Skip to main content
SpringerLink
Log in

Phosphorylated pyridines and their benzo-homologs (review)

  • Published:
Chemistry of Heterocyclic Compounds Aims and scope

Abstract

Methods are discussed for the phosphorylation of pyridines and their benzo-homologs to give compounds containing P-Het or P-CH2Het bonds. The chemical properties of these compounds are considered.

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

Literature Cited

  1. D. Redmore, Chem. Rev., 71, 315 (1971).

    Google Scholar 

  2. G. L. Matevosyan and P. M. Zavlin, Zh. Obshch. Khim., 52, 1441 (1982).

    Google Scholar 

  3. A. I. Razumov, P. A. Gurevich, and S. Yu. Baigil'dina, Khim. Geterotsikl. Soedin., No. 7, 867 (1976).

    Google Scholar 

  4. é. E. Nifant'ev, in: The Chemistry of Hydrophosphoryl Compounds [in Russian], Nauka, Moscow (1983), p. 53.

    Google Scholar 

  5. W. S. Wadsworth, in: Organic Reactions, Wiley-Interscience, New York-London-Sydney-Toronto, Vol. 25 (1973), p. 73.

    Google Scholar 

  6. H. L. Yale, in: Heterocyclic Compounds, E. Klingsberg (ed.), Interscience, New York-London-Sydney, Vol. 14, Part 4 (1964), p. 425.

    Google Scholar 

  7. A. S. Sadykov, D. N. Dalimov, and N. N. Godovikov, Usp. Khim., 52, 1602 (1983).

    Google Scholar 

  8. D. Redmore, J. Org. Chem., 34, 1420 (1969).

    Google Scholar 

  9. A. K. Sheinkman, G. V. Samoilenko, and S. N. Baranov, Zh. Obshch. Khim., 40, 700 (1970).

    Google Scholar 

  10. D. Redmore, J. Org. Chem., 35, 4114 (1970).

    Google Scholar 

  11. D. Redmore, J. Org. Chem., 38, 1306 (1973).

    Google Scholar 

  12. D. Redmore, US Patent No. 3,770,750; Ref. Zh. Khim., 1974, 22N213.

  13. D. Redmore, US Patent No. 3,786,055; Ref. Zh. Khim., 1974, 23N233.

  14. D. Redmore, US Patent No. 3,810,907; Ref. Zh. Khim., 1975, 90424.

  15. D. A. Predvoditelev, T. G. Chubakur, and é. E. Nifant'ev, Khim. Geterotsikl. Soedin., No. 3, 377 (1975).

    Google Scholar 

  16. V. N. Eliseeva, N. V. Bureva, and B. E. Ivanov, Khim. Geterotsikl. Soedin., No. 10, 1354 (1974).

    Google Scholar 

  17. A. K. Sheinkman, G. V. Samoilenko, and S. N. Baranov, Dokl. Akad. Nauk SSSR, 196, 13 (1971).

    Google Scholar 

  18. A. K. Sheinkman, G. V. Samoilenko, and S. N. Baranov, USSR Inventor's Certificate No. 281,468; Byull. Izobret., No. 29, 39 (1970).

  19. A. K. Sheinkman, G. V. Samoilenko, and S. N. Baranov, in: The Chemistry and Application; of Organophosphorus Compounds [in Russian], Nauka, Moscow (1974), p. 366.

    Google Scholar 

  20. K. Akiba, Y. Negishi, and N. Inamoto, Synthesis, No. 1, 55 (1979).

    Google Scholar 

  21. K. Akiba, T. Kasai, and M. Wada, Tetrahed. Lett., 23, 1709 (1982).

    Google Scholar 

  22. K. Akiba, N. Inamoto, Y. Negishi, and K. Kurumaya, Heterocycles, 16, 143 (1981).

    Google Scholar 

  23. K. Akiba, H. Matsuoka, and M. Wada, Tetrahed. Lett., 22, 4093 (1981).

    Google Scholar 

  24. K. Akiba, Y. Negishi, K. Kuruyama, N. Vegama, and N. Inamoto, Tetrahed. Lett., 22, 4977 (1981).

    Google Scholar 

  25. Y. Hamada, I. Takeuchi, and A. Shibata, Heterocycles, 21, 487 (1984).

    Google Scholar 

  26. I. Takeuchi, A. Shibata, and Y. Hamada, Yakugaku Zasshi, 104, 1133 (1984).

    Google Scholar 

  27. I. Takeuchi, A. Shibata, and Y. Hamada, Heterocycles, 23, 185 (1985).

    Google Scholar 

  28. K. Akiba, Y. Negishi, and N. Inamoto, Bull. Chem. Soc. Jpn., 57, 2188 (1984).

    Google Scholar 

  29. K. Akiba, Y. Negishi, and N. Inamoto, Bull. Chem. Soc. Jpn., 57, 2333 (1984).

    Google Scholar 

  30. A. R. Katritzky, J. Keay, and M. P. Sammes, J. Chem. Soc., Perkin 1, No. 3, 668 (1981).

    Google Scholar 

  31. K. Akiba, K. Ishikawa, and N. Inamoto, Synthesis, No. 12, 862 (1977).

    Google Scholar 

  32. K. Ishikawa, K, Akiba, and N. Inamoto, Bull. Chem. Soc. Jpn., 51, 2684 (1978).

    Google Scholar 

  33. D. Redmore, US Patent No. 3,880,815; Ref. Zh. Khim., 120522 (1975).

  34. J. Carey and J. R. Case, J. Chem. Soc., Perkin 1, No. 10, 2429 (1977).

    Google Scholar 

  35. D. Redmore, J. Org. Chem., 41, 2148 (1976).

    Google Scholar 

  36. D. Redmore, US Patent No. 4,187,378; Ref. Zh. Khim., 22N165 (1980).

  37. B. Boduszek and Mek Y. Wiecz, Synthesis, No. 6, 452 (1979).

    Google Scholar 

  38. B. Boduszek and Mek Y. Wiecz, Polish Patent No. 105,890; Ref. Zh. Khim., 23023 (1980).

  39. B. Boduszek and Mek Y. Wiecz, Synthesis, No. 6, 454 (1979).

    Google Scholar 

  40. A. Burger, J. B. Clements, N. D. Dawson, and R. B. Henderson, J. Org. Chem., 20, 1383 (1955).

    Google Scholar 

  41. B. A. Arbuzov and B. P. Lugovkin, Zh. Obshch. Khim., 22, 1199 (1952).

    Google Scholar 

  42. G. M. Kosolapoff, J. Am. Chem. Soc., 67, 1002 (1947).

    Google Scholar 

  43. Ya. N. Ivashchenko, L. D. Sologub, S. D. Moshchitskii, and A. V. Kirsanov, Zh. Obshch. Khim., 39, 1695 (1969).

    Google Scholar 

  44. J. Bratt and H. Suschitzky, J. Chem. Soc., Perkin 1, No. 8, 1689 (1973).

    Google Scholar 

  45. W. Boenigk and G. HÄgele, Chem. Ber., 116, 2418 (1983).

    Google Scholar 

  46. W. Boenigk, U. Fischer, and G. HÄgele, Phosph. Sulf., 16, 263 (1983).

    Google Scholar 

  47. S. D. Moshchitskii, L. D. Sologub, A. F. Pavlenko, and V. P. Kuhar', Zh. Obshch. Khim., 47, 1263 (1977).

    Google Scholar 

  48. L. N. Markovskii, G. G. Furin, Yu. G. Shermolovich, and G. G. Yakobson, Zh. Obshch. Khim., 49, 531 (1979).

    Google Scholar 

  49. L. N. Markovskii, G. G. Furin, Yu. G. Shermolovich, and G. G. Yakobson, Izd. Akad. Nauk SSSR, Ser. Khim., No. 12, 2839 (1977).

    Google Scholar 

  50. L. Achremowicz, Synthesis, No. 10, 653 (1975).

    Google Scholar 

  51. L. Kato, N. Katagivi, and A. Wagai, Chem. Pharm. Bull., 29, 1069 (1981); Ref. Zh. Khim., 3Zh245 (1982).

    Google Scholar 

  52. A. K. Bhattacharya and G. Thyagarajan, Chem. Rev., 81, 415 (1981).

    Google Scholar 

  53. J. I. G. Cadogan, D. S. Sears, and P. M. Smit, J. Chem. Soc., C, No. 6, 1314 (1969).

    Google Scholar 

  54. I. N. Zhmurova, I. N. Kosinskaya, and A. M. Pinchuk, Zh. Obshch. Khim., 51, 158 (1981).

    Google Scholar 

  55. M. A. Weiner and U. A. Bas, Inorg. Chem., 19, 2797 (1980).

    Google Scholar 

  56. L. Horner and H. Hoffman, Chem. Ber., 91, 50 (1958).

    Google Scholar 

  57. Yu. M. Kargin, E. V. Nikitin, O. V. Paratin, Yu. A. Ignat'ev, A. S. Romanikhin, G. V. Romanov, T. Ya. Stepanova, and A. N. Pudovik, Izv. Akad. Nauk SSSR, Ser. Khim., No. 4, 939 (1980).

    Google Scholar 

  58. A. F. Shivanyuk, M. O. Lozinskii, and V. N. Kalinin, Zh. Obshch. Khim., 52, 704 (1982).

    Google Scholar 

  59. Yu. A. Sokolova, O. A. D'yachenko, L. O. Atovmyan, M. O. Lozinskii, and A. F. Shivanyuk, Izv. Akad. Nauk SSSR, Ser. Khim., No. 4, 815 (1983).

    Google Scholar 

  60. M. Regitz, W. Disteldorf, U. Eckstein, and B. Weber, Tetrahed. Lett., No. 30, 3979 (1972).

    Google Scholar 

  61. D. Redmore, Phosph. Sulf., 5, 271 (1978).

    Google Scholar 

  62. J. S. Loran, R. A. Naylor, and A. Williams, J. Chem. Soc., Perkin 2, No. 10, 1444 (1976).

    Google Scholar 

  63. G. R. Newkome and D. C. Hager, J. Am. Chem. Soc., 100, 5567 (1978).

    Google Scholar 

  64. E. Zbiral, in: Organophosphorus Reagents in Organic Synthesis, J. I. G. Cadogan (ed.), Interscience, London-New York-Sydney (1979), p. 223.

    Google Scholar 

  65. K. Akiba, N. Yoshio, and I. Naoki, Chem. Lett., No. 3, 349 (1982); Ref. Zh. Khim., 22E100 (1982).

    Google Scholar 

  66. E. Plazck and Z. Sesyk, Roczn. Chem., 14, 98 (1934).

    Google Scholar 

  67. R. D. Bennett, A. Burger, and W. A. Volk, J. Org. Chem., 23, 940 (1958).

    Google Scholar 

  68. E. Bunel, R. J. Manzv, and T. J. Retver, J. Chem. Res. Synop., 9, 285 (1981); Ref. Zh. Khim., 8Zh679 (1982).

    Google Scholar 

  69. K. V. Vatsuro and G. L. Mishchenko, Named Reactions in Organic Chemistry [in Russian], Khimiya, Moscow (1976), p. 247.

    Google Scholar 

  70. D. J. Collins, J. W. Heterington, and J. M. Swan, Austral. J. Chem., 27, 1355 (1974).

    Google Scholar 

  71. T. Hirao, T. Masunaga, Y. Oshiro, and T. Agawa, Synthesis, No. 1, 56 (1981).

    Google Scholar 

  72. L. D. Quin, M. P. Gordon, and J. E. MacDiarmid, J. Heterocycl. Chem., 19, 1041 (1982).

    Google Scholar 

  73. L. D. Kvin (Quin), D. E. Makdiarmid (MacDiarmid), E. D. Middlmas (Middlemas), and U. L. Orton, in: The Chemistry and Uses of Organophosphorus Compounds [Russian translation], A. V. Kirsanov (ed.), Naukova Dumka, Kiev (1981), p. 131.

    Google Scholar 

  74. H. J. Bestmann, G. Schmid, R. Bohme, E. Wilhelm, and H. Burzlaff, Chem. Ber., 113, 3937 (1980).

    Google Scholar 

  75. A. Yu. Alikin, M. P. Sokolov, B. G. Lirbech, A. I. Razumov, T. V. Zykova, and V. V. Zykova, Zh. Obshch. Khim., 51, 547 (1981).

    Google Scholar 

  76. A. Yu. Alikin, M. P. Sokolov, B. G. Lirbech, A. I. Razumov, T. V. Zykova, and V. V. Zykova, Zh. Obshch. Khim., 51, 556 (1981).

    Google Scholar 

  77. V. V. Kormachev, T. V. Vasil'eva, B. I. Ionin, and V. A. Kukhtin, Zh. Obshch. Khim., 45, 307 (1975).

    Google Scholar 

  78. é. S. Kozlov, A. A. Tolmachev, Yu. L. Slominskii, and A. M. Pinchuk, Khim. Geterotsikl Soedin., No. 3, 416 (1982).

    Google Scholar 

  79. A. A. Tolmachev, é. S. Kozlov, and A. M. Pinchuk, Zh. Obshch. Khim., 52, 2352 (1982).

    Google Scholar 

  80. A. A. Tolmachev, é. S. Kozlov, and A. M. Pinchuk, Zh. Obshch. Khim., 53, 1553 (1983).

    Google Scholar 

  81. G. M. Kosolapoff, J. Org. Chem., 21, 1046 (1956).

    Google Scholar 

  82. V. A. Kukhtin, R. P. Pavlov, V. V. Kormachev, and A. V. Kazymov, USSR Inventor's Certificate No. 713,869; Ref. Zh. Khim., 16N275 (1980).

  83. M. I. Shevchuk, I. V. Megera, V. N. Kushnir, and O. M. Bukinchik, in: Named Reactions in Organic Chemistry [in Russian], Khimiya, Moscow, p. 326.

  84. A. A. Tolmachev, é. S. Kozlov, A. D. Kachkovskii, and Yu. L. Slominskii, Zh. Obshch. Khim., 55, 566 (1985).

    Google Scholar 

  85. P. I. Yagodinets, Author's Abstract of Candidate's Dissertation, Chernovitskii Univ. (1983).

  86. E. Maruszewska-Wieczorkowska, J. Michalski, and A. Skowronska, Roczn. Chem., 28, 1197 (1956).

    Google Scholar 

  87. R. Bodalski, M. Pietrusiewicz, P. Majewski, and J. Michalski, Collect. Czech. Chem. Commun., 36, 4079 (1971).

    Google Scholar 

  88. R. Bodalski, A. Malkiwsz, and J. Michalski, Bull. Acad. Polon. Sci., 13, 139 (1965).

    Google Scholar 

  89. N. A. Hane, C. Wata, and D. E. Metzler, J. Med. Chem., 23, 595 (1983).

    Google Scholar 

  90. E. Maruszewska-Wieczorkowska, and J. Michalski, Roczn. Chem., 38, 623 (1964).

    Google Scholar 

  91. P. Bdnarek, R. Bodalski, and J. Michalski, Bull. Acad. Polon. Sci., 11, 507 (1963).

    Google Scholar 

  92. V. Jagodic, B. Bozik, L. Tusek-Bozik, and M. J. Herak, J. Het. Chem., 17, 685 (1980).

    Google Scholar 

  93. B. P. Lugovkin, Zh. Obshch. Khim., 27, 529 (1957).

    Google Scholar 

  94. M. I. Shevchuk, I. P. Chernyuk, E. N. Volynskaya, V. V. Shelest, and P. I. Yagodinets, Zh. Obshch. Khim., 50, 1978 (1980).

    Google Scholar 

  95. B. A. Khaskin, in: Reactions and Methods of Study of Organic Compounds [in Russian], B. A. Kazanskii and I. L. Knunyants (eds.), Khimiya, Moscow (1969), p. 131.

    Google Scholar 

  96. U. Horn, F. Mutterer, and C. D. Weis, Helv. Chim. Acta, 59, 190 (1976).

    Google Scholar 

  97. K. Fuji, K. Ichikawa, and E. Fujita, Tetrahed. Lett., No. 4, 361 (1979).

    Google Scholar 

  98. P. Carsky, S. Hunig, I. Stemmler, and D. Scheutsow, Liebigs. Ann., No. 2, 291 (1980).

    Google Scholar 

  99. H. Schmidbaur and V. Deschler, Chem. Ber., 114, 2491 (1981).

    Google Scholar 

  100. H. Schmidbaur, V. Deschler, and B. Milewski-Mahrla, Chem. Ber., 115, 3290 (1982).

    Google Scholar 

  101. B. B. Jarvis and B. A. Marien, J. Org. Chem., 42, 2676 (1977).

    Google Scholar 

  102. M. A. Weiner and P. Schwartz, Inorg. Chem., 14, 1714 (1975).

    Google Scholar 

  103. I. K. Chernyuk, V. V. Shelest, M. Yu. Kornilov, and G. T. Pilyugin, Zh. Obshch. Khim., 45, 1559 (1975).

    Google Scholar 

  104. T. Kauffman and R. Joussen, Chem. Ber., 110, 3930 (1977).

    Google Scholar 

  105. F. S. Babichev, Yu. M. Volovenko, and V. S. Talanov, Dokl. Akad. Nauk SSSR, No. 6, 508 (1977).

    Google Scholar 

  106. F. S. Babichev and Yu. M. Volovenko, Ukr. Khim. Zh., 43, 41 (1977).

    Google Scholar 

  107. V. S. Abramov and A. S. Kapustina, Zh. Obshch. Khim., 24, 311 (1954).

    Google Scholar 

  108. B. P. Lugovkin, Khim. Geterotsikl. Soedin., No. 1, 117 (1968).

    Google Scholar 

  109. B. P. Lugovkin, Khim. Geterotsikl. Soedin., No. 5, 694 (1969).

    Google Scholar 

  110. H. Zimmer and J. P. Bercz, Liebigs Ann., 686, 107 (1965).

    Google Scholar 

  111. J. Lerch and A. Kottler, West German Patent No. 1,002,355; Chem. Abstr., 53, 21814 (1959).

    Google Scholar 

  112. N. Morita and S. I. Miller, J. Org. Chem., 42, 4245 (1977).

    Google Scholar 

  113. H. Koning, G. N. Mallo, A. Springer-Fidder, and H. O. Huisman, Rec. Trav. Chim., 92, 683 (1973).

    Google Scholar 

  114. C. Piechucki, Synthesis, No. 3, 869 (1974).

    Google Scholar 

  115. C. Piechucki, Synthesis, No. 9, 187 (1976).

    Google Scholar 

  116. M. Regits, Chem. Ber., 99, 2919 (1966).

    Google Scholar 

  117. M. Regits and C. Anschütz, Chem. Ber., 102, 2216 (1969).

    Google Scholar 

  118. C. W. Davies and F. G. Mann, J. Chem. Soc., No. 1, 276 (1944).

    Google Scholar 

  119. F. G. Mann and J. Watson, J. Org. Chem., 13, 502 (1948).

    Google Scholar 

  120. E. Plazek, Zeszyty, Nayk Politech. Wroclaw. Chem., 79 (1957); Chem. Abstr., 52, 20156 (1958).

    Google Scholar 

  121. G. E. Griffin and W. A. Thomas, J. Chem. Soc., B, No. 2, 477 (1970).

    Google Scholar 

  122. H. G. Ang, W. E. Kow, and K. F. Mok, Inorg. Nucl. Chem. Lett., 8, 829 (1972).

    Google Scholar 

  123. H. Schmidbaur and Y. Z. Inoguchi, Z. Naturforsch., 35, 1329 (1980).

    Google Scholar 

  124. Y. Inoguchi, B. Milewski-Mahrla, and H. Schmidbaur, Chem. Ber., 115, 3085 (1982).

    Google Scholar 

  125. K. Kurtev and D. Ribola, J. Chem. Soc., Dalton, No. 1, 55 (1980).

    Google Scholar 

  126. S. S. Dua, R. C. Edmondson, and H. Gilman, J. Organomet. Chem., 24, 703 (1970).

    Google Scholar 

  127. K. Issleib and M. Haftendorn, Z. Anorg. Chem., 376, 79 (1970).

    Google Scholar 

  128. W. V. Dahlhoff, T. R. Dick, and S. M. Nelson, J. Chem. Soc., A, No. 19, 2919 (1969).

    Google Scholar 

  129. W. V. Dahlhoff, G. H. Ford, W. S. J. Kelly, and S. M. Nelson, J. Chem. Soc., A, No. 21, 3495 (1971).

    Google Scholar 

  130. S. M. Nelson, M. Perks, and B. J. Walker, J. Chem. Soc., Perkin 1, No. 11, 1205 (1976).

    Google Scholar 

  131. B. Chiwell, Austral. J. Chem., 20, 2533 (1967).

    Google Scholar 

  132. A. J. Delmen, D. Rothwell, M. B. Hursthouse, and K. M. Abdul-Malic, J. Chem. Soc., Dalton, No. 20, 1974 (1980).

    Google Scholar 

  133. E. Shewchuk and S. B. Wild, J. Organomet. Chem., 210, 181 (1981).

    Google Scholar 

  134. K. Issleib and L. Brüschber, Z. Naturforsch., 20, 181 (1965).

    Google Scholar 

  135. R. Newkome and D. Hager, J. Org. Chem., 43, 947 (1978).

    Google Scholar 

  136. A. A. Tolmachev, é. S. Kozlov, and A. M. Pinchuk, Zh. Obshch. Khim., 54, 971 (1984).

    Google Scholar 

  137. R. D. Feltham and H. G. Metrger, J. Organomet. Chem., 33, 347 (1971).

    Google Scholar 

  138. D. G. Allen, G. M. Melanhein, G. B. Robertson, W. L. Steffen, G. Salem, and S. B. Wild, Inorg. Chem., 21, 1007 (1982).

    Google Scholar 

  139. R. A. Alonso, A. Bardon, and R. A. Rossi, J. Org. Chem., 49, 3584 (1984).

    Google Scholar 

  140. G. A. Barclay, C. M. Harris, and J. V. Kingston, Chem. Ind., No. 30, 227 (1965).

    Google Scholar 

  141. M. J. Callagher and F. G. Mann, J. Chem. Soc., No. 12, 5110 (1962).

    Google Scholar 

  142. M. J. Callagher and F. G. Mann, J. Chem. Soc., No. 10, 4855 (1963).

    Google Scholar 

  143. K. Dimroth and J. Hoffman, Chem. Ber., 99, 1325 (1966).

    Google Scholar 

  144. I. Kawada and R. Allman, Angew. Chem., 80, 40 (1968).

    Google Scholar 

  145. K. Dimroth, Fortschr. Chem. Forsch., 38, 7 (1973).

    Google Scholar 

  146. A. Schmidpeter, W. Gebler, F. Zwaschka, and W. S. Sheldrick, Angew. Chem., 92, 767 (1980).

    Google Scholar 

  147. J. M. Alcaraz, A. Breque, and F. Mathey, Tetrahed. Lett., 23, 1565 (1982).

    Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Institute of Organic Chemistry, Academy of Sciences of the Ukrainian SSR, 252660, Kiev

    A. A. Tolmachev & é. S. Kozlov

Authors
  1. A. A. Tolmachev
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. é. S. Kozlov
    View author publications

    You can also search for this author in PubMed Google Scholar

Additional information

Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 12, pp. 1587–1601, December, 1986.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Tolmachev, A.A., Kozlov, é.S. Phosphorylated pyridines and their benzo-homologs (review). Chem Heterocycl Compd 22, 1277–1291 (1986). https://doi.org/10.1007/BF00474345

Download citation

  • Received:

  • Revised:

  • Issue Date:

  • DOI: https://doi.org/10.1007/BF00474345

Keywords

Search

Navigation