).

    Article  CAS  Google Scholar 

  49. J. A. Key, S. Koh, Q. K. Timerghazin, A. Brown, and C. W. Cairo, Dyes Pigm., 82, 196 (2009).

    Article  CAS  Google Scholar 

  50. S. Valente and G. Kirsch, Tetrahedron Lett., 52, 3429 (2011).

    Article  CAS  Google Scholar 

  51. S. Martins, P. S. Branco, M. C. de la Torre, M. A. Sierra, and A. Pereira, Synlett, 2918 (2010).

  52. A. R. Das, A. Medda, and R. Singha, Tetrahedron Lett., 51, 1099 (2010).

    Article  CAS  Google Scholar 

  53. D. Audisio, S. Messaoudi, J.-F. Peyrat, J.-D. Brion, and M. Alami, Tetrahedron Lett., 48, 6928 (2007).

    Article  CAS  Google Scholar 

  54. O. Ganina, A. Yu. Fedorov, and I. P. Beletskaya, Synthesis, 3689 (2009).

  55. L. Zhang, T. Meng, R. Fan, and J. Wu, J. Org. Chem., 72, 7279 (2007).

    Article  CAS  Google Scholar 

  56. S. H. Wunderlich and P. Knochel, Angew. Chem., Int. Ed., 46, 7685 (2007).

    Article  CAS  Google Scholar 

  57. R. D. Rieke and S.-H. Kim, Tetrahedron Lett., 52, 3094 (2011).

    Article  CAS  Google Scholar 

  58. F. Gosselin, R. A. Britton, I. W. Davies, S. J. Dolman, D. Gauvreau, R. S. Hoerrner, G. Hughes, J. Janey, S. Lau, C. Molinaro, C. Nadeau, P. D. O'Shea, M. Palucki, and R. Sidler, J. Org. Chem., 75, 4154 (2010).

    Article  CAS  Google Scholar 

  59. K. Sivakumar, F. Xie, B. M. Cash, S. Long, H. N. Barnhill, and Q. Wang, Org. Lett., 6, 4603 (2004).

    Article  CAS  Google Scholar 

  60. X.-P. He, Z. Song, Z.-Z. Wang, X.-X. Shi, K. Chen, and G.-R. Chen, Tetrahedron, 67, 3343 (2011).

    Article  CAS  Google Scholar 

  61. F. Seela, V. R. Sirivolu, and P. Chittepu, Bioconjugate Chem., 19, 211 (2008).

    Article  CAS  Google Scholar 

  62. Y. Zhou, K. Liu, J.-Y. Li, Y. Fang, T.-C. Zhao, and C. Yao, Org. Lett., 13, 1290 (2011).

    Article  CAS  Google Scholar 

  63. J. C. Morris, J. C. McMurtrie, S. E. Bottle, and K. E. Fairfull-Smith, J. Org. Chem., 76, 4964 (2011).

    Article  CAS  Google Scholar 

  64. J. Lu, M. Shi, and M. S. Shoichet, Bioconjugate Chem., 20, 87 (2009).

    Article  Google Scholar 

  65. P. Chittepu, V. R. Sirivolu, and F. Seela, Bioorg. Med. Chem., 16, 8427 (2008).

    Article  CAS  Google Scholar 

  66. N. Anand, N. Jaiswal, S. K. Pandey, A. K. Srivastava, and R. P. Tripathi, Carbohydr. Res., 346, 16 (2011).

    Article  CAS  Google Scholar 

  67. A. V. Nyuchev, E. A. Sharonova, N. A. Lenshina, A. S. Shavyrin, M. A. Lopatin, I. V. Balalaeva, I. P. Beletskaya, and A. Yu. Fedorov, Tetrahedron Lett., 52, 4196 (2011).

    Article  CAS  Google Scholar 

  68. X. Zhu, A. Lin, Y. Shi, J. Guo, C. Zhu, and Y. Cheng, Org. Lett., 13, 4382 (2011).

    Article  CAS  Google Scholar 

  69. H.-M. Yang, L. Li, K.-Z. Jiang, J.-X. Jiang, G.-Q. Lai, and L.-W. Xu, Tetrahedron, 66, 9708 (2010).

    Article  CAS  Google Scholar 

  70. K. C. Majumdar, R. K. Nandi, S. Samanta, and B. Chattopadhyay, Synthesis, 6, 985 (2010).

    Article  Google Scholar 

  71. K. C. Majumdar, B. Chattopadhyay, and S. Nath, Tetrahedron Lett., 49, 1609 (2008).

    Article  CAS  Google Scholar 

  72. L. Chen and M.-H. Xu, Adv. Synth. Catal., 351, 2005 (2009).

    Article  CAS  Google Scholar 

  73. R. V. Rozhkov and R. C. Larock, Org. Lett., 5, 797 (2003).

    Article  CAS  Google Scholar 

  74. L.-P. Fan, P. Li, X.-S. Li, D.-C. Xu, M.-M. Ge, W.-D. Zhu, and J.-W. Xie, J. Org. Chem., 75, 8716 (2010).

    Article  CAS  Google Scholar 

  75. L. Chen, Y. Li, and M.-H. Xu, Org. Biomol. Chem., 8, 3073 (2010).

    Article  CAS  Google Scholar 

  76. L. Tang, Y. Pang, Q. Yan, L. Shi, J. Huang, Y. Du, and K. Zhao, J. Org. Chem., 76, 2744 (2011).

    Article  CAS  Google Scholar 

  77. J. Padwal, W. Lewis, and C. J. Moody, Synlett, 514 (2010).

  78. M. Rueping, E. Merino, and E. Sugiono, Adv. Synth. Catal., 350, 2127 (2008).

    Article  CAS  Google Scholar 

  79. Y. Gao, Q. Ren, L. Wang, and J. Wang, Chem. Eur. J., 16, 13068 (2010).

    Article  CAS  Google Scholar 

  80. H. Zhao, A. C. Donnelly, B. R. Kusuma, G. E. L. Brandt, D. Brown, R. A. Rajewski, G. Vielhauer, J. Holzbeierlein, M. S. Cohen, and B. S. J. Blagg, J. Med. Chem., 54, 3839 (2011).

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to A. Yu. Fedorov.

Additional information

Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 1, pp. 175-186, January, 2012.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Fedorov, A.Y., Nyuchev, A.V. & Beletskaya, I.P. Catalytic methods of creation and functionalization of the coumarin skeleton. Chem Heterocycl Comp 48, 166–178 (2012). https://doi.org/10.1007/s10593-012-0980-8

Download citation

  • Received:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10593-012-0980-8

Keywords

Navigation