Skip to main content
Log in

Cyclopenta- and indenopyridine anhydrobases. A review

  • Published:
Chemistry of Heterocyclic Compounds Aims and scope

Abstract

The preparation, structure, spectral characteristics, and chemical transformations of cyclopenta- and indenopyridine anhydrobases are reviewed.

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. M. E. Vol'pin, Usp. Khim.,29, 298 (1960).

    Google Scholar 

  2. H.-J. Timpe and A. V. El'tsov (Elkov) Adv. Heterocycl. Chem.33, 185 (1983).

    Google Scholar 

  3. R. Mayer, Angew. Chem.,69, 481 (1957).

    Google Scholar 

  4. G. V. Boyd, Chem. Ind., No. 37, 1244 (1957).

  5. M. Los, J. P. Saxena, and W. H. Stafford, Proc. Chem. Soc., No. 12, 352 (1957).

  6. G. V. Boyd, J. Chem. Soc., No. 5, 1978 (1958).

  7. W. Treibs and W. Schroth, Ann.,642, 82 (1961).

    Google Scholar 

  8. D. Ginsburg (ed.), Nonbenzoid Aromatic Compounds [Russian translation]. Inos. Lit., Moscow (1963), p. 176.

    Google Scholar 

  9. V. B. Mochalin and Yu. N. Porshnev, Usp. Khim.,46, 1002 (1977).

    Google Scholar 

  10. Yu. M. Porshnev, V. B. Mochalin, and M. I. Cherkashin, Usp. Khim.,51, 1897 (1982).

    Google Scholar 

  11. G. T. Tatevosyan, Anhydronium Carboline Bases [in Russian], Izd. Akad. Nauk ArmSSR, Yerevan (1966).

    Google Scholar 

  12. T. Nishiwaki and N. Abe, Heterocycles,15, 547 (1981).

    Google Scholar 

  13. R. D. Woodward and B. Witkop, J. Am. Chem. Soc.,71, 379 (1949).

    Google Scholar 

  14. N. Hughes and H. Rapoport, J. Am. Chem. Soc.,80, 1604 (1958).

    Google Scholar 

  15. G. Buchi, R. E. Manning, and F. A. Hochsten, J. Am. Chem. Soc.,84, 3393 (1962).

    Google Scholar 

  16. W. Treibs, Naturwiss.49, 37 (1962).

    Google Scholar 

  17. W. Treibs and J. Berger, Ann.,652, 212 (1962).

    Google Scholar 

  18. G. V. Boyd, J. Chem. Soc., No. 1, 55 (1959).

  19. N. S. Prostakov, P. K. Radjan, and A. T. Soldatenkov, Khim. Geterotsikl. Soedin., No. 11, 1516 (1980).

  20. N. S. Prostakov, A. T. Soldatenkov, V. O. Fedorov, S. Mobio, and M. A. Galiullin, Khim. Geterotsikl. Soedin., No. 11, 1511 (1980).

  21. N. S. Prostakov, A. T. Soldatenkov, V. O. Fedorov and P. K. Radjan, Khim. Geterotsikl. Soedin, No. 6, 850 (1980).

  22. N. S. Prostakov, A. T. Soldatenkov, V. O. Fedorov, P. K. Radjan, and M. W. Baghdadi, Abstracts of the Seventh Symposium on the Chemistry of Heterocyclic Compounds, Bratislava, Czechoslovakia (1981), p. 71.

  23. N. S. Prostakov, A. T. Soldatenkov, M. W. Baghdadi, A. A. Fomichev, and N. I. Golovtsov, Khim. Geterotsikl. Soedin., No. 9, 1238 (1982).

  24. N. S. Prostakov, A. T. Soldatenkov, P. K. Radjan, O. P. Kartomasheva, N. G. Rozhkova, and L. I. Valueva, in: Abstracts of the First All-Union Conference Growth Regulators and Plant Development [in Russian]. Moscow (1981), p. 206.

  25. N. S. Prostakov, A. T. Soldatenkov, M. W. Baghdadi, E. I. Andreeva, and S. S. Kukalenko, Abstracts of the All-Union Conference on Plant Pesticides [in Russian], Part 4, Ufa (1982), p. 75.

  26. N. S. Prostakov, S. Keti, N. M. Mikhailova, L. A. Murgova, and V. F. Zakharov, Khim. Geterotsikl. Soedin., No. 10, 1382 (1981).

  27. N. S. Prostakov, A. T. Soldatenkov, P. K. Radjan, V. O. Fedorov, A. A. Formichev, and V. A. Rezakov, Khim. Geterotsikl. Soedin., No. 4, 513 (1982).

  28. J. J. Eisch and G. Gupta, Tetrahedron Lett., No. 32, 3273 (1972).

  29. N. S. Prostakov, L. A. Gaivoronskaya, R. I. Anastasi, S. M. K. Maiga, A. A. Savina, L. A. Murgova, and P. I. Zakharov, Khim. Geterotsikl. Soedin., No. 11, 1514 (1979).

  30. H.-J. Timpe and A. V. El'tsov (Elcov), Z. Chem.,15, 218 (1975).

    Google Scholar 

  31. W. Treibs and J. Berger, Ann.652, 192 (1962).

    Google Scholar 

  32. A. T. Soldatenkov, M. W. Baghdadi, R. M. Romero, A. A. Fomichev, and N. S. Prostakov, Khim. Geterotsikl. Soedin., No. 8, 1108 (1983).

  33. H.-J. Timpe, J. Mlochowski, and Z. Szule, Z. Chem.,19, 374 (1979).

    Google Scholar 

  34. E. M. Evleth, Theor. Chim. Acta,16, 22 (1970).

    Google Scholar 

  35. M. Raimondi and G. Favini, Gazz. Chim. Ital.,98, 433 (1968).

    Google Scholar 

  36. A. G. Anastassiou, E. Reichtnanis, and S. G. Girgenti, J. Am. Chem. Soc.,99, 7392 (1977).

    Google Scholar 

  37. D. Leaver, J. Smolicz, and W. H. Stafford, J. Chem. Soc., No. 3, 740 (1962).

  38. J. J. Eisch, H. Gopal, and C. T. Kuo, J. Org. Chem.43, 2190 (1978).

    Google Scholar 

  39. R. Borsdorf, J. Prakt. Chem.,32, 211 (1966).

    Google Scholar 

  40. P. A. Plattner, A. Furst, M. Gordon, and K. Zimmerman, Helv. Chim. Acta,33, 1910 (1950).

    Google Scholar 

  41. E. Kloster-Yensen, E. Kova, A. Eschenmoser, and E. Heilbroner, Helv. Chim. Acta,39, 1051 (1956).

    Google Scholar 

  42. N. S. Prostakov, A. A. Obynochnyi, and L. A. Murglova, Khim. Geterotsikl. Soedin., No. 5, 657 (1987).

  43. T. V. Stupnikova, B. P. Zemskii, R. S. Sagitullin, and A. N. Kost, Khim. Geterotsikl. Soedin., No. 3, 291 (1982).

  44. W. Treibs, W. Schroth, H. Lichtmann, and G. W. Fischer, Ann.,642, 97 (1961).

    Google Scholar 

  45. W. Treibs, W. F. Harrison, and R. G. Anderson, J. Am. Chem. Soc.,85, 3448 (1963).

    Google Scholar 

  46. J. J. Eisch, F. J. Gadek, and G. Gupta, J. Org. Chem.48, 431 (1973).

    Google Scholar 

  47. A. G. Anastassiou, S. J. Girgenti, R. C. Griffith, and E. Reichtmanis, J. Org. Chem.,42, 2651 (1977).

    Google Scholar 

  48. N. P. Bun-Hoi, A. Croisi, P. Jaquignon, A. Martini, and J. J. Ricci, J. Heterocycl. Chem.,7, 931 (1970).

    Google Scholar 

  49. J. Deutsch, Z. Neiman, and F. Bergmann, Organic Mass Spectr.,5, 279 (1977).

    Google Scholar 

  50. A. A. Fomichev, V. A. Svoren, N. I. Golovtsov, A. T. Soldatenkov, and N. C. Prostakov, Org. Magn. Reson.,19, 24 (1982).

    Google Scholar 

  51. B. F. Malinchenko, Molecular Diagrams of Organic Compounds [in Russian]. Naukova Dumka, Kiev (1982). p. 194.

    Google Scholar 

  52. A. V. El'tsov, G.-I. Timpe and N. I. Rtitsev, Zh. Org. Chem.,11, 398 (1975).

    Google Scholar 

  53. W. Treibs and W. Schroth, Ann.,642, 82 (1961).

    Google Scholar 

  54. N. S. Prostakov, E. V. Kruglyak, V. P. Shalimov, and L. A. Murgova, Khim. Geterotsikl. Soedin., No. 7, 915 (1992).

  55. N. S. Prostakov, B. Montenegro Cordova Galo, and V. P. Shalimov, Khim. Geterotsikl. Soedin., No. 10, 1395 (1985).

  56. C. Jutz, R. M. Wagner, F. Kraatz, and H. Lobering, Ann., No. 5, 874 (1975).

  57. G. Surpateanu, P. Karafilaglu, and A. Lablache-Combier, Tetrahedron,32, 2647 (1976).

    Google Scholar 

  58. I. Zugravescu and M. Petrovani, N-Ylid Chemistry, Bucharest (1976), p. 155.

  59. N. S. Prostakov, A. P. Krapivko, A. T. Soldatenkov, A. A. Savina, and I. Romero, Khim. Geterotsikl. Soedin., No. 3. 384 (1979).

  60. N. S. Prostakov, L. A. Gaivoronskaya, R. Anastasi, S. M. K. Maiga, and A. A. Savina, Khim. Geterotsikl. Soedin., No. 6, 794 (1979).

  61. F. Vog, J. Grutze, R.Natscher, W. Weider, E. Weber, and R. Grun, Chem. Ber.,108, 1694 (1975).

    Google Scholar 

  62. W. Treibs and G. Kempter, Chem. Ber.,92, 601 (1959).

    Google Scholar 

  63. R. Mayer, J. Franke, V. Horak, I. Hanker, and R. Zahradnik, Tetrahedron Lett., No. 9, 289 (1961).

  64. L. E. Kholodov, I. F. Tishchenkova, and V. G. Yashinskii (Yashinskij), Tetrahedron Lett., No. 18, 1535 (1970).

  65. V. N. Gogte, M. A. Salama, and V. O. Tilak, Tetrahedron,26, 173 (1970).

    Google Scholar 

  66. A. G. Anderson and W. F. Harrison, J. Am. Chem. Soc.,86, 708 (1964).

    Google Scholar 

  67. S. S. Daniluk and W. G. Schneider, J. Am. Chem. Soc.,82, 997 (1960).

    Google Scholar 

  68. K. Hafner and M. Kreuder, Angew. Chem.,73, 657 (1961).

    Google Scholar 

  69. G. Weiss and D. Schoenfeld, Tetrahedron,22, 2511 (1966).

    Google Scholar 

  70. T. Nozoe and I. Murata, Aromatic Compounds, London (1973), p. 201.

  71. A. T. Soldatenkov, M. W. Baghdadi, V. O. Fedorov, and N. S. Prostakov, Khim. Geterotsikl. Soedin., No. 9, 1212 (1986).

  72. A. N. Nesmeyanov, N. A. Ustynyuk, N. S. Prostakov, A. T. Soldatenkov, V. G. Pleshkov, K. Urga, Yu. A. Ustynyuk, O. I. Trifnova, and Yu. F. Orgipenko, J. Organometall. Chem.,231, 5 (1982).

    Google Scholar 

  73. G. M. Bogdanov and Yu. G. Bundel', Khim. Geterotsikl. Soedin., No. 9, 1155 (1983).

  74. C. B. Reese, J. Am. Chem. Soc.,84, 3979 (1962).

    Google Scholar 

  75. A. G. Anderson and H. L. Ammon, Tetrahedron Lett.,23, 3601 (1967).

    Google Scholar 

  76. G. Bergson and A. M. Weidler, Acta Chem. Scand.,16, 2464 (1962).

    Google Scholar 

  77. J. J. Eisch and F. J. Gadek, J. Org. Chem.,36, 3376 (1971).

    Google Scholar 

  78. R. Borsdorf, W. Schroth, and G. Fischer, Z. Chem.,4, 68 (1964).

    Google Scholar 

  79. H.-J. Timpe and A. A. Shoraji, Z. Chem.,21, 448 (1981)

    Google Scholar 

  80. J. Beger and W. Treibs, Ann.,652, 204 (1962).

    Google Scholar 

  81. R. A. Abramovitch and J. G. Saha, Adv. Heterocycl. Chem.,6, 229 (1966).

    Google Scholar 

  82. R. A. Abramovitch and C.-S. Giam, Canad. J. Chem.,40, 213 (1962).

    Google Scholar 

  83. N. S. Prostakov, A. T. Soldatenkov, V. O. Fedorov, A. I. Semikopnyi, I. A. Sytinskii, M. M. Borisov, and E. P. Mufazalova, Khim.-Farm. Zh., No. 8, 67 (1981).

  84. I. W. Elliot, J. Heterocycl. Chem.,3, 361 (1966).

    Google Scholar 

  85. A. P. Gray, E. E. Spinner, and C. J. Carralito, J. Am. Chem. Soc.,76, 2792 (1954).

    Google Scholar 

  86. É. S. Lavrinovich, P. P. Zarin'sh, L. P. Osis, I. A. Rubenis, and Yu. É Fridmanis, Advances in Heterocyclic Chemistry [in Russian], Vol. 1, Zinatne, Riga (1979), p. 125.

    Google Scholar 

  87. G.-I. Timpe, E. M. Klokova, and A. V. El'tsov, Zh. Org. Khim.,14, 673 (1978).

    Google Scholar 

  88. N. S. Prostakov, A. T. Soldatenkov, and M. W. Baghdadi, Khim. Geterotsikl. Soedin., No. 5, 705 (1982).

  89. J. Braun and J. Nelles, Ber.,70, 1767 (1937).

    Google Scholar 

  90. A. T. Soldatenkov, M. W. Baghdadi, A. A. Fomichev, and N. S. Prostakov, Zh. Org. Khim.,18, 902 (1982).

    Google Scholar 

  91. A. T. Soldatenkov, M. W. Baghdadi, P. K. Radjan, O. S. Brindkha, S. L. Edogiaveria, A. A. Fomichen, and N. S. Prostakov, Zh. Org. Khim.,19, 1326 (1983).

    Google Scholar 

  92. S. A. Soldatova, J. A. Rodriguez Alarcon, and A. T. Soldatenkov, Khim. Geterotsikl. Soedin., No. 1, 79 (1994).

Download references

Author information

Authors and Affiliations

Authors

Additional information

Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 1, pp. 3–20, January, 1995.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Soldatenkov, A.T., Prostakov, N.S. & Obynochnyi, A.A. Cyclopenta- and indenopyridine anhydrobases. A review. Chem Heterocycl Compd 31, 1–16 (1995). https://doi.org/10.1007/BF01171281

Download citation

  • Received:

  • Issue Date:

  • DOI: https://doi.org/10.1007/BF01171281

Keywords

Navigation