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Chemistry of Heterocyclic Compounds

, Volume 36, Issue 12, pp 1361–1401 | Cite as

Phosphorus-containing Derivatives of Indole and Pyrrole. (Review)

  • P. A. Gurevich
  • V. A. Yaroshevskaya
Article

Abstract

Data on the synthesis and chemical properties of the phosphorus-containing derivatives of indoles and pyrroles, published in 1976-1998, are reviewed. The introduction of substituents containing tri- and tetracoordinated phosphorus atom into the heterocycle and the side chain is discussed. Information on the biological activity is presented.

indole pyrrole phosphorylation 

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REFERENCES

  1. 1.
    R. J. Sundberg, The Chemistry of Indoles, Academic Press, New York, London (1970), p. 489.Google Scholar
  2. 2.
    W. J. Houlihan, Indoles, Wiley-Interscience, Part 1 (1972), p. 587; Part 2 (1972), p. 615; Part 3 (1979), p. 586.Google Scholar
  3. 3.
    G. I. Zhungietu, V. A. Budylin, and A. N. Kost, Preparative Chemistry of Indole [in Russian], Shtiintsa, Kishinev (1975), p. 262.Google Scholar
  4. 4.
    G. I. Zhungietu and M. A. Rekhter, Isatin and its Derivatives [in Russian], Shtiintsa, Kishinev (1977), p. 288.Google Scholar
  5. 5.
    A. Hofmann, R. Heim, and A. Brack, Helv. Chim. Acta, 42, 1557 (1959).Google Scholar
  6. 6.
    D. L. J. Hughes, Org. Prep. Proc. Int., 25, 609 (1993).Google Scholar
  7. 7.
    O. Mingoia, Gazz. Chim. Ital., 60, 144 (1930).Google Scholar
  8. 8.
    D. Redmore, Chem. Rev., 71, 315 (1971).Google Scholar
  9. 9.
    A. I. Razumov, P. A. Gurevich, and S. Yu. Baigil'dina, Khim. Geterotsikl. Soedin., 867 (1976).Google Scholar
  10. 10.
    P. A. Gurevich, V. V. Moskva, and V. V. Kiselev, Advances of Science and Technology. Organic Chemistry [in Russian], VINITI, Moscow, 30, 3 (1993).Google Scholar
  11. 11.
    T. V. Komina, Thesis for Candidate of Chemical Sciences [in Russian], Kazan (1982).Google Scholar
  12. 12.
    P. A. Gurevich, A. I. Razumov, T. V. Komina, G. Yu. Klimentova, and T. V. Zykova, Zh. Obshch. Khim., 55, 1257 (1985).Google Scholar
  13. 13.
    V. V. Moskva, P. A. Gurevitch, T. V. Komina, and A. I. Rasumov, Conf. Internat. de Chimie du Phosphore. Resumes, Nice, France (1983), Abstr. 71.Google Scholar
  14. 14.
    P. A. Gurevich, V. V. Moskva, T. V. Komina, P. A. Stepanov, V. V. Kiselev, and V. I. Molostov, Advances in the Chemistry of Nitrogen Heterocycles [in Russian], Izd. Rost. Un-ta, Rostov-on-Don (1982), p. 229.Google Scholar
  15. 15.
    A. I. Razumov, P. A. Gurevich, V. V. Moskva, T. V. Komina, V. V. Kiselev, P. A. Stepanov, and G. Yu. Klimentova, Abstracts of the Seventh All-Union Conference on the Chemistry of Organophosphorus Compounds [in Russian], Leningrad (1982), p. 239.Google Scholar
  16. 16.
    A. I. Razumov, P. A. Gurevich, S. Yu. Baigil'dina, T. V. Zykova, and R. A. Salakhutdinov, Zh. Obshch. Khim., 44, 2587 (1974).Google Scholar
  17. 17.
    S. Yu. Baigil'dina, Thesis for Candidate of Chemical Sciences [in Russian], Kazan (1975).Google Scholar
  18. 18.
    G. Z. Akhmetova, P. A. Gurevich, V. V. Moskva, and V. P. Arkhipov, Zh. Obshch. Khim., 69, 160 (1999).Google Scholar
  19. 19.
    Z. R. Musabekova, Thesis for Candidate of Chemical Sciences [in Russian], Kazan (1994).Google Scholar
  20. 20.
    A. M. Kibardin, P. I. Gryaznov, T. Kh. Gazizov, and A. N. Pudovik, Izv. Akad. Nauk SSSR. Ser. Khim., 1826 (1987).Google Scholar
  21. 21.
    P. A. Gurevich, V. V. Kiselev, V. V. Moskva, S. F. Maksyutova, and T. V. Zykova, Zh. Obshch. Khim., 53, 238 (1983).Google Scholar
  22. 22.
    P. A. Gurevich, V. V. Kiselev, V. V. Moskva, T. V. Zykova, and S. F. Maksyutova, Zh. Obshch. Khim., 53, 696 (1983).Google Scholar
  23. 23.
    P. A. Gurevich, V. V. Kiselev, V. V. Moskva, T. V. Zykova, and R. A. Salakhutdinov, Zh. Obshch. Khim., 53, 2145 (1983).Google Scholar
  24. 24.
    I. Lafaille, F. Mathis, and R. Burgada, Compt. Rend. Acad. Sci., 270C, 1138 (1970).Google Scholar
  25. 25.
    Z. R. Musabekova, P. A. Gurevich, I. A. Aleksandrova, and T. Kh. Gazizov, Zh. Obshch. Khim., 62, 708 (1992).Google Scholar
  26. 26.
    D. Purdela and R. Vylchanu, Chemistry of Organophosphorus Compounds [in Russian], Nauka, Moscow (1972), p. 752.Google Scholar
  27. 27.
    S. B. Khrebtova, L. K. Vasyanina, A. A. Nasarov, M. P. Koroteev, and E. E. Nifant'ev, XI International Conference on the Chemistry of Phosphorus Compounds [in Russian], Kazan (1996), p. 113.Google Scholar
  28. 28.
    A. A. Tolmachev, S. P. Ivonin, A. V. Kharchenko, and E. S. Kozlov, Zh. Obshch. Khim., 60, 1668 (1990).Google Scholar
  29. 29.
    B. Bogdan, Phosphorus and Sulfur, 113, 209 (1996).Google Scholar
  30. 30.
    A. A. Tolmachev, S. P. Ivonin, A. A. Chaikovskaya, T. E. Terekovskaya, S. I. Dovgopoly, and A. N. Kostjuk, XI International Conference on the Chemistry of Phosphorus Compounds [in Russian], Kazan (1996), p. 87.Google Scholar
  31. 31.
    A. A. Tolmachev, A. V. Kharchenko, and A. D. Mitrokhin, St. Petersburg Meetings, IX International Symposium on the Chemistry of Phosphorus [in Russian], St. Petersburg (1993), p. 96.Google Scholar
  32. 32.
    A. A. Tolmachev, S. P. Ivonin, A. A. Yurchenko, and E. V. Zarudnitskii, St. Petersburg Meetings 98. Chemistry and Application of Organophosphorus, Organosulfur, and Organosilicon Compounds [in Russian], St. Petersburg (1998), p. 32.Google Scholar
  33. 33.
    P. A. Stepanov, P. A. Gurevich, A. I. Razumov, and T. V. Zykova, Zh. Obshch. Khim., 61, 86 (1991).Google Scholar
  34. 34.
    P. A. Gurevich, A. I. Razumov, and P. A. Stepanov, Zh. Obshch. Khim., 52, 1928 (1982).Google Scholar
  35. 35.
    P. A. Stepanov, Thesis for Candidate of Chemical Sciences [in Russian], Kazan (1983).Google Scholar
  36. 36.
    A. P. Terent'ev, G. Van-Lun', and M. N. Preobrazhenskaya, Zh. Obshch. Khim., 32, 1335 (1962).Google Scholar
  37. 37.
    M. N. Preobrazhenskaya, M. F. Fedotova, N. P. Sorokina, O. B. Ogareva, N. V. Uvarova, and N. N. Suvorov, Zh. Obshch. Khim., 34, 1310 (1964).Google Scholar
  38. 38.
    P. A. Gurevich, P. A. Stepanov, T.V. Zykova, and A. I. Razumov, Zh. Obshch. Khim., 53, 2395 (1983).Google Scholar
  39. 39.
    G. L. Matevosyan, S. N. Vodovatova, and P. M. Zavlin, Zh. Obshch. Khim., 50, 2803 (1980).Google Scholar
  40. 40.
    P. A. Gurevich, A. I. Razumov, T. V. Komina, G. Yu. Klimentova, and T. V. Zykova, Zh. Obshch. Khim., 55, 1327 (1985).Google Scholar
  41. 41.
    P. A. Gurevich, T. V. Komina, G. Yu. Klimentova, T. V. Zykova, and G. I. Ruzal', Khim.-Farm. Zh., 833 (1984).Google Scholar
  42. 42.
    M. B. Gazizov and R. A. Khairullin, Advances of Science and Technology. Organic Chemistry [in Russian], VINITI, Moscow, 15, 1 (1990).Google Scholar
  43. 43.
    A. I. Razumov, P. A. Gurevich, S. Kh. Nurtdinov, S. A. Muslimov, and L. M. Tyl'nova, Zh. Obshch. Khim., 47, 1421 (1977).Google Scholar
  44. 44.
    P. A. Gurevich, Thesis for Doctor of Chemical Sciences [in Russian], Moscow (1985).Google Scholar
  45. 45.
    G. Z. Akhmetova, P. A. Gurevich, V. V. Moskva, and V. P. Arkhipov, Zh. Obshch. Khim., 68, 2057 (1998).Google Scholar
  46. 46.
    A. A. Tolmachev, S. O. Ivonin, and A. A. Yurchenko, Phosphorus and Sulfur, 113, 209 (1996).Google Scholar
  47. 47.
    A. I. Razumov, P. A. Gurevich, and S. A. Muslimov, Zh. Obshch. Khim., 46, 2749 (1976).Google Scholar
  48. 48.
    A. I. Razumov, P. A. Gurevich, S. A. Muslimov, T. V. Komina, T. V. Zykova, and R. A. Salakhutdinov, Zh. Obshch. Khim., 50, 778 (1980).Google Scholar
  49. 49.
    S. A. Muslimov, Thesis for Candidate of Chemical Sciences [in Russian], Kazan (1978).Google Scholar
  50. 50.
    E. S. Batyeva, V. A. Al'fonsov, G. U. Zamaletdinova, and A. N. Pudovik, Zh. Obshch. Khim., 46, 2204 (1976).Google Scholar
  51. 51.
    B. E. Ivanov and S. V. Samurina, Izv. Akad. Nauk SSSR. Ser. Khim., 2075 (1974).Google Scholar
  52. 52.
    A. I. Razumov, P. A. Gurevich, and S. A. Muslimov, USSR Inventor's Certificate 614111; Byull. Izobr., No. 25 (1978).Google Scholar
  53. 53.
    A. I. Razumov, P. A. Gurevich, V. V. Moskva, B. I. Buzykin, T. V. Komina, G. Yu. Klimentova, and P. A. Stepanov, V All-Union Colloquium “Chemistry, Biochemistry, and Pharmacology of Indole Derivatives” [in Russian], Izd. Tbilisskogo Un-ta, Tbilisi (1981), p. 34.Google Scholar
  54. 54.
    P. A. Gurevich, A. I. Razumov, T. V. Komina, G. Yu. Klimentova, and S. Yu. Baigil'dina, XII Mendeleev Congress on General and Applied Chemistry [in Russian], Nauka, Moscow, No. 4, 214 (1981).Google Scholar
  55. 55.
    G. F. Smith, Adv. Heterocycl. Chem., 2, 287 (1963).Google Scholar
  56. 56.
    W. E. Noland and C. F. Hammer, J. Org. Chem., 25, 1525 (1960).Google Scholar
  57. 57.
    O. Schmitz, Ber., 63, 323 (1930).Google Scholar
  58. 58.
    J. I. G. Cadogan, D. J. Sears, and D. M. Smith, J. Chem. Soc. C, 1314 (1969).Google Scholar
  59. 59.
    F. Troxler, F. Seemann, and A. Hofmann, Helv. Chim. Acta, 42, 2073 (1959).Google Scholar
  60. 60.
    L. M. Morozovskaya, M. A. Kolesnikova, and N. N. Suvorov, Zh. Obshch. Khim., 38, 2788 (1968).Google Scholar
  61. 61.
    H. Timmler, Ger. Offen 2030508; Chem. Abstr., 76, 85920 (1972).Google Scholar
  62. 62.
    G. Z. Akhmetova, P. A. Gurevich, V. V. Moskva, and V. P. Arkhipov, Zh. Obshch. Khim., 68, 2055 (1998).Google Scholar
  63. 63.
    E. F. Janson and E. K. Fields, J. Org. Chem., 27, 402 (1962).Google Scholar
  64. 64.
    E. A. Torralba and T. C. Myers, J. Org. Chem., 22, 972 (1957).Google Scholar
  65. 65.
    N. F. Albertson, US Patent 2980692; Chem. Abstr., 56, 457 (1962).Google Scholar
  66. 66.
    J. Szmuszkoviez, J. Am. Chem. Soc., 80, 3782 (1958).Google Scholar
  67. 67.
    H. Hellman and O. Schumacher, Ann., 640, 79 (1961).Google Scholar
  68. 68.
    J. A. Enkhoorn, S. Silva, D. Osmund, and V. Snieckus, Can. J. Chem., 5, 792 (1973).Google Scholar
  69. 69.
    A. Chakh and K. Kel'ner, Chemistry and Application of Organophosphorus Compounds [in Russian], Nauka, Moscow (1974), p. 184.Google Scholar
  70. 70.
    P. I. Yagodinets, I. N. Chernyuk, E. M. Volynskaya, I. I. Shevchuk, and V. N. Kushnir, Zh. Obshch. Khim., 54, 772, (1984).Google Scholar
  71. 71.
    D. Magarathnam and P. C. Srinivasan, Synthesis, 926 (1982).Google Scholar
  72. 72.
    H. Fischer and G. Ort, Chemistry of Pyrrole [Russian translation], ONTI, Leningrad (1937), p. 122.Google Scholar
  73. 73.
    A. Arcoria, S. Fisichella, E. Maccarone, and G. Scarlata, J. Heterocycl. Chem., 12, 215 (1975).Google Scholar
  74. 74.
    D. Kh. Yarmukhametova, B. V. Kudryavtsev, and L. I. Anpilova, Izv. Akad. Nauk SSSR. Ser. Khim., 435 (1974).Google Scholar
  75. 75.
    I. A. Tovannidis, Phosphorus and Sulfur, 12, 249 (1982).Google Scholar
  76. 76.
    G. I. Zhungietu, F. N. Chukhrai, and A. I. Tolmachev, Zh. Vses. Khim. Obshch. D. I. Mendeleeva, 15, 590 (1970).Google Scholar
  77. 77.
    G. Z. Akhmetova, V. V. Moskva, P. A. Gurevich, and V. P. Arkhipov, Zh. Obshch. Khim., 67, 1212 (1997).Google Scholar
  78. 78.
    A. Mustafa, M. M. Sidky, and F. M. Soliman, Tetrahedron, 22, 393 (1966).Google Scholar
  79. 79.
    Kh. I. Riisalu, V. V. Vasil'ev, and B. I. Ionin, Zh. Obshch. Khim., 54, 563 (1984).Google Scholar
  80. 80.
    M. R. H. Mahran, M. D. Khidre, and W. M. Abdou, Phosphorus, Sulfur, Silicon, Relat. Elem., 101, 17 (1995).Google Scholar
  81. 81.
    E. E. Nifant'ev, T. S. Kukareva, and O. V. Davydochkina, IV Conference “Bioantioxidant” [in Russian], Moscow, 1, 207 (1993).Google Scholar
  82. 82.
    P. A. Gurevich, G. Z. Akhmetova, A. T. Gubaidullin, V. V. Moskva, and I. A. Litvinov, Zh. Obshch. Khim., 68, 1570 (1998).Google Scholar
  83. 83.
    G. Z. Akhmetova, Thesis for Candidate of Chemical Sciences [in Russian], Kazan (1998).Google Scholar
  84. 84.
    A. N. Pudovik and I. V. Gur'yanova, Chemistry and Application of Organophosphorus Compounds. Proceedings of IV Conference [in Russian], Nauka, Moscow (1972), p. 164.Google Scholar
  85. 85.
    A. I. Razumov, P. A. Gurevich, and S. Yu. Baigil'dina, Zh. Obshch. Khim., 44, 2586 (1974).Google Scholar
  86. 86.
    A. I. Razumov, P. A. Gurevich, and S. Yu. Baigil'dina, USSR Inventor's Certificate 422740; Byull. Izobr., No. 13 (1974).Google Scholar
  87. 87.
    Yu. E. Utkin, A. S. Sergeeva, V. N. Tarasov, V. K. Promonenkov, and S. V. Ivin, Zh. Obshch. Khim., 37, 2710 (1967).Google Scholar
  88. 88.
    P. A. Gurevich, V. V. Kiselev, V. V. Moskva, and G. I. Ruzal', Khim.-Farm. Zh., 51 (1983).Google Scholar
  89. 89.
    G. E. Lathourakis and K. E. Litinas, J. Chem. Soc. Perkin Trans. 1, 491 (1996).Google Scholar
  90. 90.
    G. Z. Akhmetova, P. A. Gurevich, V. V. Moskva, N. V. Kokhan, and V. P. Arkhipov, Zh. Obshch. Khim., 67, 877 (1997).Google Scholar
  91. 91.
    A. N. Pudovik, I. V. Gur'yanova, and E. A. Ishmaeva, Reactions and methods of Investigation of Organic Compounds [in Russian], Khimiya, Moscow, 19, 59 (1968).Google Scholar
  92. 92.
    E. E. Nifant'ev, Chemistry of Hydrophosphoryl Compounds [in Russian], Nauka, Moscow (1983), p. 78.Google Scholar
  93. 93.
    H. Gross, L. Brennecke, and B. Costisella, J. Prakt. Chem., 318, 277 (1976).Google Scholar
  94. 94.
    B. A. Arbuzov, E. N. Dianova, A. V. Fuzhenkova, and A. F. Lisin, Izv. Akad. Nauk SSSR. Ser. Khim., 1825 (1975).Google Scholar
  95. 95.
    S. V. Fridland, L. B. Kashevarova, and L. V. Ryapisova, XI International Conference on Chemistry of Phosphorus Compounds [in Russian], Kazan (1996), p. 139.Google Scholar
  96. 96.
    L. V. Ryapisova, L. B. Kashevarova, I. G. Shaikhiev, and S. V. Fridland, Zh. Obshch. Khim., 67, 2061 (1997).Google Scholar
  97. 97.
    E. N. Koz'minykh, E. S. Berezina, and V. O. Koz'minykh, Zh. Obshch. Khim., 66, 1128 (1996).Google Scholar
  98. 98.
    A. A. Sobanov, A. V. Zolotukhin, and V. I. Galkin, Abstracts of Conference in Memory of I. M. Shermergorn [in Russian], Kazan (1996), p. 46.Google Scholar
  99. 99.
    A. I. Razumov, P. A. Gurevich, and S. Yu. Baigil'dina, USSR Inventor's Certificate 437771; Byull. Izobr., No. 28 (1974).Google Scholar
  100. 100.
    A. I. Razumov, P. A. Gurevich, S. Yu. Baigil'dina, and M. V. Alparova, Zh. Obshch. Khim., 44, 2585 (1974).Google Scholar
  101. 101.
    A. I. Razumov, P. A. Gurevich, R. I. Tarasova, and S. Yu. Bail'gildina, Zh. Obshch. Khim., 46, 33 (1976).Google Scholar
  102. 102.
    N. V. Kolotilo, P. P. Onysko, and A. A. Sinitsa, Zh. Obshch. Khim., 65, 1221 (1995).Google Scholar
  103. 103.
    A. I. Razumov, P. A. Gurevich, G. I. Ruzal', S. Yu. Baigil'dina, and S. A. Muslimov, Kazan; Dep. TsNIINTI, No. DR-169 (1980).Google Scholar
  104. 104.
    E. A. Muzafarova, G. Z. Akhmetova, P. A. Gurevich, and V. V. Moskva, Zh. Obshch. Khim., 66, 523 (1996).Google Scholar
  105. 105.
    P. A. Gurevich, V. V. Moskva, G. Z. Akhmetova, and E. Muzafarova, All-Russian Conference Chemistry of Organophosphorus Compounds and Prospects for their Development at the Threshold of the XXI Century [in Russian], Moscow (1998), p. 47.Google Scholar
  106. 106.
    P. A. Gurevich, V. V. Moskva, G. Yu. Klimentova, V. V. Kiselev, Kazan; Dep. NIITEKHIM, No. 207-khp-87 (1987).Google Scholar
  107. 107.
    P. A. Gurevich, V. V. Kiselev, V. V. Moskva, and N. A. Moskva, Zh. Obshch. Khim., 54, 471 (1984).Google Scholar
  108. 108.
    P. A. Gurevich, G. Yu. Klimentova, V. V. Moskva, T. V. Zykova, F. Sh. Shagvaleev, and V. V. Kiselev, Zh. Obshch. Khim., 57, 2316 (1987).Google Scholar
  109. 109.
    B. S. Drach and E. P. Sviridov, Zh. Obshch. Khim., 43, 1648 (1973).Google Scholar
  110. 110.
    P. A. Gurevich, V. V. Moskva, V. V. Kiselev, and G. Yu. Klimentova, VIII All-Union Conference on the Chemistry of Organophosphorus Compounds, dedicated to the 80th Anniversary of the Arbuzov Reaction [in Russian], Kazan (1985), p. 9.Google Scholar
  111. 111.
    M. R. Gratchev, G. I. Kurochkina, V. V. Negrebetsky, Phosphorus, Sulfur, Silicon, Relat. Elem., 88, 257 (1994).Google Scholar
  112. 112.
    Q. Mingoia, Gazz. Chim. Ital., 62, 333 (1932).Google Scholar
  113. 113.
    A. I. Razumov, P. A. Gurevich, and S. Yu. Baigil'dina, USSR Inventor's Certificate 458558; Byull. Izobr., No. 4 (1975).Google Scholar
  114. 114.
    B. A. Khaskin, Reactions and Methods of Investigation of Organic Compounds [in Russian], Khimiya, Moscow, 20, 129 (1969).Google Scholar
  115. 115.
    G. I. Ruzal', A. I. Razumov, P. A. Gurevich, and S. A. Muslimov, Aspects of Epidemiology and Applied Immunology [in Russian], Leningrad, 3, 24 (1977).Google Scholar
  116. 116.
    P. A. Gurevich, A. I. Razumov, S. A. Muslimov, T. V. Komina, S. Yu. Baigil'dina, T. V. Zykova, and R. A. Salakhutdinov, Advances in the Chemistry of Nitrogen-Containing Heterocycles [in Russian], Zinatne, Riga, 2, 28 (1979).Google Scholar
  117. 117.
    V. G. Rozinov, G. A. Pensionerova, L. V. Izhboldina, V. I. Donskikh, V. E. Kolbina, A. I. Mikhaleva, and K. E. Korostova, VII All-Union Conference on the Chemistry of Organophosphorus Compounds [in Russian], Kazan (1982), p. 147.Google Scholar
  118. 118.
    V. G. Rozinov, G. A. Pensionerova, V. I. Donskikh, L. M. Sergienko, O. V. Petrova, A. V. Kalabina, and A. I. Mikhaleva, Zh. Obshch. Khim., 54, 2241 (1984).Google Scholar
  119. 119.
    G. A. Pensionerova, V. G. Rozinov, A. V. Kalabina, V. I. Donskikh, G. V. Ratovskii, and M. Yu. Dmitrichenko, Zh. Obshch. Khim., 52, 2491 (1982).Google Scholar
  120. 120.
    L. N. Harris, Tetrahedron Lett., 4465 (1966).Google Scholar
  121. 121.
    V. G. Rozinov, L. V. Izhboldina, G. A. Pensionerova, L. M. Sergeenko, V. I. Donskikh, S. F. Malysheva, N. G. Glukhikh, and G. V. Ratovskii, Zh. Obshch. Khim., 54, 1051 (1984).Google Scholar
  122. 122.
    R. S. Greenley, M. L. Nielsen, and L. Parts, J. Org. Chem., 29, 1009 (1964).Google Scholar
  123. 123.
    J. J. Pappas, and E. Gancher, J. Heterocycl. Chem., 86, 265 (1969).Google Scholar
  124. 124.
    S. Hunig and H. Steinmetzer, Tetrahedron Lett., 643 (1972).Google Scholar
  125. 125.
    H. Tolkmith, E. C. Britton, and C. F. Holoway, US Patent 2802823; Chem. Abstr., 52, 2065 (1958).Google Scholar
  126. 126.
    H. Tolkmith, E. C. Britton, and C. F. Holoway, US Patent 2802824; Chem. Abstr., 52, 2083 (1958).Google Scholar
  127. 127.
    S. R. Wilson and M. F. Price, Synth. Commun., 12, 657 (1982).Google Scholar
  128. 128.
    T. Koizumi, V. Kobayashi, H. Amitani, and A. Voshii, J. Org. Chem., 42, 3459 (1977).Google Scholar
  129. 129.
    A. F. Grapov, L. V. Razvodskaya, and N. N. Mel'nikov, Chemistry and Application of Organophosphorus Compounds. Proceedings of V All-Union Conference [in Russian], Nauka, Moscow (1974), p. 254.Google Scholar
  130. 130.
    H. Pohlemann, H. Schroeder, H. Stummeyer, and H. Adolphi, US Patent 2865912; Chem. Abstr., 53, 11420 (1959).Google Scholar
  131. 131.
    N. P. Grechkin and L. N. Grishina, Zh. Obshch. Khim., 48, 2203 (1978).Google Scholar
  132. 132.
    N. P. Grechkin and L. N. Grishina, Zh. Obshch. Khim., 52, 1113 (1982).Google Scholar
  133. 133.
    L. N. Grishina, G. A. Kashafutdinov, and N. P. Grechkin, Zh. Obshch. Khim., 48, 558 (1978).Google Scholar
  134. 134.
    M. C. J. Hewson and R. Schmutzler, Phosphorus and Sulfur, No. 8, 9 (1980).Google Scholar
  135. 135.
    R. Schmutzler, Angew. Chem., 76, 893 (1964).Google Scholar
  136. 136.
    A. F. Grapov, L. V. Razvodskaya, and N. N. Mel'nikov, Zh. Obshch. Khim., 44, 281 (1974).Google Scholar
  137. 137.
    K. Issleib and K. P. Dopfe, Z. Chem., 22, 215 (1982).Google Scholar
  138. 138.
    B. Marianne, J. Xian-Yun, and W. Halina, Synthesis, 1074 (1995).Google Scholar
  139. 139.
    N.P. Chizhov and F. S. Noskov, Abstracts of Conference of the Military Medical Academy [in Russian], Leningrad (1972), p. 116.Google Scholar
  140. 140.
    A. N. Grinev, Khim.-Farm. Zh., No. 5, 6 (1970).Google Scholar
  141. 141.
    N. V. Khromov-Borisov, L. S. Efros, and A. B. Tomchin, Zh. Obshch. Khim., 44, 1641 (1974).Google Scholar
  142. 142.
    P. A. Gurevich, A. I. Razumov, S. A. Muslimov, T. V. Komina, and R. L. Yafarova, Kazan, Dep TsNIINTI, No. DR-170 (1980).Google Scholar
  143. 143.
    A. I. Razumov, P. A. Gurevich, and L. A. Monakhova, USSR Inventor's Certificate 362025; Byull. Izobr., No. 2, (1973).Google Scholar
  144. 144.
    I. V. Zakonnikova, A. V. Val'dman, M. M. Kozlovskaya, and G. F. Rzhevskaya, Farmakologiya i Toksikologiya, No. 4, 6 (1980).Google Scholar
  145. 145.
    A. I. Razumov, P. A. Gurevich, S. A. Muslimov, and V. G. Usacheva, Zh. Obshch. Khim., 46, 2381 (1976).Google Scholar
  146. 146.
    A. I. Razumov, D. Kh. Yarmukhametova, P. A. Gurevich, B. V. Kudryavtsev, and S. A. Muslimov, Zh. Obshch. Khim., 48, 228 (1978).Google Scholar
  147. 147.
    P. A. Gurevich, A. I. Razumov, S. A. Muslimov, and G. Yu. Klimentova, Kazan, Dep. NIITEKHIM, No. 687-khp-D82 (1982).Google Scholar
  148. 148.
    A. N. Pudovik and G. E. Yastrebova, Usp. Khim., 39, 1190 (1970).Google Scholar
  149. 149.
    A. N. Pudovik, A. M. Shakirova, and V. I. Nikitina, Dokl. Akad. Nauk, 182, 1338 (1968).Google Scholar
  150. 150.
    S. F. Chen, S. D. Kumar, and M. Tishler, Tetrahedron Lett., 49, 5461 (1983).Google Scholar
  151. 151.
    P. A. Gurevich, S. Yu. Baigil'dina, L. F. Mal'tseva, and G. I. Ruzal', Kazan, Dep. NIITEKHIM, No. 49khp-85Dep. (1985).Google Scholar
  152. 152.
    P. A. Gurevich, T. V. Komina, and G. Yu. Klimentova, Zh. Obshch. Khim., 54, 2199 (1984).Google Scholar
  153. 153.
    M. N. Preobrazhenskaya, K. B. Kholodkovskaya, E. G. Balashova, and N. N. Suvorov, Khim. Geterotsikl. Soedin., Zinatne, Riga, Collection 1, 28 (1967).Google Scholar
  154. 154.
    A. I. Razumov, P. A. Gurevich, B. V. Kudryavtsev, and S. Yu. Baigil'dina, Zh. Obshch. Khim., 47, 2538 (1977).Google Scholar
  155. 155.
    I. L. Vladimirova, A. F. Grapov, and V. I. Lomakina, Reactions and Methods of Investigation of Organic Compounds [in Russian], Khimiya, Moscow, 16, 24 (1966).Google Scholar
  156. 156.
    L. I. Volovel'skii, S. Yu. Baigil'dina, P. A. Gurevich, and N. V. Popova, USSR Inventor's Certificate 488813; Byull. Izobr., No. 39 (1975).Google Scholar
  157. 157.
    P. M. Zavlin, Chemistry and Application of Organophosphorus Compounds. Proceedings of IV Conference [in Russian], Nauka, Moscow (1972), p. 134.Google Scholar
  158. 158.
    N. N. Suvorov and V. S. Shashkov, Chemistry and Pharmacology of Agents for Treatment of Radiation Sickness [in Russian], Atomizdat, Moscow (1975), p. 39.Google Scholar
  159. 159.
    P. A. Gurevich, A. I. Razumov, and P. A. Stepanov, Zh. Obshch. Khim., 53, 941 (1983).Google Scholar
  160. 160.
    K. V. Vatsuro and G. L. Mishchenko, Named Reactions in Organic Chemistry [in Russian], Khimiya, Moscow (1976), p. 528.Google Scholar
  161. 161.
    M. Somei, T. Hasegawa, and S. Kaneco, Heterocycles, 10, 1983 (1983).Google Scholar
  162. 162.
    V. I. Shvedov, E. K. Panisheva, T. F. Vlasova, and A. N. Grinev, Khim. Geterotsikl. Soedin., 1354 (1973).Google Scholar
  163. 163.
    S. A. Monti and W. O. Johnson, Tetrahedron, 26, 3685 (1970).Google Scholar
  164. 164.
    A. K. Sheinkman, Khim. Geterotsikl. Soedin., 3 (1974).Google Scholar
  165. 165.
    A. K. Sheinkman, G. V. Samoilenko, S. N. Baranov, and P. A. Gurevich, USSR Inventor's Certificate 407900; Byull. Izobr., No. 47 (1973).Google Scholar
  166. 166.
    G. V. Samoilenko and P. A. Gurevich, Symposium II on the Chemistry and Technology of Heterocyclic Compounds from Mineral Fuels [in Russian], Donetsk (1973), p. 10.Google Scholar
  167. 167.
    A. K. Sheinkman, G. V. Samoilenko, S. N. Baranov, P. A. Gurevich, and A. N. Prilepskaya, IV All-Union Colloquium Chemistry and Pharmacology of Indole Compounds [in Russian], Shtiintsa, Kishinev (1975), p. 71.Google Scholar
  168. 168.
    A. K. Sheinkman, G. V. Samoilenko, and S. N. Baranov, Chemistry and Application of Organophosphorus Compounds [in Russian], Nauka, Moscow (1974), p. 366.Google Scholar
  169. 169.
    R. T. Brown, J. A. Jouli, and P. G. Samms, General Organic Chemistry, Vol. 8, Khimiya, Moscow (1985), p. 488.Google Scholar
  170. 170.
    N. N. Suvorov, V. P. Mamaev, and V. M. Rodionov, Reactions and Methods of Investigation of Organic Compounds [in Russian], Khimiya, Moscow, 9, 21 (1959).Google Scholar
  171. 171.
    I. I. Grandberg and V. I. Sorokin, Usp. Khim., 43, 266 (1974).Google Scholar
  172. 172.
    A. E. Arbuzov and V. M. Tikhvinskii, in: A. E. Arbuzov, Selected Works on the Chemistry of Organophosphorus Compounds [in Russian], Nauka, Moscow (1976).Google Scholar
  173. 173.
    M. J. Gallagher and F. G. Mann, J. Chem. Soc., 4855 (1963).Google Scholar
  174. 174.
    K. C. Srivastava and K. D. Berlin, J. Org. Chem., 37, 4487 (1972).Google Scholar
  175. 175.
    K. Issleib, R. Wolff, and M. Lengies, J. Prakt. Chem., 318, 207 (1976).Google Scholar
  176. 176.
    A. I. Razumov, B. G. Liorber, V. V. Moskva, and M. P. Sokolov, Usp. Khim., 1199 (1973).Google Scholar
  177. 177.
    A. I. Razumov and P. A. Gurevich, USSR Inventor's Certificate 172796; Byull. Izobr., No. 14 (1965).Google Scholar
  178. 178.
    A. I. Razumov and P. A. Gurevich, Zh. Obshch. Khim., 37, 1615 (1967).Google Scholar
  179. 179.
    A. I. Razumov and P. A. Gurevich, Trudy Kazanskogo Khim.-Tekhnol. In-ta, 36, 480 (1967).Google Scholar
  180. 180.
    E. Fischer and T. Schmidt, Ber., 21, 1811 (1888).Google Scholar
  181. 181.
    V. A. Budylin, A. N. Kost, and E. D. Matveeva, Khim. Geterotsikl. Soedin., 55 (1972).Google Scholar
  182. 182.
    B. Miller and E. R. Matjeka, J. Am. Chem. Soc., 102, 4772 (1980).Google Scholar
  183. 183.
    J. Xian-Yun, X. Fa-Gao, C. Wan-Yi, and Hu Bing-Fang, Chin. J. Org. Chem., 59, 622 (1994).Google Scholar
  184. 184.
    A. Coutere, E. Deniau, Y. Gimbert, and P. Graddaudon, Tetrahedron, 49, 1431 (1993).Google Scholar
  185. 185.
    P. A. Gurevich, A. I. Razumov, R. L. Yafarova, T. V. Komina, and F. Kh. Kutumova, Zh. Obshch. Khim., 51, 1671 (1981).Google Scholar
  186. 186.
    P. A. Gurevich, Kazan, Dep. NIITEKHIM, No. 54-khp-85Dep. (1985).Google Scholar
  187. 187.
    Yu. P. Kitaev and B. I. Buzykin, Hydrazones [in Russian], Nauka, Moscow (1974), p. 257.Google Scholar
  188. 188.
    C. Y. Yuan, C. Z. Li, and G. H. Wang, Phosphorus, Sulfur, Silicon, Relat. Elem., 75, 147 (1993).Google Scholar
  189. 189.
    P. A. Gurevich, P. A. Stepanov, and A. I. Razumov, Zh. Obshch. Khim., 53, 2394 (1983).Google Scholar
  190. 190.
    E. N. Dolzhnikova, E. N. Tsvetkov, G. S. Petrova, R. V. Poponova, and B. V. Zhdanov, Zh. Obshch. Khim., 48, 525 (1978).Google Scholar
  191. 191.
    H. N. Rydon and S. Siddappa, J. Chem. Soc., 2462 (1951).Google Scholar
  192. 192.
    M. R. Tirakyan, G. A. Panosyan, and Yu. M. Dagnyan, Zh. Obshch. Khim., 62, 2684 (1992).Google Scholar
  193. 193.
    A. A. Tolmachev, Thesis for Candidate of Chemical Sciences [in Russian], Kiev (1986).Google Scholar
  194. 194.
    N. A. Polezhaeva, P. G. Sakhibullina, T. G. Kostyunina, A. V. Prosvirkin, N. I. Tiryshkin, and G. A. Chmutova, Zh. Obshch. Khim., 66, 1134 (1996).Google Scholar
  195. 195.
    A. V. Prosvirkin, N. A. Polezhaeva, G. A. Chmutova, and V. G. Sakhibullina, Chemistry and Application of Organophosphorus, Organosulfur, and Organosilicon Compounds. St. Petersburg Meetings 98, St. Petersburg (1998), p. 276.Google Scholar
  196. 196.
    B. A. Trofimov and A. I. Mikhaleva, N-Vinylpyrroles [in Russian], Nauka, Novosibirsk (1984), p. 262.Google Scholar
  197. 197.
    L. N. Yakhontov and R. G. Glushkov, Synthetic Medicinal Substances [in Russian], Meditsina, Moscow (1983), p. 272.Google Scholar
  198. 198.
    T. V. Moskovkina, Zh. Org. Khim., 33, 138 (1997).Google Scholar
  199. 199.
    M. N. Preobrazhenskaya, Usp. Khim., 36, 1760 (1967).Google Scholar
  200. 200.
    T. V. Golovko, N. P. Solov'eva, and V. G. Granik, Mendeleev Commun., No. 5, 191 (1995).Google Scholar
  201. 201.
    G. V. Ratovskii, S. L. Belaya, A. A. Tolmachev, and A. N. Kostyuk, Zh. Obshch. Khim., 62, 2046 (1992).Google Scholar
  202. 202.
    G. I. Zhungietu and G. N. Dorofeenko, Usp. Khim., 41, 1627 (1972).Google Scholar
  203. 203.
    N. N. Suvorov, Zh. Vses. Khim. Obshch. D. I. Mendeleeva, 21, 144 (1976).Google Scholar
  204. 204.
    B. Pullman and A. Pullman, Quantum Biochemistry [Russian translation], Mir, Moscow (1965), p. 654.Google Scholar
  205. 205.
    A. Sent-D'erd'i, Introduction to Submolecular Biology, Nauka, Moscow (1964), p. 139.Google Scholar
  206. 206.
    D. F. Downing, Quart. Rev., 16, 133 (1962).Google Scholar
  207. 207.
    N. N. Yarovenko, Zh. Vses. Khim. Obshch. D. I. Mendeleeva, 4, 448 (1964).Google Scholar
  208. 208.
    B. G. van den Bos, C. J. Schoot, M. J. Koopmans, and J. Meltzer, Rec. Trav. Chim., 80, 1040 (1961).Google Scholar
  209. 209.
    J. Meltzer, K. Wellinda, and B. G. van den Boss, US Patent 3111525; Chem. Abstr., 60, 9285 (1964).Google Scholar
  210. 210.
    C. van den Mestering and H. Veldstra, Rec. Trav. Chim., 77, 1096 (1958).Google Scholar
  211. 211.
    V. P. Shamshin, V. F. Shner, and N. N. Suvorov, Khim. Geterotsikl. Soedin., 498 (1972).Google Scholar
  212. 212.
    N. N. Suvorov, V. A. Chernov, L. M. Morozovskaya, and S. M. Volodarskaya, USSR Inventor's Certificate 168294; Byull. Izobr., No. 4 (1965).Google Scholar
  213. 213.
    L. M. Morozovskaya, N. N. Suvorov, M. A. Kolesnikova, V. A. Chernov, and S. M. Volodarskaya, Chemistry of Organic Compounds of Phosphorus [in Russian], Nauka, Leningrad (1967), p. 223.Google Scholar
  214. 214.
    K. C. Tsou, H. C. F. Su, D. Rabiger, H. Heymann, and A. M. Seligman, J. Med. Chem., 10, 662 (1967).Google Scholar
  215. 215.
    J. P. Horwitz, C. V. Easwaran, and P. L. Volf, Biochim. Biophys. Acta (E), 276, 206 (1972).Google Scholar
  216. 216.
    S. Umezawa, K. Tatsuta, O. Izawa, and T. Tsuchija, Tetrahedron Lett., 97 (1972).Google Scholar
  217. 217.
    V. N. Konyukhov, T. A. Bandurina, G. M. Anoshina, and Z. V. Pushkareva, Chemotherapy of Tumors in the USSR [in Russian], Sb. Ural'skogo Politekhn. In-ta, No. 25-26, 45 (1978).Google Scholar
  218. 218.
    T. A. Bandurina, V. N. Konyukhov, and A. A. Koltysheva, Chemotherapy of Tumors in the USSR [in Russian], Sb. Ural'skogo Politekhn. In-ta, No. 31, 160 (1980).Google Scholar
  219. 219.
    U. Katsuko, I. Shiro, and A. Sanya, Chem. Pharm. Bull., 22, 1918 (1974).Google Scholar
  220. 220.
    A. Burger and H. Shelver, J. Med. Pharm. Chem., 4, 225 (1961).Google Scholar
  221. 221.
    H. Pohlemann and R. Windels, British Patent 869339; Chem. Abstr., 56, 10104 (1962).Google Scholar
  222. 222.
    N. P. Grechkin, L. N. Grishina, I. D. Neklesova, M. A. Kudrina, and N. N. Anisimova, USSR Inventor's Certificate 430102; Byull. Izobr., No. 20 (1974).Google Scholar
  223. 223.
    N. P. Grechkin, L. N. Grishina, and G. A. Kashafutdinov, USSR Inventor's Certificate 524803; Byull. Izobr., No. 30 (1976).Google Scholar
  224. 224.
    N. P. Grechkin and L. N. Grishina, Izv. Akad. Nauk SSSR. Ser. Khim., 1670 (1973).Google Scholar
  225. 225.
    N. P. Grechkin and L. N. Grishina, Izv. Akad. Nauk SSSR. Ser. Khim., 1898 (1974).Google Scholar
  226. 226.
    N. P. Grechkin, L. N. Grishina, I. D. Neklesova, M. A. Kudrina, and N. N. Anisimova, USSR Inventor's Certificate 433152; Byull. Izobr., No. 23 (1974).Google Scholar
  227. 227.
    P. A. Gurevich, S. Yu. Baigil'dina, and G. I. Ruzal', Kazan, Dep. NIITEKHIM, No. 51-khp-85Dep. (1985).Google Scholar
  228. 228.
    P. A. Gurevich, A. I. Razumov, V. V. Moskva, T. V. Komina, G. Yu. Klimentova, and V. V. Kiselev, Abstracts of All-Union Conference of Chemical Means for the Protection of Plants [in Russian], Ufa (1982), p. 17.Google Scholar
  229. 229.
    Y. Jin and G. Just, Tetrahedron Lett., 39, 6433 (1998).Google Scholar
  230. 230.
    R. K. Sharma, S. S. Kohle, and R. S. Tripathi, Indian J. Agron., 39, 479 (1994).Google Scholar
  231. 231.
    S. P. Ivonin, A. A. Tolmachev, T. E. Terikovska, and A. M. Pinchuk, XII International Conference on Chemistry of Phosphorus Compounds [in Russian], Kiev (1999), p. 73.Google Scholar
  232. 232.
    A. A. Tolmachev and A. M. Pinchuk, XII International Conference on Chemistry of Phosphorus Compounds [in Russian], Kiev (1999), p. 138.Google Scholar
  233. 233.
    T. A. Bandurina, V. N. Konyukhov, and A. A. Koltysheva, Chemotherapy of Tumors in the USSR [in Russian], Sb. Ural'skogo Politekhn. In-ta, No. 36, 105 (1982).Google Scholar
  234. 234.
    G. L. Matevosyan and P. M. Zavlin, Zh. Obshch. Khim., 68, 1536 (1998).Google Scholar
  235. 235.
    I. V. Galkina, É. R. Zvereva, V. I. Galkin, A. A. Sobanov, and R. A. Cherkasov, Zh. Obshch. Khim., 68, 1453 (1998).Google Scholar

Copyright information

© Plenum Publishing Corporation 2000

Authors and Affiliations

  • P. A. Gurevich
    • 1
  • V. A. Yaroshevskaya
    • 1
  1. 1.Kazan State Technological UniversityKazanRussia

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