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New method for the synthesis of potentially biologically active isoindolinium and dihydroisoindolinium salts and their condensed analogs (review)

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Chemistry of Heterocyclic Compounds Aims and scope

Abstract

The base-catalyzed intramolecular cyclization of the diene-synthesis type of quaternary ammonium salts, which leads to potentially biologically active isoindolinium and dihydroisoindolinium salts and their condensed analogs, is examined. The alkaline cleavage of the products, a possible reaction mechanism, and the results of biological tests are discussed.

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References

  1. G. Briger and J. N. Bennet, Chem. Rev., 80, 63 (1980).

    Google Scholar 

  2. A. Fallis, Canad. J. Chem., 62, 183 (1984).

    Google Scholar 

  3. I. Iwai and I. Ide, Chem. Farm. Bull., 97, 1094 (1964).

    Google Scholar 

  4. A. I. Bartlett, T. Laird, and W. D. Ollis, J. Chem. Soc., Chem. Commun., No. 13, 496 (1974).

    Google Scholar 

  5. A. I. Bartlett, T. Laird, and W. D. Ollis, J. Chem. Soc., Perkin Trans., 1315 (1975).

  6. R. W. Jamison, T. Laird, and W. D. Ollis, J. Chem. Soc., Chem. Commun., No. 9, 556 (1972).

    Google Scholar 

  7. P. Garrat, J. Am. Chem. Soc., 98, 3255 (1975).

    Google Scholar 

  8. A. T. Babayan, K. Ts. Tagmazyan, and É. S. Ananyan, Dokl. Akad. Nauk Armyansk. SSR, 38, 157 (1964).

    Google Scholar 

  9. A. T. Babayan, K. Ts. Tagmazyan, and É. S. Ananyan, Izv. Akad. Nauk Armyansk. SSR, Khim. Nauka, 18, 252 (1965).

    Google Scholar 

  10. A. T. Babayan, K. Ts. Tagmazyan, and É. S. Ananyan, Izv. Akad. Nauk Armyansk. SSR, Khim. Nauka, 18, 262 (1965).

    Google Scholar 

  11. A. T. Babayan, K. Ts. Tagmazyan, and G. T. Babayan, Armyansk. Khim. Zh., 19, 678 (1966).

    Google Scholar 

  12. A. T. Babayan, K. Ts. Tagmazyan, G. T. Babayan, and A. G. Oganesyan, Zh. Org. Khim., 4, 1323 (1968).

    Google Scholar 

  13. A. T. Babayan, K. Ts. Tagmazyan, and G. T. Babayan, Armyansk. Khim. Zh., 19, 685 (1966).

    Google Scholar 

  14. A. T. Babayan, K. Ts. Tagmazyan, and L. P. Karapetyan, Dokl. Akad. Nauk Armyansk. SSR, 15, 51 (1975).

    Google Scholar 

  15. A. T. Babayan, K. Ts. Tagmazyan, and L. P. Karapetyan, Dokl. Akad. Nauk Armyansk. SSR, 16, 40 (1975).

    Google Scholar 

  16. A. T. Babayan, É. O. Chukhadzhyan, G. T. Babayan, and I. A. Abramyan, Dokl. Akad. Nauk Armyansk. SSR, 48, 54 (1969).

    Google Scholar 

  17. A. T. Babayan, É. O. Chukhadzhyan, G. T. Babayan, and I. A. Abramyan, USSR Author's Certificate No. 281,474; Byull. Izobret., No. 29, 40 (1970).

  18. A. T. Babayan, É. O. Chukhadzhyan, and G. T. Babayan, Zh. Org. Khim., 6, 1161 (1970).

    Google Scholar 

  19. I. Iwai and T. Hiraoka, Chem. Farm. Bull., No. 11(12), 1556 (1963).

    Google Scholar 

  20. A. T. Babayan, É. O. Chukhadzhyan, G. T. Babayan, Él. O. Chukhadzhyan, and F. S. Kinonyan, Armyansk. Khim. Zh., 23, 149 (1970).

    Google Scholar 

  21. Él. O. Chukhadzhyan, É. O. Chukhadzhyan, and A. T. Babayan, Zh. Org. Khim., 10, 46 (1974).

    Google Scholar 

  22. A. T. Babayan, É. O. Chukhadzhyan, and L. A. Manasyan, Armyansk. Khim. Zh., 31, 489 (1978).

    Google Scholar 

  23. É. O. Chukhadzhyan, G. L. Gabrielyan, and A. T. Babayan, Zh. Org. Khim., 11, 325 (1975).

    Google Scholar 

  24. T. Laird and W. D. Ollis, J. Chem. Soc., No. 9, 557 (1972).

    Google Scholar 

  25. T. Laird, W. D. Ollis, and J. O. Sutherland, J. Chem. Soc., Perkin I, No. 4, 1477 (1980).

    Google Scholar 

  26. I. Iwai and T. Hiraoka, Chem. Farm. Bull., No. 11(12), 1564 (1964).

    Google Scholar 

  27. É. O. Chukhadzhyan and A. T. Babayan, Armyansk. Khim. Zh., 24, 1066 (1971).

    Google Scholar 

  28. É. O. Chukhadzhyan, G. L. Gabrielyan, and A. T. Babayan, Armyansk. Khim. Zh., 29, 71 (1976).

    Google Scholar 

  29. A. T. Babayan, É. O. Chukhadzhyan, and L. A. Manasyan, Zh. Org. Khim., 15, 942 (1979).

    Google Scholar 

  30. A. T. Babayan, É. O. Chukhadzhyan, V. P. Akopyan, and L. A. Manasyan, USSR Author's Certificate No. 104,714 (1981).

  31. A. T. Babayan, S. T. Kocharyan, P. S. Chobanyan, and T. A. Azizyan, Dokl. Akad. Nauk Armyansk. SSR, 51, 227 (1970).

    Google Scholar 

  32. A. T. Babayan, S. T. Kocharyan, Dzh. V. Grigoryan, and P. S. Chobanyan, Zh. Org. Khim., 7, 2253 (1971).

    Google Scholar 

  33. A. T. Babayan, S. T. Kocharyan, Dzh. V. Grigoryan, T. L. Razina, and V. S. Voskanyan, Armyansk. Khim. Zh., 29, 213 (1974).

    Google Scholar 

  34. A. T. Babayan, É. O. Chukhadzhyan, and Él. O. Chukhadzhyan, Dokl. Akad. Nauk Armyansk. SSR, 52, 281 (1971).

    Google Scholar 

  35. A. T. Babayan, É. O. Chukhadzhyan, and Él. O. Chukhadzhyan, Zh. Org. Khim., 9, 467 (1973).

    Google Scholar 

  36. A. T. Babayan, É. O. Chukhadzhyan, and É. O. Chukhadzhyan, USSR Author's Certificate No. 382,623; Byull. Izobret., No. 23, 62 (1973).

  37. A. T. Babayan, É. O. Chukhadzhyan, Él. O. Chukhadzhyan, and G. L. Gabrielyan, Armyansk. Khim. Zh., 29, 173 (1976).

    Google Scholar 

  38. É. O. Chukhadzhyan, Él. O. Chukhadzhyan, K. G. Shakhatuni, and A. T. Babayan, Khim. Geterotsikl. Soedin., No. 5, 615 (1989).

    Google Scholar 

  39. A. T. Babayan, V. P. Akopyan, É. O. Chukhadzhyan, and K. G. Shakhatuni, USSR Author's Certificate No. 849,744 (1980).

  40. A. T. Babayan, É. O. Chukhadzhyan, A. S. Saratikov, Él. O. Chukhadzhyan, K. G. Shakhatuni, N. S. Livshits, and L. V. Simak, USSR Author's Certificate No. 961,310 (1981).

  41. É. O. Chukhadzhyan, K. G. Shakhatuni, Él. O. Chukhadzhyan, and A. T. Babayan, Khim. Geterotsikl. Soedin., No. 6, 759 (1991).

    Google Scholar 

  42. É. O. Chukhadzhyan, K. G. Shakhatuni, Él. O. Chukhadzhyan, and A. T. Babayan, Armyansk. Khim. Zh., 49, 241 (1991).

    Google Scholar 

  43. É. O. Chukhadzhyan, Doctoral Dissertation, Institute of Organic Chemistry, Academy of Sciences of the USSR, Yerevan (1985).

    Google Scholar 

  44. A. T. Babayan, É. O. Chukhadzhyan, and Él. O. Chukhadzhyan, USSR Author's Certificate No. 1,519,178 (1988).

  45. É. O. Chukhadzhyan, G. L. Gabrielyan, and A. T. Babayan, Zh. Org. Khim., 14, 2502 (1978).

    Google Scholar 

  46. C. Engelbert, J. Org. Chem., 45, 1497 (1980).

    Google Scholar 

  47. Ya. D. Samuilov, R. L. Nurillina, and A. I. Konovalov, Zh. Org. Khim., 18, 2253 (1982).

    Google Scholar 

  48. A. T. Babayan, É. O. Chukhadzhyan, K. G. Shakhatuni, S. V. Lindeman, and Yu. T. Struchkov, Armyansk. Khim. Zh., 38, 44 (1985).

    Google Scholar 

  49. A. T. Babayan, É. O. Chukhadzhyan, Él. O. Chukhadzhyan, G. L. Gabrielyan, V. G. Andrianov, A. A. Karapetyan, and Yu. T. Struchkov, Armyansk. Khim. Zh., 32, 881 (1979).

    Google Scholar 

  50. A. T. Babayan, É. O. Chukhadzhyan, and Él. O. Chukhadzhyan, Zh. Org. Khim., 7, 470 (1971).

    Google Scholar 

  51. A. T. Babayan, É. O. Chukhadzhyan, Él. O. Chukhadzhyan, and R. P. Babayan, Zh. Org. Khim., 13, 518 (1977).

    Google Scholar 

  52. A. V. Atomyan, É. O. Chukhadzhyan, and A. T. Babayan, Armyansk. Khim. Zh., 37, 664 (1984).

    Google Scholar 

  53. É. O. Chukhadzhyan, L. A. Manasyan, and A. T. Babayan, Khim. Geterotsikl. Soedin., No. 11, 1481 (1988).

    Google Scholar 

  54. A. T. Babayan, É. O. Chukhadzhyan, Él. O. Chukhadzhyan, and R. P. Babayan, Zh. Org. Khim., 10, 1638 (1974).

    Google Scholar 

  55. É. 0. Chukhadzhyan, Él. O. Chukhadzhyan, L. A. Manasyan, and A. T. Babayan, Armyansk. Khim. Zh., 34, 46 (1981).

    Google Scholar 

  56. A. T. Babayan and I. A. Abramyan, Dokl. Akad. Nauk Armyansk. SSR, 50, 144 (1970).

    Google Scholar 

  57. I. A. Abramyan-Babayan and A. T. Babayan, Armyansk. Khim. Zh., 25, 19 (1972).

    Google Scholar 

  58. I. A. Abramyan-Babayan, A. V. Atomyan, and A. T. Babayan, Armyansk. Khim. Zh., 25, 30 (1972).

    Google Scholar 

  59. A. T. Babayan, A. V. Atomyan, I. S. Kislina, and M. I. Vinnik, Armyansk. Khim. Zh., 28, 958 (1975).

    Google Scholar 

  60. I. A. Abramyan-Babayan, A. V. Atomyan, and A. T. Babayan, Dokl. Akad. Nauk Armyansk. SSR, 57, 81 (1973).

    Google Scholar 

  61. A. V. Atomyan, N. P. Churkina, A. T. Babayan, I. S. Kislina, and M. I. Vinnik, Armyansk. Khim. Zh., 34, 389 (1981).

    Google Scholar 

  62. A. V. Atomyan, N. P. Churkina, A. T. Babayan, I. S. Kislina, and M. I. Vinnik, Izv. Akad. Nauk SSSR, Ser. Khim., No. 3, 525 (1981).

    Google Scholar 

  63. A. V. Atomyan, É. O. Chukhadzhyan, and A. T. Babayan, Armyansk. Khim. Zh., 36, 639 (1983).

    Google Scholar 

  64. T. L. Jacobs and S. Singer, J. Org. Chem., 17, 475 (1952).

    Google Scholar 

  65. W. J. Gensler and J. Casella, J. Am. Chem. Soc., 80, 1376 (1958).

    Google Scholar 

  66. F. Ya. Perveev, Zh. Obshch. Khim., 18, 686 (1948).

    Google Scholar 

  67. M. Bertrand, Comptes Rend., 244, 1790 (1957).

    Google Scholar 

  68. L. I. Smith and J. S. Swenson, J. Am. Chem. Soc., 79, 2962 (1957).

    Google Scholar 

  69. G. Eglinton, E. R. H. Johns, G. M. Mansfield, and M. C. Whiting, J. Chem. Soc., No. 9, 3197 (1954).

    Google Scholar 

  70. R. A. Raphael, Acetylenic Compounds in Organic Synthesis, London (1955), p. 136.

  71. G. D. Appleyard and C. J. M. Stirling, J. Chem. Soc. (C), No. 5, 1904 (1969).

    Google Scholar 

  72. A. T. Babayan, K. Ts. Tagmazyan, and G. O. Torosyan, Zh. Org. Khim., 9, 1156 (1973).

    Google Scholar 

  73. A. T. Babayan, K. Ts. Tagmazyan, and G. O. Torosyan, Armyansk. Khim. Zh., 27, 485 (1974).

    Google Scholar 

  74. A. T. Babayan, K. Ts. Tagmazyan, and R. S. Mkrtchyan, Zh. Org. Khim., 10, 1642 (1974).

    Google Scholar 

  75. A. T. Babayan, R. A. Aleksanyan, and É. O. Chukhadzhyan, USSR Author's Certificate No. 718,445; Byull. Izobret., No. 8, 98 (1980).

  76. A. T. Babayan, R. A. Aleksanyan, and É. O. Chukhadzhyan, USSR Author's Certificate No. 767,096; Byull. Izobret., No. 36, 117 (1980).

  77. A. T. Babayan, É. O. Chukhadzhyan, and Él. O. Chukhadzhyan, USSR Author's Certificate No. 718,444; Byull. Izobret., No. 8, 98 (1980).

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  1. Institute of Organic Chemistry, Academy of Sciences of Armenia, 375094, Yerevan

    É. O. Chukhadzhyan

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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 4, pp. 435–449, April, 1993.

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Chukhadzhyan, É.O. New method for the synthesis of potentially biologically active isoindolinium and dihydroisoindolinium salts and their condensed analogs (review). Chem Heterocycl Compd 29, 363–376 (1993). https://doi.org/10.1007/BF00529871

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