Advertisement

Chemistry of Heterocyclic Compounds

, Volume 35, Issue 1, pp 3–22 | Cite as

Preparation and reactions of isoflavone heteroanalogs (a review)

  • M. S. Frasinyuk
  • V. P. Khilya
Article

Abstract

Methods for preparation of 3-hetarylchromones, which are isoflavone heteroanalogs, and the reactions of these compounds with either preservation or opening of the pyrone ring are reviewed.

Keywords

Organic Chemistry Isoflavone Pyrone Pyrone Ring 
These keywords were added by machine and not by the authors. This process is experimental and the keywords may be updated as the learning algorithm improves.

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

References

  1. 1.
    A. Nohara, T. Imetani, and Y. Sanno, Ger. Offen 2317899; Chem. Abstr.,80, 14932 (1974).Google Scholar
  2. 2.
    A. Nohara, Tetrahedron Lett., No. 13, 1187 (1974).Google Scholar
  3. 3.
    A. Nohara, T. Ishiguro, H. Kuriki, T. Saijo, H. Sigihara, M. Kanno, and Y. Sanno, J. Med. Chem.,20, 141 (1977).Google Scholar
  4. 4.
    A. Nohara, T. Ishiguro, and Y. Sanno, Ger. Offen 2614836; Chem. Abstr.,86, 72661 (1977).Google Scholar
  5. 5.
    M. Strandmann, M. P. Cohen, S. Klutchko, and J. Shavel, Pat. Specif. Au. 516897 Aust.; Chem. Abstr.,100, 34549 (1984).Google Scholar
  6. 6.
    M. Strandmann, M. P. Cohen, S. Klutchko, and J. Shavel, U.S. Patent 4116971; Chem. Abstr.,90, 72203 (1979).Google Scholar
  7. 7.
    T. Kato, A. Nohara, T. Kawarazaki, and Y. Sawa, Takeda Kenkyusho Ho,37, No. 3-4, 195 (1978); Chem. Abstr.,90, 152093 (1979).Google Scholar
  8. 8.
    Co. Kito, H. Kuriki, S. Chiba, and K. Kikuchi, Takeda Kenkyusho Ho,37, No. 3-4, 202 (1978); Chem. Abstr.,90, 197584 (1979).Google Scholar
  9. 9.
    Co. Kito, H. Kuriki, and K. Kikuchi, Takeda Kenkyusho Ho,37, No. 3-4, 228 (1978); Chem. Abstr.,90, 197586 (1979).Google Scholar
  10. 10.
    A. Nohara, H. Kuriki, T. Ishiguro, T. Saijo, K. Ukawa, Y. Maki, and Y. Sanno, J. Med. Chem.,22, 290 (1979).Google Scholar
  11. 11.
    A. Nohara, T. Ishiguro, and K. Ukawa, Japan Kokai Tokkyo Koho 79059279; Chem. Abstr.,91, 175358 (1979).Google Scholar
  12. 12.
    Y. Kanai, Y. Nakai, N. Nakajima, and S. Tanayama, Xenobiotica,9, 33 (1979); Chem. Abstr.,91, 101757 (1979).Google Scholar
  13. 13.
    P. Cozzi, N. Mongelli, A. Pillan, M. Bergamaschi, and P. Lovisolo, French Patent 2477545; Chem. Abstr.,96, 122508 (1982).Google Scholar
  14. 14.
    P. Cozzi, A. Pillan, and P. Lovisolo, Belgian Patent 893917, Chem. Abstr.,99, 5629 (1983).Google Scholar
  15. 15.
    P. Cozzi, U. Branzoli, P. Lovisolo, G. Orsini, G. Garganico, A. Pillan, and A. Chiari, J. Med. Chem.,29, 404 (1986).Google Scholar
  16. 16.
    V. P. Khilya, A. L. Kazakov, G. M. Golubushina, V. N. Mel'nik, and T. M. Tkachuk, Khim.-Farm Zh.,15, 40 (1981).Google Scholar
  17. 17.
    V. P. Khilya, L. G. Grishko, T. I. Zhirova, I. A. Gorchakova, I. P. Kupchevskaya, and G. M. Golubushina, Khim.-Farm. Zh.,14, 24 (1980).Google Scholar
  18. 18.
    V. P. Khilya, I. P. Kupchevska, A. I. Salikhova, L. G. Grishko, and F. S. Babichev, Khim. Geterotsikl. Soedin., No. 9, 1180 (1977).Google Scholar
  19. 19.
    C. P. Garg, S. V. Prabha, and R. P. Kapoor, Indian. J. Chem., Sect. B,24B, 1197 (1985).Google Scholar
  20. 20.
    V. P. Khilya, V. Szabo, L. G. Grishko, D. V. Vikhman, F. S. Babichev, and V. A. Dymovich, Khim. Geterotsikl. Soedin., No. 8, 1030 (1975).Google Scholar
  21. 21.
    V. P. Khilya, L. G. Grishko, and D. V. Vikhman, Khim.-Farm. Zh.,10, 74 (1976).Google Scholar
  22. 22.
    M. K. Rastogi, R. P. Kapoor, and C. P. Garg, Indian J. Chem., Sect. B,16B, 245 (1978).Google Scholar
  23. 23.
    M. K. Rastogi, C. Kamla, R. P. Kapoor, and C. P. Garg, Indian J. Chem., Sect. B,17B, 34 (1979).Google Scholar
  24. 24.
    R. P. Kapoor, M. K. Rastogi, R. Khanna, and C. P. Garg, Indian J. Chem., Sect. B,23B, 390 (1984).Google Scholar
  25. 25.
    R. P. Kapoor, V. P. Sharma, Om V. Singh, and C. P. Garg, Indian J. Chem., Sect. B,30B, 1152 (1991).Google Scholar
  26. 26.
    S. Gronowitz and R. Ekman, Arkiv Kemi,17, No. 9, 93 (1960); Chem. Abstr.,55, 27294 (1961).Google Scholar
  27. 27.
    I. P. Kupchevskaya and V. P. Khilya, Dokl. Akad. Nauk UkrSSR, No. 6, 66 (1981).Google Scholar
  28. 28.
    I. P. Kupchevskaya and V. P. Khilya, Dokl. Akad. Nauk UkrSSR, No. 7, 46 (1981).Google Scholar
  29. 29.
    V. Szabo, L. G. Grishko, S. Borbely, and V. P. Khilya, Khim. Geterotsikl. Soedin., No. 2, 174 (1975).Google Scholar
  30. 30.
    V. P. Khilya, L. G. Grishko, and V. Szabo, Khim. Geterotsikl. Soedin., No. 10, 1317 (1972).Google Scholar
  31. 31.
    V. P. Khilya, L. G. Grishko, N. V. Sukharenko, and V. Szabo, Zh. Org. Khim.,8, 1085 (1972).Google Scholar
  32. 32.
    V. P. Khilya, L. G. Grishko, L. I. Shevchenko, L. I. Barvinok, V. A. Dymovich, and V. Szabo, Khim. Geterotsikl. Soedin., No. 9, 1202 (1973).Google Scholar
  33. 33.
    V. G. Pivovarenko and V. P. Khilya, Khim. Geterotsikl. Soedin., No. 5, 595 (1992).Google Scholar
  34. 34.
    V. Szabo, S. Borbely, L. G. Grishko (Grisko), and V. P. Khilya (Chilia), Magy. Kem. Foly,82, 263 (1976).Google Scholar
  35. 35.
    V. G. Pivovarenko and V. P. Khilya, Khim. Geterotsikl. Soedin., No. 5, 625 (1991).Google Scholar
  36. 36.
    V. G. Pivovarenko and V. P. Khilya, Dokl. Akad. Nauk UkrSSR, No. 7, 44 (1985).Google Scholar
  37. 37.
    M. Yu. Kornilov, V. P. Khilya, and L. G. Grishko, Zh. Org. Khim.,9, 2568 (1973).Google Scholar
  38. 38.
    A. Kish, V. Szabo, L. G. Grishko, and V. P. Khilya, Dokl. Akad. Nauk UkrSSR, No. 3, 232 (1977).Google Scholar
  39. 39.
    V. P. Khilya, L. G. Grishko, and T. N. Sokolova, Khim. Geterotsikl. Soedin., No. 12, 1593 (1975).Google Scholar
  40. 40.
    N. V. Gorbulenko, N. N. Shimko, and V. P. Khilya, Dokl. Akad. Nauk UkrSSR, Ser. B, No. 5, 117 (1991).Google Scholar
  41. 41.
    N. B. Gorbulenko, M. S. Frasinyuk, and V. P. Khilya, Khim. Geterotsikl. Soedin., No. 4, 464 (1994).Google Scholar
  42. 42.
    N. V. Gorbulenko, O. V. Gaiduk, A. S. Ogorodniichuk, V. P. Khilya, and V. V. Shilin, Dokl. Akad. Nauk UkrSSR, Ser. B, No. 9, 144 (1991).Google Scholar
  43. 43.
    M. S. Frasinyuk, N. V. Gorbulenko, and V. P. Khilya, Khim. Geterotsikl. Soedin., No. 9, 1237 (1997).Google Scholar
  44. 44.
    M. S. Frasinyuk and V. P. Khilya, Khim. Geterotsikl. Soedin., No. 10, 1377 (1997).Google Scholar
  45. 45.
    V. P. Khilya, L. G. Grishko, and T. I. Zhul', Khim. Geterotsikl. Soedin., No. 8, 1108 (1976).Google Scholar
  46. 46.
    V. P. Khilya, L. G. Grishko, T. M. Sokolova, and V. Szabo, Zh. Org. Khim.,9, 2572 (1973).Google Scholar
  47. 47.
    N. V. Gorbulenko, V. P. Khilya, M. V. Kolotusha, and L. I. Shevchenko, Dokl. Akad. Nauk UkrSSR, Ser. B, No. 11, 34 (1990).Google Scholar
  48. 48.
    N. V. Gorbulenko, S. A. Kirpa, and V. P. Khilya, Khim. Geterotsikl. Soedin., No. 1, 29 (1993).Google Scholar
  49. 49.
    N. V. Gorbulenko, V. P. Khilya, and S. A. Kirpa, Dokl. Akad. Nauk UkrSSR, Ser. B, No. 12, 22 (1990).Google Scholar
  50. 50.
    V. P. Khilya, I. G. Belashova, and G. M. Golubushina, Dokl. Akad. Nauk UkrSSR, No. 3, 257 (1978).Google Scholar
  51. 51.
    A. L. Kazakov, V. P. Khilya, V. V. Mezheritskii, and G. Litkei, Natural and Modified Isoflavonoids [in Russian], Izd. Rostovsk. Univ., Rostov-on-the-Don (1985).Google Scholar
  52. 52.
    V. P. Khilya, V. F. Vakulenko, and I. P. Kupchevskaya, Khim. Geterotsikl. Soedin., No. 1, 25 (1979).Google Scholar
  53. 53.
    V. P. Khilya, M. Yu. Kornilov, I. P. Kupchevskaya, and V. F. Vakulenko, Ukr. Khim. Zh.,44, 265 (1978).Google Scholar
  54. 54.
    V. P. Khilya, N. A. Yasnikova, A. L. Kazakov, and G. M. Golubushina, Ukr. Khim. Zh.,48, 765 (1982).Google Scholar
  55. 55.
    V. P. Khilya, N. A. Yasnikova, A. L. Kazakov, and G. M. Golubushina, Dokl. Akad. Nauk UkrSSR, Ser. B, No. 5, 60 (1981).Google Scholar
  56. 56.
    V. P. Khilya, T. M. Tkachuk, I. P. Kupchevskaya, and G. M. Golubushina, Dokl. Akad. Nauk UkrSSR, No. 5, 61 (1980).Google Scholar
  57. 57.
    V. P. Khilya, V. Szabo, L. G. Grishko, D. V. Vikhman, and F. S. Babichev, Zh. Org. Khim.,9, 2561 (1973).Google Scholar
  58. 58.
    L. G. Grishko, M. Yu. Kornilov, and V. P. Khilya, Zh. Org. Khim.,10, 1277 (1974).Google Scholar
  59. 59.
    V. Szabo, V. P. Khilya (Chilja), L. G. Grishko (Grisko), F. S. Babichev, and J. Borda, Magy. Kem. Foly,83, No. 6, 274 (1977).Google Scholar
  60. 60.
    V. G. Pivovarenko, V. P. Khilya, V. N. Kovalev, and S. A. Vasil'ev, Khim. Prirodn. Soedin., No. 4, 511 (1988).Google Scholar
  61. 61.
    N. V. Gorbulenko, A. V. Turov, and V. P. Khilya, Khim. Geterotsikl. Soedin., No. 4, 505 (1995).Google Scholar
  62. 62.
    V. P. Khilya, V. G. Pivovarenko, and F. S. Babichev, Ukr. Khim. Zh.,52, 187 (1986).Google Scholar
  63. 63.
    N. V. Gorbulenko, G. M. Golubushina, I. P. Kupchevskaya, and V. P. Khilya, Dokl. Akad. Nauk UkrSSR, No. 7, 623 (1978).Google Scholar
  64. 64.
    I. P. Kupchevskaya and V. P. Khilya, Dokl. Akad. Nauk UkrSSR, No. 2, 119 (1979).Google Scholar
  65. 65.
    V. P. Khilya, F. S. Babichev, V. G. Pivovarenko, A. S. Ogorodniichuk, A. P. Koval', and S. I. Tyukhtenko, Ukr. Khim. Zh.,53, 404 (1987).Google Scholar
  66. 66.
    W. William and L. Benzce, Belgian Patent 633436; Chem. Abstr.,61, 1840 (1964).Google Scholar
  67. 67.
    D. Connor, P. Young, and M. Strandtmann, J. Heterocycl. Chem.,14, 143 (1977).Google Scholar
  68. 68.
    V. A. Litenko, Yu. M. Volovenko, and F. S. Babichev, Ukr. Khim. Zh.,49, 1202 (1983).Google Scholar
  69. 69.
    Yu. M. Volovenko, F. S. Babichev, and V. A. Litenko, USSR Patent 883040; Chem. Abstr.,96, 181148 (1982).Google Scholar
  70. 70.
    P. Cozzi and A. Pillan, J. Heterocycl. Chem.,23, 1693 (1986).Google Scholar
  71. 71.
    P. Cozzi, N. Mongelli, and A. Pillan, J. Heterocycl. Chem.,21, 311 (1984).Google Scholar
  72. 72.
    P. Cozzi and A. Pillan, J. Heterocycl. Chem.,22, 441 (1985).Google Scholar
  73. 73.
    P. Cozzi, G. Garganico, A. Pillan, and U. Branzoli, Ger. Offen 3324069; Chem. Abstr.,100, 174829 (1984).Google Scholar
  74. 74.
    J. H. Parsons, R. G. Hunt, S. E. Leach, E. Susan, A. Percival, A. D. Buss, D. E. Green, and M. Mellor, Eur. Pat. Appl. 247760; Chem. Abstr.,108, 131827 (1978).Google Scholar
  75. 75.
    A. Nohara, T. Ishiguro, K. Ukawa, T. Kato, and Y. Sawa, Japan Kokai 78018575; Chem. Abstr.,89, 43430 (1978).Google Scholar
  76. 76.
    A. Nohara, T. Ishiguro, K. Ukawa, T. Kato, and Y. Sawa, Japan Kokai 78018573; Chem. Abstr.,89, 6328 (1978).Google Scholar
  77. 77.
    A. Nohara, T. Ishiguro, K. Ukawa, T. Kato, and Y. Sawa, Japan Kokai 78018574; Chem. Abstr.,89, 24320 (1978).Google Scholar
  78. 78.
    A. Nohara, T. Ishiguro, K. Ukawa, T. Kato, and Y. Sawa, Japan Kokai 78018572; Chem. Abstr.,89, 43431 (1978).Google Scholar
  79. 79.
    T. Kato, A. Nohara, T. Kawarazaki, and Y. Sawa, Japan Kokai Tokkyo Koho 78116376; Chem. Abstr.,90, 103963 (1979).Google Scholar
  80. 80.
    I. Ilima, M. Miyazaki, and T. Tanaka, Japan Kokai 76026877; Chem. Abstr.,85, 159884 (1976).Google Scholar
  81. 81.
    L. Grishko, A. Turov, V. Khilya, G. Litkei, and T. Patonay, Acta Chim. Hung.,112, 401 (1983).Google Scholar
  82. 82.
    L. G. Grishko, A. V. Turov, I. A. Potrusaeva, and V. P. Khilya, Ukr. Khim. Zh.,49, 174 (1983).Google Scholar
  83. 83.
    L. G. Grishko, A. V. Turov, M. G. Spasenov, and V. P. Khilya, Khim. Geterotsikl. Soedin., No. 9, 1202 (1981).Google Scholar
  84. 84.
    C. W. Winter and C. S. Hamilton, J. Am. Chem. Soc.,74, 3999 (1952).Google Scholar
  85. 85.
    J. Colonge and A. Guyot, Bull. Soc. Chim. France, No. 3, 329 (1958).Google Scholar
  86. 86.
    E. K. Orlova, N. S. Tolmacheva, L. N. Meshcheryakova, and V. A. Zagorevskii, Khim.-Farm. Zh.,7, 14 (1973).Google Scholar
  87. 87.
    R. P. Kapoor, M. K. Rastogi, and C. P. Garg, Indian J. Chem., Sect. B,23B, 285 (1984).Google Scholar
  88. 88.
    C. P. Garg, V. P. Sharma, V. Chhabra, and R. P. Kapoor, Indian J. Chem., Sect. B,27B, 469 (1988).Google Scholar
  89. 89.
    P. D. Clarke, A. O. Fitton, M. Kosmirak, H. Suschitzky, and J. L. Suschitzky, J. Chem. Soc., Perkin Trans. I, No. 8, 1747 (1985).Google Scholar
  90. 90.
    A. O. Fitton, M. Kosmirak, H. Suschitzky, and J. L. Suschitzky, Tetrahedron Lett.,23, 3953 (1982).Google Scholar
  91. 91.
    K. Gorlitzer and K. Michels, Arch. Pharm.,321, 567 (1988).Google Scholar
  92. 92.
    C. K. Ghosh, A. K. Mitra, and A. Parta, J. Indian Chem. Soc.,57, 450 (1980).Google Scholar
  93. 93.
    C. K. Ghosh and D. K. Sinha Roy, Indian J. Chem., Sect. B,16B, 727 (1978).Google Scholar
  94. 94.
    G. Rihs, I. Sigg, G. Haas, and T. Winkler, Helv. Chim. Acta,68, 1935 (1985).Google Scholar
  95. 95.
    C. K. Ghosh, C. Pal, J. Maiti, and M. Sarkar, J. Chem. Soc., Perkin Trans. I, No. 6, 1489 (1988).Google Scholar
  96. 96.
    C. K. Ghosh, C. Pal, J. Maiti, and M. Sarkar, Indian. J. Chem., Sect. B,28B, 448 (1989).Google Scholar
  97. 97.
    G. Litkei, T. Patonay, and E. Peli, J. Org. Proc. Int.,19, 44 (1987); Chem. Abstr.,106, 175982 (1987).Google Scholar
  98. 98.
    M. Shanker, R. B. Reddy, G. Mouli, and Y. D. Reddy, Asian J. Chem.,4, 166 (1992); Chem. Abstr.,116, 128767 (1992).Google Scholar
  99. 99.
    A. Levai, Pharmazie,36, 449 (1981).Google Scholar
  100. 100.
    A. Nohara, ASC Symp. Ser. (1978, Publ. 1980), Vol. 118 (Drugs Affecting Respiration Synthesis), p. 125; Chem. Abstr.,93, 373 (1980).Google Scholar
  101. 101.
    G. Litkei, T. Patonay, E. Peli, and V. P. Khilya, Pharmazie,44, 791 (1989).Google Scholar
  102. 102.
    A. K. Baruah, D. Prajapati, and J. S. Sandhu, J. Chem. Soc., Perkin Trans. I, No. 9, 1995 (1987).Google Scholar
  103. 103.
    A. K. Baruah, D. Prajapati, and J. S. Sandhu, Heterocycles,27, 1127 (1988).Google Scholar
  104. 104.
    A. K. Baruah, D. Prajapati, and J. S. Sandhu, Tetrahedron,44, 1241 (1988).Google Scholar
  105. 105.
    C. K. Ghosh, A. Bhattacharyya, G.-D. Pratim, Indian J. Chem., Sect. B,26B, 423 (1987).Google Scholar
  106. 106.
    V. P. Khilya, L. G. Grishko, and F. S. Babichev, Khim. Geterotsikl. Soedin., No. 11, 1474 (1976).Google Scholar
  107. 107.
    L. G. Grishko, V. P. Khilya, M. F. Sedyuko, and D. Litkei, Ukr. Khim. Zh.,51, 211 (1985).Google Scholar
  108. 108.
    V. P. Khilya, L. G. Grishko, and T. L. Davidkova, Khim. Geterotsikl. Soedin., No. 7, 892 (1980).Google Scholar
  109. 109.
    V. P. Khilya, I. P. Kupchevskaya, A. L. Kazakov, T. M. Tkachuk, and G. M. Golubushina, Khim. Geterotsikl. Soedin., No. 3, 321 (1982).Google Scholar
  110. 110.
    V. P. Khilya, N. V. Gorbulenko, and V. V. Trachevskii, Dokl. Akad. Nauk UkrSSR, Ser. B, No. 1, 123 (1991).Google Scholar
  111. 111.
    V. P. Khilya, G. M. Golubushina, E. N. Meita, and M. Yu. Kornilov, Dokl. Akad. Nauk UkrSSR, No. 4, 57 (1980).Google Scholar
  112. 112.
    V. P. Khilya, M. Yu. Kornilov, N. V. Gorbulenko, G. M. Golubushina, E. N. Kovtun, N. V. Kolotusha, and G. V. Panasenko, Khim. Geterotsikl. Soedin., No. 11, 1542 (1985).Google Scholar
  113. 113.
    M. S. Frasinyuk, A. V. Turov, and V. P. Khilya, Khim. Geterotsikl. Soedin., No. 8, 1072 (1998).Google Scholar
  114. 114.
    V. P. Khilya, L. G. Grishko, and V. Szabo, Khim. Geterotsikl. Soedin., No. 10, 1321 (1972).Google Scholar
  115. 115.
    M. V. Artemenko, V. A. Litenko, E. G. Lampeka, V. P. Khilya, N. V. Gorbulenko, and D. A. Stakhkov, Dokl. Akad. Nauk UkrSSR, Ser. B, No. 12, 31 (1988).Google Scholar

Copyright information

© Kluwer Academic/Plenum 1999

Authors and Affiliations

  • M. S. Frasinyuk
  • V. P. Khilya

There are no affiliations available

Personalised recommendations