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Hetarylation of organic compounds (review)

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Chemistry of Heterocyclic Compounds Aims and scope

Abstract

Reactions of the direct introduction of nitrogenous aromatic heterocycles into nucleophilic organic compounds with the use in situ of N-acyl salts of heterocyclic cations and also of heteroaromatic anion radicals are discussed.

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Literature cited

  1. A. K. Sheinkman, S. I. Suminov, and A. N. Kost, Usp. Khim., 42, 1415 (1973).

    Google Scholar 

  2. M. Khamana, Khim. Geterotsikl. Soedin., 1155 (1973); Lectures in Heterocyclic Chemistry, 1, S-51 (1970).

  3. A. Treibs and H. Bader, Ber., 90, 789 (1957).

    Google Scholar 

  4. F. Krohnke and K. Dickoré, Ber., 92, 46 (1959).

    Google Scholar 

  5. A. K. Sheinkman, V.-A. Ivanov, and S. N. Baranov, Dopovidi AN URSR, 619 (1970).

  6. J. Claisen and E. Haase, Ber., 36, 3674 (1903).

    Google Scholar 

  7. W. Doering and W. McEwen, J. Amer. Chem. Soc., 72, 2104 (1951).

    Google Scholar 

  8. A. Reissert, Ber., 38, 1603, 3415 (1905).

    Google Scholar 

  9. W. McEwen and R. Cobb, Chem. Rev., 55, 511 (1955).

    Google Scholar 

  10. F. Popp, Adv. Heterocycl. Chem., 9, 1 (1968).

    Google Scholar 

  11. E. Koenigs and E. Ruppelt, Ann. Chem. 509, 142 (1934).

    Google Scholar 

  12. E. Chigi, Ber., 73, 677 (1940).

    Google Scholar 

  13. E. Chigi, Ber., 75, 764 (1942).

    Google Scholar 

  14. E. Chigi, Gazz. Chim. Ital., 76, 352 (1946).

    Google Scholar 

  15. W. McEwen, R. Terss, and J. Elliot, J. Amer. Chem. Soc., 74, 3605 (1952).

    Google Scholar 

  16. A. K. Sheinkman, Yu. N. Sheinker, S. L. Portnova, and A. N. Kost, Dokl. Akad. Nauk SSSR, 157, 1416 (1964).

    Google Scholar 

  17. G. Olah and P. Szilagyi, J. Amer. Chem. Soc., 91, 2949 (1969).

    Google Scholar 

  18. R. Paul, D. Singh, and S. Sandhu, J. Chem. Soc., 315 (1959).

  19. R. Paul, H. Khurana, S. Vasisht, and S. Chandra, J. Indian Chem. Soc., 46, 914 (1969).

    Google Scholar 

  20. J. Holečec, Sbornik Věd. Praci, Vysoká Škola Chem. Technol., Pardubice, 6, 19 (1965).

    Google Scholar 

  21. S. V. Bogatkov, V. V. Korshak, T. I. Mitaishvili, V. A. Vasnev, S. V. Vinogradova, and E. M. Cherkasova, Dokl. Akad. Nauk SSSR, 194, 328 (1970).

    Google Scholar 

  22. A. K. Sheinkman, Doctoral Dissertation, Rostov State University, Rostov-on-Don (1972).

    Google Scholar 

  23. V. E. Kononenko, T. N. Kashtanova, A. K. Sheinkman, and S. N. Baranov, Reakts. Sposobnost' Organ. Soedin., 8, 27 (1971).

    Google Scholar 

  24. A. Zoltewicz and L. Helmick, J. Amer. Chem. Soc., 92, 7547 (1970).

    Google Scholar 

  25. A. K. Sheinkman, L. M. Kapkan, L. G. Gakh, E. V. Titov, S. N. Baranov, and A. N. Kost, Dokl. Akad. Nauk SSSR, 193, 366 (1970).

    Google Scholar 

  26. E. M. Kosower, Progr. Phys. Org. Chem., 3, 81 (1965).

    Google Scholar 

  27. A. K. Sheinkman, T. V. Stupnikova, and A. A. Deikalo, Khim. Geterotsikl. Soedin., 1147 (1973).

  28. A. Nielsen, D. Moore, G. Muha, and K. Berry, J. Org. Chem., 29, 2175 (1964).

    Google Scholar 

  29. L. Winters, N. Smith, and M. Cohen, Chem. Comm., 642 (1970).

  30. J. Happ and E. Janzen, J. Org. Chem., 35, 96 (1970).

    Google Scholar 

  31. E. Janzen, J. Pickett, J. Happ, and W. De Angelis, J. Org. Chem., 35, 88 (1970).

    Google Scholar 

  32. K. Wallenfels and H. Schüly, Ann. Chem., 621, 86, 106, 166, 198 (1959).

    Google Scholar 

  33. D. Beke, Advan. Heterocycl. Chem., 1, 167 (1963).

    Google Scholar 

  34. A. K. Sheinkman, S. G. Potashnikova, and S. N. Baranov, Khim. Geterotsikl. Soedin., 563 (1969).

  35. A. K. Sheinkman, S. G. Potashnikova, and S. N. Baranov, Zh. Organ. Khim., 6, 614 (1970).

    Google Scholar 

  36. A. K. Sheinkman, S. G. Potashnikova, and S. N. Baranov, Methods of Obtaining Chemical Reagents and Preparations [in Russian], IREA, Moscow, Vol. 23 (1971), p. 49.

    Google Scholar 

  37. S. G. Potashnikova, Candidate's Dissertation, Donetsk (1971).

  38. A. K. Sheinkman, S. G. Potashnikova, and S. N. Baranov, Khim. Geterotsikl. Soedin., 1292 (1970).

  39. A. K. Sheinkman, A. N. Kost, S. G. Potashnikova, A. O. Ginzburg, and S. N. Baranov, Khim. Geterotsikl. Soedin., 648 (1971).

  40. A. K. Sheinkman and A. A. Deikalo, Khim. Geterotsikl. Soedin., 126 (1970).

  41. A. K. Sheinkman, A. A. Deikalo, T. V. Stupnikova, N. A. Klyuev, and G. A. Mal'tseva, Khim. Geterotsikl. Soedin., 1099 (1972).

  42. A. A. Deikalo, A. K. Sheinkman, and S. N. Baranov, Khim. Geterotsikl. Soedin., 1359 (1972).

  43. A. K. Sheinkman, A. A. Deikalo, T. V. Stupnikova, and S. N. Baranov, Khim. Geterotsikl. Soedin., 284 (1972).

  44. A. K. Sheinkman, G. V. Samoilenko, and S. N. Baranov, Zh. Obshch. Khim., 6, 2339 (1970).

    Google Scholar 

  45. A. A. Deikalo, Candidate's Dissertation, Donetsk (1971).

  46. H. von Dobeneck and W. Goltsche, Ber., 95, 1484 (1962).

    Google Scholar 

  47. J. Bergman, J. Heterocycl. Chem., 7, 1071 (1970).

    Google Scholar 

  48. A. K. Sheinkman, N. F. Kazarinova, and E. P. Babin, Zh. Vses. Khim. Obshchestva im. D. I. Mendeleeva, 7, 112 (1962).

    Google Scholar 

  49. A. K. Sheinkman, N. F. Kazarinova, and E. P. Babin, Author's Certificate No. 147, 187; Byul. Izobret., No. 10 (1962).

  50. A. K. Sheinkman, Candidate's Dissertation, Moscow (1964).

  51. A. N. Kost, A. K. Sheinkman, and N. F. Kazarinova, Zh. Obshch. Khim., 34, 2044 (1964).

    Google Scholar 

  52. A. N. Kost, A. K. Sheinkman, and A. N. Prilepskaya, Khim. Geterotsikl. Soedin., Collection 1 [in Russian] (1967), p. 248.

  53. A. K. Sheinkman, A. N. Kost, A. N. Prilepskaya, and Zh. V. Shiyan, Zh. Organ. Khim., 4, 1286 (1968).

    Google Scholar 

  54. A. K. Sheinkman, A. K. Tokarev, and S. N. Baranov, Khim. Geterotsikl. Soedin., 82 (1971).

  55. A. K. Sheinkman, A. P. Kucherenko, and S. N. Baranov, Khim. Geterotsikl. Soedin., 669 (1972).

  56. A. K. Sheinkman, A. K. Tokarev, A. P. Kucherenko, S. G. Potashnikova, A. A. Deikalo, and S. N. Baranov, Khim. Geterotsikl. Soedin., 643 (1971).

  57. A. N. Prilepskaya, Candidate's Dissertation, Donetsk (1971).

  58. A. K. Sheinkman and Yu. N. II'ina, Khim. Geterotsikl. Soedin., 568 (1971).

  59. O. Dimroth and R. Heene, Ber., 54, 2934 (1921).

    Google Scholar 

  60. O. Dimroth and F. Fister, Ber., 55, 1223, 3693 (1922).

    Google Scholar 

  61. A. E. Arbuzov, Izv. Akad. Nauk SSSR, Ser. Khim., 451 (1945).

  62. J. Wibaut, Rec. Trav. Chim., 60, 119 (1941).

    Google Scholar 

  63. M. K. Polievktov, A. K. Sheinkman, and L. N. Morozova, Khim. Geterotsikl. Soedin., 1067 (1973).

  64. A. K. Sheinkman and A. K. Tokarev, Zh. Organ. Khim., 7, 855 (1971).

    Google Scholar 

  65. A. K. Sheinkman, A. K. Tokarev, and A. N. Prilepskaya, Khim. Geterotsikl. Soedin., 529 (1972).

  66. M. V. Vol'pin and I. S. Akhrem, Dokl. Akad. Nauk SSR, 161, 597 (1965).

    Google Scholar 

  67. K. Conrow, J. Amer. Chem. Soc., 81, 5461 (1959).

    Google Scholar 

  68. F. Kröhnke and J. Vogt, Ann. Chem., 600, 211 (1956).

    Google Scholar 

  69. K. A. Grob, in: Theoretical Organic Chemistry, Butterworth's Scientific Publications, London (1959).

    Google Scholar 

  70. A. K. Sheinkman, A. N. Prilepskaya, and A. N. Kost, Khim. Geterotsikl. Soedin., 1515 (1970).

  71. A. A. Deikalo, A. K. Sheinkman, and S. N. Baranov, Khim. Geterotsikl. Soedin., 1359 (1972).

  72. F. Popp, W. Blount, and P. Melvin, J. Org. Chem., 26, 4930 (1961).

    Google Scholar 

  73. A. K. Sheinkman and A. N. Prilepskaya, Khim. Geterotsikl. Soedin., 1148 (1971).

  74. A. K. Sheinkman and A. N. Prilepskaya, Khim. Geterotsikl. Soedin., 860 (1971).

  75. A. K. Sheinkman, A. N. Prilepskaya, and R. D. Bondarchuk, USSR Authors' Certificate No. 188,496; Byul. Izobret, No. 22 (1966).

  76. A. K. Sheinkman and A. K. Tokarev, Khim. Geterotsikl. Soedin., 956 (1969).

  77. A. K. Sheinkman, A. K. Tokarev, S. N. Baranov, and A. N. Kost, USSR Authors' Certificate No. 253,805; Byul. Izobret., No. 37 (1969).

  78. A. K. Sheinkman, A. P. Kucherenko, and S. N. Baranov, Khim. Geterotsikl. Soedin., 1291 (1970).

  79. A. K. Tokarev, L. N. Volovel'skii, A. K. Sheinkman, and S. N. Baranov, Zh. Obshch. Khim., 92, 460 (1972).

    Google Scholar 

  80. A. K. Sheinkman, S. G. Potashnikova, and S. N. Baranov, Author's Certificate No. 292,479; Byul. Izobret., No. 29 (1971).

  81. A. K. Sheinkman, S. G. Potashnikova, and S. N. Baranov, Author's Certificate No. 327,197; Byul. Izobret., No. 5 (1972).

  82. A. K. Sheinkman and S. G. Potashnikova, Methods of Obtaining Chemical Reagents and Preparations [in Russian], IREA, Vol. 23, Moscow (1971), pp. 49, 77, 137.

    Google Scholar 

  83. J. Bergman, Tetrahedron Lett., 4723 (1972).

  84. T. V. Stupnikova, V. I. Sokolov, A. F. Pozharskii, and A. K. Sheinkman, Proceedings of the IInd Symposium on the Chemistry and Technology of the Heterocyclic Compounds of Combustible Minerals [in Russian], Donetsk (1973).

  85. A. K. Sheinkman, A. N. Kost, A. N. Prilepskaya, and N. A. Klyuev, Khim. Geterotsikl. Soedin., 1105 (1972).

  86. B. I. Stepanov and G. I. Migachev, Zh. Obshch. Khim., 35, 2254 (1965).

    Google Scholar 

  87. B. I. Stepanov and G. I. Migachev, Zh. Obshch. Khim., 36, 1447 (1966).

    Google Scholar 

  88. A. K. Sheinkman, G. V. Samoilenko, and S. N. Baranov, Proceedings of the 5th Conference on Organophosphorus Compounds [in Russian], Moscow (1972).

  89. B. I. Stepanov and G. I. Migachev, Zh. Vses. Khim. Obshch. im. D. I. Mendeleeva, 10, 712 (1965).

    Google Scholar 

  90. G. I. Migachev and B. I. Stepanov, Zh. Obshch. Khim., 38, 1368 (1968).

    Google Scholar 

  91. A. K. Sheinkman, A. N. Prilepskaya, O. A. Ginzburg, A. K. Tokarev, and A. A. Deikalo, Khim. Geterotsikl. Soedin., 421 (1971).

  92. A. N. Kost, A. K. Sheinkman, and N. F. Kazarinova, Khim. Geterotsikl. Soedin., 722 (1966).

  93. H. Fischer and P. Ernst, Ber., 59, 138 (1926).

    Google Scholar 

  94. A. Treibs and A. Ohorodnik, Ann. Chem., 611, 149 (1958).

    Google Scholar 

  95. A. Treibs and A. Dietl, Ann. Chem., 619, 80 (1958).

    Google Scholar 

  96. H. Plieninger, U. Lerch, and J. Kurze, Angew. Chem., 75, 724 (1963).

    Google Scholar 

  97. A. K. Sheinkman, A. N. Kost, and R. D. Bondarchuk, Author's Certificate No. 202,143; Byul. Izobret., No. 19 (1967).

  98. A. K. Sheinkman and A. A. Deikalo, Khim. Geterotsikl. Soedin., 1654 (1971).

  99. A. Treibs and M. Eligge, Ann. Chem., 652, 176 (1962).

    Google Scholar 

  100. A. K. Sheinkman, A. A. Deikalo, A. P. Kucherenko, and S. N. Baranov, Khim. Geterotsikl. Soedin., 424 (1971).

  101. A. K. Sheinkman and A. A. Deikalo, Methods of Obtaining Chemical Reagents and Preparations [in Russian], IREA, Vol. 23, Moscow (1971), p. 24.

    Google Scholar 

  102. S. Clementi, F. Cenel, and G. Marino, Chem. Comm., 498 (1967).

  103. A. G. Kamrad and A. I. Shatenshtein. Izv. Akad. Nauk LatvSSR. Ser. Khim., 507 (1963).

  104. A. I. Shatenshtein, A. G. Kamrad, I. O. Shapiro, Yu. I. Ranneva, and E. N. Zvyagintseva. Dokl. Akad. Nauk SSSR, 168, 364 (1966).

    Google Scholar 

  105. A. I. Shatenshtein, N. N. Magdesieva, Yu. I. Ranneva, I. O. Shapiro, and A. I. Serebryanskaya, Teoret. Éksperim. Khim., 3, 343 (1967).

    Google Scholar 

  106. S. McElvain and D. Kundiger, J. Amer. Chem. Soc., 64, 254 (1942).

    Google Scholar 

  107. P. Wright and W. McEwen, J. Amer. Chem. Soc., 76, 4540 (1959).

    Google Scholar 

  108. L. N. Volovel'skii, A. Ya. Yakovleva, A. K. Sheinkman, and A. K. Tokarev, Zh. Obshch. Khim., 43, 1414 (1973).

    Google Scholar 

  109. A. K. Sheinkman, A. K. Tokarev, and L. N. Volovel'skii, Author's Certificate No. 318,575; Byul. Izobret., No. 32 (1972).

  110. A. K. Sheinkman, G. V. Samoilenko, and S. N. Baranov, Zh. Obshch. Khim., 40, 2339 (1970).

    Google Scholar 

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

    Google Scholar 

  112. A. K. Sheinkman, G. V. Samoilenko, and S. N. Baranov, Author's Certificate No. 281,468; Byul. Izobret., No. 29 (1970).

  113. G. V. Samoilenko and P. A. Gurevich, Proceedings of the 2nd Symposium on the Chemistry and Technology of the Heterocyclic Compounds of Combustible Minerals [in Russian], Donetsk (1973).

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

    Google Scholar 

  115. A. K. Sheinkman, G. V. Samoilenko, and S. N. Baranov, Dokl. Akad. Nauk SSSR, 196, 137 (1971).

    Google Scholar 

  116. A. K. Sheinkman, V. A. Ivanov, N. A. Klyuev, and G. A. Mal'tseva, Zh. Organ. Khim., 9, 2550 (1973).

    Google Scholar 

  117. A. K. Sheinkman, V. A. Ivanov, and S. N. Baranov, Author's Certificate No. 276,960; Byul. Izobret., No. 24 (1970).

  118. A. K. Sheinkman, V. A. Ivanov, and S. N. Baranov, Author's Certificate No. 301,334; Byul. Izobret., No. 14 (1971).

  119. A. K. Sheinkman, V. A. Ivanov, and S. N. Baranov, Author's Certificate No. 259,887; Byul. Izobret., No. 3 (1970).

  120. A. K. Sheinkman, S. G. Potashnikova, and S. N. Baranov, Zh. Organ. Khim., 7, 1550 (1971).

    Google Scholar 

  121. B. Emmert and E. Asendorf, Ber., 72, 1188 (1939).

    Google Scholar 

  122. R. Abramovitch and A. Vinutha, J. Chem. Soc., C, 2104 (1969).

  123. A. P. Terent'ev and L. A. Yanovskaya, Reactions and Methods of Investigating Organic Compounds [in Russian], Khimiya, Vol. 5, Moscow (1957), p. 256.

    Google Scholar 

  124. G. Badger and W. Sasse, Advan. Heterocyclic Chem., 2, 179 (1963).

    Google Scholar 

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    A. K. Sheinkman

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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 1, pp. 3–18, January, 1974.

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Sheinkman, A.K. Hetarylation of organic compounds (review). Chem Heterocycl Compd 10, 1–13 (1974). https://doi.org/10.1007/BF00475897

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