Skip to main content
SpringerLink
Log in

Methods for the construction of [1,2]isoindolo-condensed benzazepines, benzazocines, quinolines, and isoquinolines. 1. Isoindolobenzazepines, isoindolobenzazocines. (Review)

  • Published:
Chemistry of Heterocyclic Compounds Aims and scope

Abstract

Data on methods for the construction of tetracyclic systems in which an isoindole ring is condensed with benzazepines and benzazocines on the [1,2] side are reviewed. The reaction conditions and approaches leading to isoindolobenzazepines and isoindolobenzazocines are discussed. Examples of the synthesis of physiologically active natural alkaloids with the structure of the above-mentioned condensed isoindoles are presented. Data for 1959–2004 are included.

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

Access this article

Log in via an institution

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

Instant access to the full article PDF.

Institutional subscriptions

Similar content being viewed by others

References

  1. P. Pigeon and B. Decroix, Synth. Commun., 28, 2507 (1998).

    CAS  Google Scholar 

  2. G. N. Walker, A. R. Engle, and R. J. Kempton, J. Org. Chem., 37, 3755 (1972).

    Article  CAS  Google Scholar 

  3. H. Heaney and K. F, Shuhaibar, Synlett, 47 (1995).

  4. M. T. El Gihani, H. Heaney, and K. F. Shuhaibar, Synlett, 871 (1996).

  5. P. Pigeon and B. Decroix, Tetrahedron Lett., 38, 1041 (1997).

    Article  CAS  Google Scholar 

  6. Y. Ishihara, Y. Kiyota, and G. Goto, Chem. Pharm. Bull., 38, 3024 (1990).

    CAS  Google Scholar 

  7. A. Dalch, S. Marchalin, P. Pigeon, and B. Decroix, Tetrahedron Lett., 39, 9187 (1998).

    Article  Google Scholar 

  8. Y. Ishihara, T. Tanaka, S. Miwatashi, A. Fujishima, and G. Goto, J. Chem. Soc., Perkin Trans. 1, 2993 (1994).

  9. A. Chihab-Eddine, A. Daich, A. Wale, and B. Decroix, Heterocycles, 58, 449 (2002).

    CAS  Google Scholar 

  10. Y. Ishihara, T. Doi, H. Nagabukuro, and Y. Ishichi, WO Pat. 00/18391; http://v3.espacenet.com/origdoc?DB=EPODOC&IDX=WO0018391&F=0&QPN=WO00183 91

  11. Y. Ishihara, Y. Fujisawa, and N. Furuyama, WO Pat. 9846590; Chem. Abstr., 129, 330744 (1998).

  12. G. Goto, Y. Ishihara, and M. Miyamoto, EP Pat. 655451; Chem. Abstr., 123, 198832 (1995).

  13. G. Goto and Y. Ishihara, Jpn. Pat. 02042078; Chem. Abstr., 113, 40431 (1990).

    Google Scholar 

  14. C. Schöpf and M. Schweickert, Chem. Ber., 99, 2566 (1965).

    Google Scholar 

  15. E. Valencia, I. Weiss, S. Firdous, A. J. Freyer, M. Shamma, A. Urzsa, and V. Fajardo, Tetrahedron, 40, 3957 (1984).

    Article  CAS  Google Scholar 

  16. V. Fajardo, V. Elango, B. K. Cassels, and M. Shamma, Tetrahedron Lett., 23, 39 (1982).

    Article  CAS  Google Scholar 

  17. E. Valencia, A. J. Freyer, M. Shamma, and V. Fajardo, Tetrahedron Lett., 25, 599 (1984).

    Article  CAS  Google Scholar 

  18. J. Fuska, A. Fuskovi, and B. Proksa, Pharmazie, 37, 443 (1982).

    CAS  Google Scholar 

  19. B. Proksa and J. Fuska, Pharmazie, 40, 521 (1985).

    CAS  Google Scholar 

  20. V. Scartoni, R. Fiaschi, S. Catalano, I. Morelli, and A. Marsili, J. Chem. Soc., Perkin Trans. 1, 1547 (1979).

  21. P. L. Barili, R. Fiaschi, E. Napolitano, L. Pistelli, V. Scartoni, and A. Marsili, J. Chem. Soc., Perkin Trans. 1, 1654 (1981).

  22. E. Napolitano, R. Fiaschi, V. Scartoni, and A. Marsili, J. Chem. Soc., Perkin Trans. 1, 781 (1986).

  23. E. Napolitano, G. Spinelli, R. Fiaschi, and A. Marsili, J. Chem. Soc., Perkin Trans. 1, 785 (1986).

  24. A. Couture, E. Deniau, P. Grandclaudon, and C. Hoarau, Tetrahedron, 56, 1491 (2000).

    Article  CAS  Google Scholar 

  25. Y. Koseki and T. Nagasaka, Chem. Pharm. Bull., 43, 1604 (1995).

    CAS  Google Scholar 

  26. A. Marsili, V. Scartoni, I. Morelli, and P. Pierangeli, J. Chem. Soc., Perkin Trans. 1, 959 (1977).

  27. H. O. Bernhard and V. Snieckus, Tetrahedron Lett., 4867 (1971).

  28. G. Kim, J. H. Kim, W.-J. Kim, and Y. A. Kim, Tetrahedron Lett., 44, 8207 (2003).

    Article  CAS  Google Scholar 

  29. G. Rodriguez, M. M. Cid, C. Sai, L. Castedo, and D. Dominguez, J. Org. Chem., 61, 2780 (1996).

    Article  CAS  Google Scholar 

  30. M. M. Cid, D. Domknguez, L. Castedo, E. M. Vizquez-Lopez, Tetrahedron, 55, 5599 (1999).

    Article  CAS  Google Scholar 

  31. H. Yoda, A. Nakahama, T. Koketsu, and K. Takabe, Tetrahedron Lett., 43, 4667 (2002).

    Article  CAS  Google Scholar 

  32. P. H. Mazzocchi, C. R. King, and H. L. Amnion, Tetrahedron Lett., 28, 2473 (1987).

    Article  CAS  Google Scholar 

  33. M. Machida, M. Nakamura, K. Oda, H. Takechi, K. Ohno, H. Nakai, Y. Sato, and Y. Kanaoka, Heterocycles, 26, 2683 (1987).

    CAS  Google Scholar 

  34. H. Ishibashi, H. Kawanami, H. Iriyama, and M. Ikeda, Tetrahedron Lett., 36, 6733 (1995).

    CAS  Google Scholar 

  35. H. Ishibashi, H. Kawanami, and M. Ikeda, J. Chem. Soc., Perkin Trans. 1, 817 (1997).

  36. J. Trojanek, Z. Koblicova, V. Suchan, and J. Holubek, Collect. Czech. Chem. Commun., 40, 681 (1975).

    CAS  Google Scholar 

  37. B. Proksa, Z. Votickz, and M. Stefek, Chem. Zvesti, 34, 248 (1980).

    CAS  Google Scholar 

  38. B. Proska, J. Fuska, Z. Voticky, Pharmazie, 37, 350 (1982).

    CAS  Google Scholar 

  39. A. Garcia, D. Rodriguez, L. Castedo, C. Sai, and D. Dominguez, Tetrahedron Lett., 42, 1903 (2001).

    Article  CAS  Google Scholar 

  40. S. Ruchirawat, W. Lertwanawatana, S. Thianpatanagul, J. L. Cashaw, and V. E. Davis, Tetrahedron Lett., 25, 3485 (1984).

    Article  CAS  Google Scholar 

  41. J. Chiefari, W. K. Janowski, and R. H. Prager, Tetrahedron Lett., 27, 6119 (1986).

    Article  CAS  Google Scholar 

  42. J. Chiefari, W. K. Janowski, and R. H. Prager, Aust. J. Chem., 42, 49 (1989).

    Article  CAS  Google Scholar 

  43. S. V. Kessar, T. Singh, and R. Vohra, Tetrahedron Lett., 28, 5323 (1987).

    Article  CAS  Google Scholar 

  44. S. V. Kessar, T. Singh, and R. Vohra, Ind. J. Chem., 30B, 99 (1991).

    Google Scholar 

  45. F. G. Fang and S. J. Danishefsky, Tetrahedron Lett., 30, 2747 (1989).

    Article  CAS  Google Scholar 

  46. S. Ruchirawat and P. Sahakitpichan, Tetrahedron Lett., 41, 8007 (2000).

    Article  CAS  Google Scholar 

  47. W. Klötzer, S. Teitel, J. F. Blount, and A. Brossi, J. Am. Chem. Soc., 93, 4321 (1971).

    Article  Google Scholar 

  48. W. Klötzer, S. Teitel, and A. Brossi, Helv. Chim. Acta, 54, 2057 (1971).

    Article  Google Scholar 

  49. R. Hohlbrugger, W. Klötzer, Chem. Ber., 107, 3457 (1974).

    CAS  Google Scholar 

  50. S. Teitel, W. Klötzer, J. Borgese, and A. Brossi, Can. J. Chem., 50, 2022 (1972).

    Article  CAS  Google Scholar 

  51. C. J. Moody and G. J. Warrellow, J. Chem. Soc., Perkin Trans. 1, 2929 (1990).

  52. C. J. Moody and G. J. Warrellow, Tetrahedron Lett., 28, 6089 (1987).

    Article  CAS  Google Scholar 

  53. S. Yasuda, Y.-I. Sugimoto, C. Mukai, and M. Hanaoka, Heterocycles, 30, 335 (1990).

    Article  CAS  Google Scholar 

  54. J. R. Fuchs and R. L. Funk, Org. Lett., 3, 3923 (2001).

    Article  CAS  Google Scholar 

  55. D. Walterova and F. Santava, Collect. Czech. Chem. Commun., 35, 1623 (1968).

    Google Scholar 

  56. M. Shamma, The Isoquinoline Alkaloids, Academic Press, New York (1972).

    Google Scholar 

  57. J. L. Moniot, D. M. Hindenlang, and M. Shamma, J. Org. Chem., 44, 4343 (1979).

    Article  CAS  Google Scholar 

  58. G. Manikumar and M. Shamma, Heterocycles, 14, 827 (1980).

    Article  CAS  Google Scholar 

  59. C. K. Dorn, F. J. Koszyk, and G. R. Lenz, J. Org. Chem., 49, 2642 (1984).

    Article  Google Scholar 

  60. J. L. Moniot, D. M. Hindenlang, and M. Shamma, J. Org. Chem., 44, 4347 (1979).

    Article  CAS  Google Scholar 

  61. M. Shamma, J. L. Moniot, and D. M. Hindenlang, Tetrahedron Lett., 4273 (1977).

  62. V. Elango and M. Shamma, J. Org. Chem., 48, 4879 (1983).

    Article  CAS  Google Scholar 

  63. C. Lamas, C. Saa, L. Castedo, and D. Domknguez, Tetrahedron Lett., 33, 5653 (1992).

    Article  CAS  Google Scholar 

  64. G. Rodrkguez, L. Castedo, D. Domknguez, and C. Sai, Tetrahedron Lett., 39, 6551 (1998).

    Article  Google Scholar 

  65. G. Rodrkguez, L. Castedo, D. Domknguez, C. Sai, W. Adam, and C. R. Saha-Möller, J. Org. Chem., 64, 877 (1999).

    Article  Google Scholar 

  66. A. Padwa, L. S. Beall, C. K. Eidell, and K. J. Worsencroft, J. Org. Chem., 66, 2414 (2001).

    Article  CAS  Google Scholar 

  67. Y. Koseki, S. Kusano, H. Sakata, and T. Nagasaka, Tetrahedron Lett., 40, 2169 (1999).

    Article  CAS  Google Scholar 

  68. Y. Koseki, S. Katsura, S. Kusano, H. Sakata, H. Sato, Y. Monzene, and T. Nagasaka, Heterocycles, 59, 527 (2003).

    CAS  Google Scholar 

  69. H. Heaney and K. F. Shuhaibar, Tetrahedron Lett., 35, 2751 (1994).

    Article  CAS  Google Scholar 

  70. F. I. Zubkov, E. V. Boltukhina, A. P. Krapivko, and A. V. Varlamov, Khim. Geterotsikl. Soedin., 1737 (2003). [Chem. Heterocycl. Compd., 39, 1534 (2003)]

    Google Scholar 

  71. F. I. Zubkov, E. V. Boltukhina, K. F. Turchin, and A. V. Varlamov, Tetrahedron, 60, 8455 (2004).

    Article  CAS  Google Scholar 

  72. E. Valencia, V. Fajardo, A. J. Freyer, and M. Shamma, Tetrahedron Lett., 26, 993 (1985).

    Article  CAS  Google Scholar 

  73. M. Shamma and M. Rahimizadeh, J. Nat. Prod., 49, 398 (1986).

    Article  CAS  Google Scholar 

  74. R. Yoneda, Y. Sakamoto, Y. Oketo, K. Minami, S. Harusawa, and T. Kurihara, Tetrahedron Lett., 35, 3749 (1994).

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Russian People’s Friendship University, Russia

    E. V. Boltukhina, F. I. Zubkov & A. V. Varlamov

Authors
  1. E. V. Boltukhina
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. F. I. Zubkov
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. A. V. Varlamov
    View author publications

    You can also search for this author in PubMed Google Scholar

Additional information

__________

Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 7, pp. 963–994, July, 2006.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Boltukhina, E.V., Zubkov, F.I. & Varlamov, A.V. Methods for the construction of [1,2]isoindolo-condensed benzazepines, benzazocines, quinolines, and isoquinolines. 1. Isoindolobenzazepines, isoindolobenzazocines. (Review). Chem Heterocycl Compd 42, 831–857 (2006). https://doi.org/10.1007/s10593-006-0169-0

Download citation

  • Received:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10593-006-0169-0

Keywords

Search

Navigation