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Reductive amination in the synthesis of azaheterocycles (review)

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Chemistry of Heterocyclic Compounds Aims and scope

Abstract

Methods for obtaining saturated five- and six-membered azaheterocycles based on the use of catalytic intra- and intermolecular hydroamination of dicarbonyl compounds and ketones and amines of the furan series, hydride amination of aldehydes and ketones, and the Leuckart reaction are examined.

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Literature Cited

  1. R. K. Hill, in: Chemistry of the Alkaloids, Van Nostrand, New York (1970), p. 385.

    Google Scholar 

  2. M. D. Mashkovskii, Medicinals [in Russian], Vol. 1, Meditsina, Moscow (1985), pp. 133, 135.

    Google Scholar 

  3. I. N. Klochkova, A. P. Kriven'ko, and M. V. Noritsina, Pyrrolidylalkanols [in Russian], Izd. Saratovsk. Univ., Saratov (1979).

    Google Scholar 

  4. V. Emerson, in: Organic Reactions [Russian translation], Vol. 5, Inostr. Lit., Moscow (1951), p. 347.

    Google Scholar 

  5. V. A. Nekrasova and N. I. Shuikin, Usp. Khim., 34, 1945 (1965).

    Google Scholar 

  6. M. I. Yukushkin, Khim. Promst., No. 7, 13 (1966).

    Google Scholar 

  7. P. Rylander, Catalytic Hydroamination over Platinum Metals, Academic Press, New York (1967).

    Google Scholar 

  8. B. M. Bogoslovskii, in: Reactions and Methods of Investigation of Organic Compounds [in Russian], Vol. 3, GNTIKhL, Moscow (1954), p. 225.

    Google Scholar 

  9. M. V. Klyuev and M. L. Khidekel', Usp. Khim., 49, 28 (1980).

    Google Scholar 

  10. M. V. Shimanskaya, Ya. F. Oshis, and A. A. Anderson, Khim. Geterotsikl. Soedin., No. 12, 1587 (1983).

    Google Scholar 

  11. M. G. Mignonac, Compt. Rend., 169, 237 (1919).

    Google Scholar 

  12. J. Jungers and L. Sajus, Kinetic Methods for the Investigation of Chemical Processes [Russian translation], Khimiya, Moscow (1972), p. 400.

    Google Scholar 

  13. G. A. Kliger, L. S. Glebov, V. A. Fridman, E. I. Bogolepova, and A. N. Bashkirov, Kinet. Katal., 19, 619 (1978).

    Google Scholar 

  14. N. S. Kozlov, V. A. Tarasevich, S. I. Kozintsev, and L. V. Gladkikh, Dokl. Akad. Nauk BSSR, 27, 634 (1983).

    Google Scholar 

  15. E. I. Hil'debrand and A. B. Fasman, Raney Catalysts in Organic Chemistry [Russian translation], Nauka, Alma-Ata (1982).

    Google Scholar 

  16. A. Skita and F. Keil, Chem. Ber., 62, 1142 (1929).

    Google Scholar 

  17. A. Skita and F. Keil, Angew. Chem., 42, 501 (1929).

    Google Scholar 

  18. V. G. Kharchenko, A. P. Kriven'ko, O. V. Fedotova, and T. G. Nikolaeva, Khim. Geterotsikl. Soedin., No. 7, 944 (1982).

    Google Scholar 

  19. T. G. Nikolaeva, P. V. Reshetov, A. P. Kriven'ko, and V. G. Kharchenko, Khim. Geterotsikl. Soedin., No. 10, 1370 (1983).

    Google Scholar 

  20. E. J. Schwoegler and H. Adkins, J. Am. Chem. Soc., 61, 3499 (1939).

    Google Scholar 

  21. N. S. Kozlov, in: Heterogeneous Catalysis in the Chemistry of Heterocyclic Compounds [in Russian], Zinatne, Riga (1981), p. 23.

    Google Scholar 

  22. N. S. Kozlov, L. I. Moiseenok, and S. I. Kozintsev, in: The Chemistry of Dicarbonyl Compounds [in Russian], Izd. Rizhsk. Politekh. Inst., Riga (1981), p. 114.

    Google Scholar 

  23. N. S. Kozlov, L. I. Moiseenok, and S. I. Kozintsev, Khim. Geterotsikl. Soedin., No. 11, 1483 (1979).

    Google Scholar 

  24. W. Z. Shilling, US Patent No. 3235562; Ref. Zh. Khim., 13N82 (1967).

  25. H. Vakamatsu and M. Takesada, Japanese Patent No. 23344; Ref. Zh. Khim., 12N210 (1975).

  26. A. A. Ponomarev and V. A. Sedavkina, USSR Inventor's Certificate No. 192820; Byull. Izobret., No. 6, 28 (1967).

  27. A. A. Ponomarev and V. A. Sedavkina, Khim. Geterotsikl. Soedin., No. 5, 809 (1969).

    Google Scholar 

  28. V. A. Sedavkina, I. V. Lizak, and L. K. Kulikova, Khim.-farm. Zh., No. 10, 34 (1978).

    Google Scholar 

  29. N. I. Shuikin, I. F. Bel'skii, V. M. Shostakovskii, S. N. Khor'kov, and G. K. Gaivoronskii, Dokl. Akad. Nauk SSSR, 153, 628 (1963).

    Google Scholar 

  30. Shu-Kung Chu and W. S. Lin, Hua Hsueh, Nos. 3–4, 65 (1970); Chem. Abstr., 74, 87732 (1971)

    Google Scholar 

  31. V. A. Sedavkina and N. A. Morozova, Khim. Geterotskikl. Soedin., No. 3, 331 (1972).

    Google Scholar 

  32. V. A. Sedavkina, N. A. Morozova, L. K. Kukokova and V. E. Murav'ev, Khim.-farm. Zh., No. 3 33 (1976).

    Google Scholar 

  33. V. A. Sedavkina and N. A. Morozova, USSR Inventor's. Certificate No. 574440; Byull. Izobret., No. 36, 63 (1977).

  34. V. A. Sedavkina and I. V. Lizak, USSR Inventor's Certificate No. 513972; Byull. Izobret., No. 18, 72 (1976).

  35. V. A. Sedavkina and G. V. Bespalova, USSR Inventor's Certificate No. 697505; Byull. Izobret., No. 42, 96 (1979).

  36. G. V. Bespalova and V. A. Sedavkina, in: Heterogeneous Catalysis in the Chemistry of Heterocyclic Compounds [in Russian], Zinatne, Riga (1981), p. 128.

    Google Scholar 

  37. V. A. Sedavkina, I. V. Lizak, L. K. Kulikova, and E. E. Ostroumova, Khim.-farm. Zh., No. 1, 54 (1984).

    Google Scholar 

  38. J. Greenstein and M. Winitz, Chemistry of the Amino Acids, Wiley (1961).

  39. R. B. Moffat, J. Org. Chem., 14, 862 (1949).

    Google Scholar 

  40. W. Reid, US Patent No. 2605266; Chem. Abstr., 47, 5451 (1953).

    Google Scholar 

  41. V. G. Bukharov and T. E. Pozdnyakova, Izv. Akad. Nauk SSSR, Ser. Khim., No. 6, 1108 (1960).

    Google Scholar 

  42. V. A. Sedavkina, N. A. Morozova, G. V. Bespalova, and I. V. Lizak, in: Collection of Lectures of the 3rd International Symposium on Furan Chenistry, Czechoslovakia (1979), p. 232.

  43. A. A. Ponomarev and V. A. Sedavkina, Khim. Geterotsikl. Soedin., No. 5, 809 (1969).

    Google Scholar 

  44. C. F. Winans, J. Am. Chem. Soc., 61, 3566 (1939).

    Google Scholar 

  45. A. A. Ponomarev, N. P. Maslennikova, N. V. Alakina, and A. P. Kriven'ko, Dokl. Akad. Nauk SSSR, 131, 1355 (1960).

    Google Scholar 

  46. A. A. Ponomarev, N. P. Maslennikova, and A. P. Kriven'ko, Zh. Obshch. Khim., 31, 958 (1961).

    Google Scholar 

  47. A. P. Kriven'ko, Candidate's Dissertation, Saratov (1967).

  48. N. I. Shuikin, A. D. Petrov, V. G. Glukhovtsev, I. F. Bel'skii, and G. E. Skobtsova, Izv. Akad. Nauk SSSR, Ser. Khim., No. 9, 1682 (1964).

    Google Scholar 

  49. B. V. Passet and V. Ya. Vorob'eva, The Technology of Pharmaceutical-Chemical Preparations and Antibiotics [in Russian], Meditsina, Moscow (1977), p. 282.

    Google Scholar 

  50. C. L. Wilson, J. Am. Chem. Soc., 67, 693 (1945).

    Google Scholar 

  51. A. A. Ponomarev, A. P. Kriven'ko, and M. V. Noritsina, Dokl. Akad. Nauk SSSR, 156, 102 (1964).

    Google Scholar 

  52. A. A. Ponomarev, M. V. Noritsina, and A. P. Kriven'ko, Khim. Geterotsikl. Soedin., No. 6, 923 (1966).

    Google Scholar 

  53. A. A. Ponomarev, A. P. Kriven'ko, and M. V. Noritsina, Khim. Geterotsikl. Soedin., No. 5, 850 (1967).

    Google Scholar 

  54. A. A. Ponomarev, A. P. Kriven'ko, and M. V. Noritsina, USSR Inventor's Certificate No. 158277; Byull. Izobret., No. 21, 15 (1963).

  55. A. A. Ponomarev, M. V. Noritsina, and A. P. Kriven'ko, USSR Inventor's Certificate No. 176961; Byull. Izobret., No. 24, 22 (1965).

  56. A. A. Ponomarev, A. P. Kriven'ko, and M. V., Noritsina, Khim. Geterotsikl. Soedin., No. 6, 787 (1970).

    Google Scholar 

  57. A. P. Krivenko and T. G. Nikolaeva (Nickolaeva), in: Collection of Lectures of the 3rd International Symposium on Furan Chemistry, Czechoslovakia (1979), p. 190.

  58. A. P. Kriven'ko and T. G. Nikolaeva, in: Materials of the 3rd All-Union Scientific Conference on the Chemistry and Technology of Furan Compounds [in Russian], Zinatne, Riga (1978), p. 119.

    Google Scholar 

  59. A. P. Kriven'ko and T. F. Kotenko, Khim. Geterotsikl. Soedin., No. 12, 1639 (1974).

    Google Scholar 

  60. I. N. Klochkova and M. V. Noritsina, in: New Methods for the Synthesis and Investigation of Organic Compounds [in Russian], Part 2, Izd. Leningr, Gos. Univ., Leningrad (1979), p. 70.

    Google Scholar 

  61. M. V. Noritsina, Candidate's Dissertation, Saratov (1967).

  62. A. P. Kriven'ko, T. G. Nikolaeva, A. A. Espenbetov, Yu. T. Struchkov, and V. G. Kharchenko, Khim. Geterotsikl. Soedin., No. 1, 66 (1985).

    Google Scholar 

  63. I. N. Klochkova, M. V. Noritsina, and O. Yu. Rastegaev, USSR Inventor's Certificate No. 1049482; Byull. Izobret., No. 39, 27 (1983).

  64. M. V. Noritsina, I. N. Klochkova, and T. S. Bykovskaya, Khim. Geterotsikl, Soedin., No. 2, 186 (1976).

    Google Scholar 

  65. V. G. Kharchenko, A. P. Kriven'ko, I. A. Markushina, M. V. Noritsina, T. I. Gubina, G. E. Marinicheva, T. G. Nikolaeva, I. N. Klochkova, and N. V. Shulyakovskaya, in: Catalytic Processes in the Liquid Phase [in Russian], Part 2, Alma-Ata (1978), p. 92.

  66. I. N. Klochkova, M. V. Moritsina, and L. K. Kulikova, Khim.-farm. Zh., No. 9, 63 (1977).

    Google Scholar 

  67. T. G. Nikolaeva and A. P. Kriven'ko, in: The Chemistry and Technology of Furan Compounds [in Russian], Izd. Krasnodarsk. Politekh. Inst., Krasnodar (1982), p. 65.

    Google Scholar 

  68. A. P. Kriven'ko, T. G. Nikolaeva, A. A. Espenbetov, N. T. Komyagin, N. N. Sorokin, Yu. T. Struchkov, and V. G. Kharchenko, Khim. Geterotsikl. Soedin., No. 1, 71 (1985).

    Google Scholar 

  69. V. M. Potapov, Stereochemistry [in Russian], Khimiya, Moscow (1976), p. 344.

    Google Scholar 

  70. M. V. Noritsina (Noritzina) and I. N. Klochkova, in: Collection of Lectures of the 3rd International Symposium on Furan Chemistry, Czechoslovakia (1979), p. 228.

  71. D. Chadwick, ibid., p. 39.

  72. A. I. Brodskii, The Chemistry of Isotopes [in Russian], Izd. Akad. Nauk SSSR, Moscow (1957), p. 287.

    Google Scholar 

  73. I. N. Klochkova, S. A. Lazarev. V. G. Andrianov, Yu. T. Struchkov, G. K. Kravtsova, and M. V. Noritsina, Khim. Geterotsikl. Soedin., No. 2, 222 (1983).

    Google Scholar 

  74. M. V. Noritsina, I. N. Klochkova, and N. N. Sorokin, Khim. Geterotsikl. Soedin., No. 12, 1648 (1984).

    Google Scholar 

  75. I. F. Bel'skii and N. I. Shuikin, Dokl. Akad. Nauk SSSR, 137, 331 (1961).

    Google Scholar 

  76. I. F. Bel'skii, Zh. Obshch, Khim., 32, 2905 (1962).

    Google Scholar 

  77. I. F. Bel'skii, Izv. Akad. Nauk SSSR, Ser. Khim., No. 6, 1077 (1962).

    Google Scholar 

  78. I. F. Bel'skii, N. I. Shuikin, and G. E. Skobtsova, Izv. Akad. Nauk SSSR, Ser. Khim., No. 9, 1678 (1963).

    Google Scholar 

  79. N. I. Shuikin, I. F. Bel'skii, and G. E. Abgaforova, Izv. Akad. Nauk SSSR, Ser. Khim., No. 1, 163 (1965).

    Google Scholar 

  80. G. E. Abgaforova, N. I. Shuikin, and I. F. Bel'skii, Izv. Akad. Nauk SSSR, Ser. Khim., No. 4, 734 (1965).

    Google Scholar 

  81. V. G. Kharchenko, A. P. Kriven'ko, and T. G. Nikolaeva, USSR Inventor's Certificate No. 1030359; Byull. Izobret., No. 27, 106 (1983).

  82. V. G. Kharchenko, A. P. Kriven'ko, and T. G. Nikolaeva, Khim. Geterotsikl. Soedin., No. 11, 1561 (1983).

    Google Scholar 

  83. T. G. Nikolaeva and A. P. Kriven'ko, in: Research on the Synthesis and Catalysis of Organic Compounds [in Russian], Vol. 2, Izd. Saratovsk. Univ., Saratov (1983), p. 68.

    Google Scholar 

  84. T. G. Nikolaeva and A. P. Kriven'ko, in: Advances in the Chemistry of Nitrogen Heterocycles [in Russian], Rostov-on-Don (1983), p. 55.

  85. N. S. Kozlov, L. I. Moiseenok, and S. I. Lozintsev, Dokl. Akad. Nauk SSSR, 252, 1132 (1980).

    Google Scholar 

  86. L. I. Moiseenok, in: Materials from the Conference of Young Scientists of the Chemistry Department of Moscow State University Dedicated to the 26th Session of the Communist Party of the Soviet Union [in Russian], Izd. Mosk. Gos. Univ., Moscow (1981), p. 493.

    Google Scholar 

  87. N. S. Kozlov, L. P. Dmitriev, and M. I. Kozlyak, Izv. Akad. Nauk Belorussk. SSSR, Ser. Khim., 6, 9 (1977).

    Google Scholar 

  88. V. G. Kharchenko and S. N. Chalaya, 1,5-Diketones [in Russian], Izd. Saratovsk. Univ., Satatov (1977), p. 4.

    Google Scholar 

  89. O. V. Fedotova, A. P. Kriven'ko, V. G. Kharchenko, and M. N. Tilichenko, Manuscript Deposited in the All-Union Institute of Scientific and Technical Information, No. 2254-76 Dep.; Ref. Zh. Khim., 3Zh257 (1977).

  90. A. P. Kriven'ko, T. G. Nikoaleva, O. V. Fedotova, and P. V. Reshetov, in: Nucleophilic Reactions of Carbonyl Compounds [in Russian], Izd. Saratovsk. Univ., Saratov (1982), p. 56.

    Google Scholar 

  91. V. G. Kharchenko, A. P. Kriven'ko (Krivenko), O. V. Fedotova, and T. G. Nikolaeva (Nickolaeva), in: The 7th Symposium on the Chemistry of Heterocyclic Compounds, Czechoslovakia (1981), p. 200.

  92. V. G. Kharchenko, A. P. Kriven'ko, T. G. Nikolaeva, and P. V. Reshetov, USSR Inventor's Certificate No. 939442; Byull. Izobret., No. 24, 124 (1982).

  93. V. G. Kharchenko, A. P. Kriven'ko, and T. G. Nikolaeva, USSR Inventor's Certificate No. 1057496; Byull. Izobret., No. 44, 102 (1983).

  94. V. G. Kharchenko, A. P. Kriven'ko, and T. G. Nikolaeva, USSR Inventor's Certificate No. 1010060; Byull. Izobret., No. 13, 158 (1983).

  95. V. G. Kharchenko, N. S. Smirnova, A. P. Kriven'ko, O. V. Fedotova, T. G. Nikolaeva, and L. I. Markova, in: The Chemistry of Dicarbonyl Compounds [in Russian], Izd. Rizhsk. Politekh. Inst., Riga (1981), p. 225.

    Google Scholar 

  96. D. H. Johnson, J. Chem. Soc., C, No. 14, 1284 (1967).

    Google Scholar 

  97. A. P. Kriven'ko, O. V. Fedotova, P. V. Reshetov, and V. G. Kharchenko, Khim. Geterotsikl. Soedin., No. 12, 1652 (1984).

    Google Scholar 

  98. J. Colonge and J. Dreux, Bull. Soc. Chim. Fr., No. 3, 447 (1957).

    Google Scholar 

  99. R. Allwin, J. Colonge, R. Crieger, and J. Dreux, Bull. Soc. Chim. Fr., Nos. 8–9, 1178 (1958).

    Google Scholar 

  100. M. N. Tilichenko and V. I. Vysotskii, Dokl. Akad. Nauk SSSR, 119, 1162 (1958).

    Google Scholar 

  101. M. N. Tilichenko and V. G. Kharchenko, Zh. Obshch. Khim., 29, 2370 (1959).

    Google Scholar 

  102. M. N. Tilichenko and V. G. Kharchenko, Zh. Obshch. Khim., 30, 2283 (1960).

    Google Scholar 

  103. V. Balian, Chem. Rev., 83, 379 (1983).

    Google Scholar 

  104. E. S. Karaulov, A. A. Usol'tsev, and M. N. Tilichenko, Khim. Geterotsikl. Soedin., No. 4, 472 (1976).

    Google Scholar 

  105. V. I. Vysotskii and M. N. Tilichenko, Khim. Geterotsikl. Soedin., No. 3, 383 (1976).

    Google Scholar 

  106. T. V. Moskovkina, M. N. Tilichenko, V. M. Kurikenko, and L. P. Fedyaeva-Basova, Khim.-farm. Zh., No. 3, 3 (1973).

    Google Scholar 

  107. N. Barbulescu and F. Potmischil, Rev. Chim., (RSR), 14, 1427 (1969).

    Google Scholar 

  108. N. Barbulescu and F. Potmischil, Tetrahedron Lett., No. 27, 2309 (1969).

    Google Scholar 

  109. N. Barbulescu and F. Potmischil, Rev. Chim. (RSR), 21, 677 (1970).

    Google Scholar 

  110. N. Barbulescu and F. Potmischil, Rev. Roum. Chim., 15, 1601 (1970).

    Google Scholar 

  111. V. I. Vysotskii and M. N. Tilichenko, Khim. Geterotsikl. Soedin., No. 3, 376 (1971).

    Google Scholar 

  112. L. M. Eremeeva, Yu. V. Vasilenko, V. A. Kaminskii, and M. N. Tilichenko, Khim. Geterotsikl Soedin., No. 10, 1361 (1977).

    Google Scholar 

  113. B. D. Tilak, T. Ravindranathan, and X. N. Subbaswami, Indian J. Chem., 6, 422 (1968).

    Google Scholar 

  114. V. A. Kaminskii, A. N. Saverchenko, and M. N. Tilichenko, Khim. Geterotsikl. Soedin., No. 11, 1539 (1970).

    Google Scholar 

  115. M. N. Tilichenko, V. I. Vysotskii, and V. G. Kharchenko, Uch. Zap. Saratovsk. Gosudarstv. Univ., Ser. Shim., 71, 159 (1959).

    Google Scholar 

  116. V. I. Vysotskii, Zh. Org. Khim., 4, 1494 (1968).

    Google Scholar 

  117. T. V. Moskovkina, V. A. Kaminskii, V. I. Vysotskii, and M. N. Tilichenko, Khim. Geterotsikl. Soedin., No. 6, 826 (1973).

    Google Scholar 

  118. V. I. Vysotskii, Khim. Geterotsikl. Soedin., No. 9, 1236 (1970).

    Google Scholar 

  119. V. I. Alekseev, V. A. Kaminskii, and M. N. Tilichenko, Khim. Geterotsikl. Soedin., No. 7, 957 (1976).

    Google Scholar 

  120. Y. Watanabe, S. Ch. Shim, T. Mitsudo, M. Yamashita, and Y. Takegami, Chem. Lett., No. 9, 995 (1975).

    Google Scholar 

  121. Y. Watanabe, S. Ch. Shim, T. Mitsudo, M. Yamashita, and Y. Takegami, Bull. Chem. Soc. Jpn., 49, 2302 (1976).

    Google Scholar 

  122. R. F. Borch. M. D. Bernstein, and H. D. Durst, J. Am. Chem. Soc., 93, 2897 (1971).

    Google Scholar 

  123. A. S. Kende, T. J. Bentley, R. A. Mader, and D. Ridge, J. Am. Chem. Soc., 96, 4332 (1974).

    Google Scholar 

  124. S. F. Nelson and G. R. Weisman, Tetrahedron Lett., No. 26, 2321 (1973).

    Google Scholar 

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  1. N. G. Chernyshevskii Saratov State University, 410600, Saratov

    A. P. Kriven'ko, T. G. Nikolaeva & V. G. Kharchenko

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  1. A. P. Kriven'ko
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  2. T. G. Nikolaeva
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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 4, pp. 435–448, April, 1987.

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Kriven'ko, A.P., Nikolaeva, T.G. & Kharchenko, V.G. Reductive amination in the synthesis of azaheterocycles (review). Chem Heterocycl Compd 23, 363–375 (1987). https://doi.org/10.1007/BF00546725

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