Skip to main content
SpringerLink
Log in

Catalytic synthesis of nitrogen-containing heterocycles (a review)

  • Published:
Chemistry of Heterocyclic Compounds Aims and scope

Abstract

The process of the catalytic synthesis of a number of nitrogenous heterocyclic compounds based on the utilization of reactions involving the amination of oxygen-containing heterocycles, the dehydration cyclization of amino alcohols, the deamination of di- and polyamines, and the intermolecular dehydration cyclization of glycols with diamines have been 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. A. E. Chichibabin, Zh. Russ. Fiz.-khim. Ova.,47, 703 (1915);54, 411 (1924).

    Google Scholar 

  2. A. E. Chichibabin, P. A. Moshkin, and L. S. Tyazhelova, Zh. Russ. Fiz.-khim. Ova.,54, 413 (1924).

    Google Scholar 

  3. M. I. Farberov, V. V. Antonova, B. F. Ustavshchikov, and N. A. Titova, Khim. Geterotsikl. Soedin., No. 12, 1587 (1975).

    Google Scholar 

  4. I. Ya. Lazdin'sh and A. A. Avots, Khim. Geterotsikl. Soedin., No. 8, 1011 (1979).

    Google Scholar 

  5. A. P. Ivanovskii, V. A. Shikhanov, A. M. Kut'in, and M. A. Korshunov, in: Catalytic Synthesis and Conversions of Heterocyclic Compounds (Heterogeneous Catalysis) [in Russian], Zinatne, Riga (1976), p. 86.

    Google Scholar 

  6. I. Ya. Lazdyn'sh, M. K. Sile, M. V. Shimanskaya, and A. A. Avots, ibid., in:, p. 93.

    Google Scholar 

  7. D. K. Kurgan and M. V. Shimanskaya, in: Piperazine [in Russian], Izd. Akad. Nauk Latv. SSR, Riga (1965), p. 7.

    Google Scholar 

  8. M. V. Shimanskaya, S. A. Giller, and A. Ya. Karmil'chik, Izv. Akad. Nauk Latv. SSR, No. 3, 37 (1976).

    Google Scholar 

  9. Yu. K. Yur'ev, Zh. Obshch. Khim.,6, 972 (1936).

    Google Scholar 

  10. J. K. Yur'ev (Jurjew) and P. M. Rakitin, Chem. Ber.,69, 2492 (1936).

    Google Scholar 

  11. Yu. K. Yur'ev and P. M. Rakitin, Zh. Obshch. Khim.,7, 485 (1937).

    Google Scholar 

  12. Yu. K. Yur'ev and M. D. Prokina, Zh. Obshch. Khim.,7, 1868 (1937).

    Google Scholar 

  13. Yu. K. Yur'ev and G. A. Minkina, Zh. Obshch. Khim.,7, 2945 (1937).

    Google Scholar 

  14. Yu. K. Yur'ev, Kh. M. Minachev, and K. A. Samurskaya, Zh. Obshch. Khim.,9, 1710 (1939).

    Google Scholar 

  15. Yu. K. Yur'ev and V. A. Tronova, Zh. Obshch. Khim.,10, 31 (1940);21, 742 (1951).

    Google Scholar 

  16. Yu. K. Yur'ev and I. S. Levi, Vestn. Mosk. Gos. Univ., Ser. Khim., No. 11(2), 153 (1956).

    Google Scholar 

  17. Yu. K. Yur'ev, in: Aspects of the Use of Pentosan-Containing Raw Materials [in Russian], Izd. Akad. Nauk Latv. SSR, Riga (1958), p. 405.

    Google Scholar 

  18. C. A. Bordner, U.S. Patent No. 2,600,289; Chem. Abstr.,47, 4373 (1953).

    Google Scholar 

  19. W. Reppe, Ann.,596, 143 (1955).

    Google Scholar 

  20. Y. Mori, S. Miyajima, and T. Shirao, Japanese Patent No. 5,242,107 (1972); Ref. Zh. Khim., 19N140P (1977).

  21. L. Meszaros and M. Bartok, Acta Phys. Chem. Szeged.,4, 153 (1958).

    Google Scholar 

  22. R. B. Bishop and W. J. Denton, US Patent No. 2,478,452; Chem. Abstr.,44, 665 (1950).

    Google Scholar 

  23. L. Meszaros and M. Bartok, Acta Phys. Chem. Szeged.,4, 161 (1958).

    Google Scholar 

  24. Kh. M. Vasserman, S. A. Giller, and A. A. Avots, Izv. Akad. Nauk Latv. SSR, No. 5, 79 (1958).

    Google Scholar 

  25. T. Kawaguchi, T. Kita, and H. Naito, Japanese Patent No. 68-19,940; Chem. Abstr.,70, 68133 (1969).

    Google Scholar 

  26. M. Kubo and K. Yasuda, Japanese Patent No. 75-112,362; Chem. Abstr.,84, 53180 (1976).

    Google Scholar 

  27. M. Kubo and K. Yasuda, Japanese Patent No. 75-112,361; Chem. Abstr.,84, 59181 (1976).

    Google Scholar 

  28. Y. Ono, K. Hatada, K. Fujita, A. Holgeri, and T. Keii, J. Catal.,41, 322 (1976).

    Google Scholar 

  29. N. Nomura, T. Tomogawa, and S. Kikkawa, Sekiyu Gakkai Shi,20, 419 (1977); Chem. Abstr.,88, 120895 (1978).

    Google Scholar 

  30. A. A. Avots, I. Ya. Lazdin'sh, M. K. Sile, and V. S. Aizbalts, Izv. Akad. Nauk Latv. SSR, Ser. Khim., No. 3, 333 (1978).

    Google Scholar 

  31. A. A. Avots, I. Ya. Lazdin'sh, M. K. Sile, and V. S. Aizbalts, Izv. Akad. Nauk Latv. SSR, Ser. Khim., No. 3, 333 (1978).

    Google Scholar 

  32. Yu. K. Yur'ev, K. Ya. Novitskii, and É. I. Mingulina, Dokl. Akad. Nauk SSSR,74, 87 (1950).

    Google Scholar 

  33. M. S. Malinovskii and S. N. Baranov, Zh. Prikl. Khim.,25, 410 (1952).

    Google Scholar 

  34. A. A. Avots, I. I. Ioffe, M. K. Sile, and M. V. Shimanskaya, USSR Patent No. 366, 193 (Inventor's Certificate); Byull. Izobr., No. 7, 45 (1973).

  35. M. K. Sile, A. A. Avots, M. V. Shimanskaya, I. I. Ioffe, and G. S. Idlis, USSR Patent No. 230,166 (Inventor's Certificate); Byull. Izobr., No. 34, 31 (1968).

  36. M. K. Sile, A. A. Avots, M. V. Shimanskaya, and G. Yu. Strautyn'sh, Izv. Akad. Nauk Latv. SSR, Ser. Khim., No. 5, 567 (1969).

    Google Scholar 

  37. M. K. Sile, A. A. Avots, M. V. Shimanskaya, and I. I. Ioffe, Izv. Akad. Nauk Lavt. SSR, Ser. Khim., No. 4, 501 (1971).

    Google Scholar 

  38. M. K. Sile, A. A. Avots, M. V. Shimanskaya, and I. I. Ioffe, Izv. Akad. Nauk Latv. SSR, Ser. Khim., No. 1, 54 (1972).

    Google Scholar 

  39. M. K. Sile, A. A. Avots, M. V. Shimanskaya, and I. I. Ioffe, Izv. Akad. Nauk Latv. SSR, Ser. Khim., No. 2, 218 (1972).

    Google Scholar 

  40. Yu. K. Yur'ev and K. Yu. Novitskii, Uch. Zap. Mosk. Gos. Univ.,151, No. 8, 199 (1951).

    Google Scholar 

  41. M. K. Sile, A. A. Avots, I. I. Ioffe, and M. V. Shimanskaya, in: Heterogeneous Catalysis and the Synthesis and Conversion of Heterocyclic Compounds [in Russian], Zinatne, Riga (1971), p. 169.

    Google Scholar 

  42. A. Avots, L. Ozolin'sh, U. Pinka, and M. Sile, Izv. Akad. Nauk Latv. SSR, Ser. Khim., No. 5, 563 (1975).

    Google Scholar 

  43. A. Lattes, A. de Savignac, and J. Carles, Compt. Rend.,253, 2714 (1961).

    Google Scholar 

  44. A. A. Anderson, D. A. Kurgan, S. A. Giller, and M. V. Shimanskaya, in: Piperazine [in Russian], Zinatne, Riga (1965), p. 25.

    Google Scholar 

  45. T. Agawa, Y. Ohki, and K. Hotta, Japanese Patent No. 75-10,593; Chem. Abstr.83, 163983 (1975).

    Google Scholar 

  46. K. M. Akhmerov, D. Yusupov, A. B. Kuchkarov, and K. A. Akhmedov, USSR Patent No. 503,856 (Inventor's Certificate); Byull. Izobr., No. 7, 66 (1976).

  47. K. M. Akhmerov, D. Yusupov, A. B. Kuchkarov, and K. Akhmedov, Khim. Geterotsikl. Soedin., No. 3, 428 (1974).

    Google Scholar 

  48. J. Semb and J. R. Vaughan, British Patent No. 833,589; Chem. Abstr.,54, 22691 (1960).

    Google Scholar 

  49. G. F. Tereshchenko, V. K. Krotova, T. A. Mikhailova, N. L. Yushina, and V. G. Golyaev, USSR Patent No. 545,633 (Inventor's Certificate); Ref. Zh. Khim., 20N56P (1977).

  50. L. A. Hamilton and P. S. Landis, US Patent No. 3,369,019; Ref. Zh. Khim., 16N244P (1969).

  51. A. A. Balandin, V. A. Ferapontov, E. I. Karpeiskaya, L. S. Gorshkova, and A. A. Tolstopyatova, Dokl. Akad. Nauk SSSR,168, 1061 (1966).

    Google Scholar 

  52. N. B. Godfrey, US Patent No. 3,120,524; Chem. Abstr.,60, 9293 (1964).

    Google Scholar 

  53. T. Ishiguro, E. Kilamura, and M. Matsumura, J. Pharm. Soc. Jpn.,74, 1162 (1954); Chem. Abstr.,49, 14767 (1955).

    Google Scholar 

  54. T. Sasaki, Yuki Gosei Kagaku Kyokai Shi,17, 17 (1959); Chem. Abstr.,53, 7191 (1959).

    Google Scholar 

  55. M. W. Long, US Patent No. 2,910,477; Chem. Abstr.,54, 5713 (1960).

    Google Scholar 

  56. F. Matsuda, T. Takahashi, Y. Koyama, and Y. Hirona, Japanese Patent No. 75,140,466; Chem. Abstr.,85, 46699 (1976).

    Google Scholar 

  57. W. H. Brader and T. H. Cour, US Patent No. 3,231,573; Chem. Abstr.,64, 9746 (1966).

    Google Scholar 

  58. K. M. Akhmerov, D. Yusupov, A. B. Kuchkarov, and K. Akhmedov, USSR Patent No. 514,820 (Inventor's Certificate); Byull. Izobr., No. 19, 54 (1976).

  59. W. H. Brader and R. L. Rowton, US Patent No. 3,172,891; Chem. Abstr.,63, 2987 (1965).

    Google Scholar 

  60. E. L. Yeakey, J. Templeton, West German Patent No. 2,401,095; Chem. Abstr.,81, 152247 (1974).

    Google Scholar 

  61. H. P. Pfann, US Patent No. 2,427,473; Chem. Abstr.,42, 623 (1948).

    Google Scholar 

  62. Chas Pfizer and Co., British Patent No. 816,037; Chem. Abstr.,54, 16470 (1960).

    Google Scholar 

  63. Y. Ohashi, H. Aso, and F. Ito, Japanese Patent No. 74-125,375; Chem. Abstr.,83, 10145 (1975).

    Google Scholar 

  64. H. Bosche, K. Baer, and K. Schneider, West German Patent No. 2,442,929; Ref. Zh. Khim., 2N212 (1977).

  65. W. H. Brader, US Patent No. 3,157,657; Chem. Abstr.,62, 4038 (1965).

    Google Scholar 

  66. Chemische Werke Huels A. G., French Patent No. 1,377,949; Chem. Abstr.,62, 7779 (1965).

    Google Scholar 

  67. R. L. Mascioli, US Patent No. 3,166,558; Chem. Abstr.,62, 13160 (1965).

    Google Scholar 

  68. M. Kawamura, S. Akutsu, and M. Madaeda, Japanese Patent No. 74-11,712; Chem. Abstr.,81, 77965 (1974).

    Google Scholar 

  69. H. Dörries, West German Patent No. 1,085,161; Chem. Abstr.,55, 16576 (1961).

    Google Scholar 

  70. T. Ishiguro, E. Kitamura, and M. Matsumura, Yakugaku Zasshi,78, 150 (1959); Chem. Abstr.,53, 13163 (1959).

    Google Scholar 

  71. Wyandotte Chemicals Corp., British Patent No. 781,701; Chem. Abstr.,52, 2099 (1958).

    Google Scholar 

  72. Wyandotte Chemicals Corp., British Patent No. 791,050; Chem. Abstr.,52, 15599 (1958).

    Google Scholar 

  73. W. K. Langdon, U. S. Patent No. 2,813,869; Chem. Abstr.,52, 5489 (1958).

    Google Scholar 

  74. W. K. Langdon, West German Patent No. 1,171,925; Chem. Abstr.,61, 8322 (1964).

    Google Scholar 

  75. W. W. Lewis and W. K. Langdon, British Patent No. 836,289; Chem. Abstr.,56, 3489 (1962).

    Google Scholar 

  76. T. Sasaki, Yuki Gosei Kagaku Kyokai Shi,16, 614 (1958); Chem. Abstr.,53, 3234 (1959).

    Google Scholar 

  77. Dow Chemical Co., British Patent No. 814,331; Chem. Abstr.,54, 594 (1960).

    Google Scholar 

  78. G. W. Fowler, US Patent No. 2,980,682; Chem. Abstr.,55, 17665 (1961).

    Google Scholar 

  79. W. K. Langdon, W. W. Lewis, D. R. Jackson, M. Cenker, and G. E. Baxter, Ind. Eng. Chem. Prod. Res. Dev.,3, No. 1, 8 (1964).

    Google Scholar 

  80. W. H. Brader and R. L. Rowton, French Patent No. 1,381,243; Chem. Abstr.,62, 14698 (1965).

    Google Scholar 

  81. T. Ishiguro and M. Matsumura, Yakugaku Zasshi,79, 302 (1959); Chem. Abstr.,53, 16147 (1959).

    Google Scholar 

  82. W. K. Langdon, West German Patent No. 1,181,225; Chem. Abstr.,62, 5286 (1965).

    Google Scholar 

  83. W. P. Coker and G. W. Strother, US Patent No. 2,861,994; Chem. Abstr.,53, 12319 (1959).

    Google Scholar 

  84. Yu. K. Yur'ev, G. P. Mikhailovskii, and S. Z. Shapiro, Zh. Obshch. Khim.,19, 2217 (1949).

    Google Scholar 

  85. E. Lorz and R. S. Bagby, US Patent No. 3,056,797; Chem. Abstr.,59, 1661 (1963).

    Google Scholar 

  86. V. I. Karzhev, M. G. Severyanova, and A. N. Siova, Khim. Tverd. Topliva,7, 282, 559 (1936).

    Google Scholar 

  87. B. L. Moldavskii and G. D. Kamusher, Dokl. Akad. Nauk SSSR,1, 341 (1936).

    Google Scholar 

  88. B. A. Kazanskii and A. F. Plate, Chem. Ber.,69, 1862 (1936).

    Google Scholar 

  89. M. I. Rozengart and B. A. Kazanskii, Usp. Khim.,40, 1538 (1971).

    Google Scholar 

  90. B. A. Kazanskii (Kazansky), G. V. Isagulyants, M. J. Rozengart, Yu. G. Dubinskii (Dubinsky), and L. J. Kovalenko, Catalysis, Vol. 2, N.H.P.C., Amsterdam-London (1973), ref. 92, p. 1277.

    Google Scholar 

  91. M. I. Yakushkin and V. I. Kotov, in: Heterogeneous Catalysis in the Synthesis and Conversions of Heterocyclic Compounds [in Russian], Zinatne, Riga (1972), p. 17.

    Google Scholar 

  92. A. L. Liberman, O. V. Bragin, and B. A. Kazanskii, Izv. Akad. Nauk SSSR, Otd. Khim., Nauk, No. 3, 525 (1961).

    Google Scholar 

  93. O. V. Bragin, G. K. Gur'yanova, and A. L. Liberman, Izv. Akad. Nauk SSSR, Ser. Khim., No. 7, 1242 (1965).

    Google Scholar 

  94. O. V. Bragin and A. L. Liberman, in: Heterogeneous Catalysis in the Synthesis and Conversions of Heterocyclic Compounds [in Russian], Zinatne, Riga (1971), p. 117.

    Google Scholar 

  95. G. Ya. Kondrat'eva, Yu. S. Dol'skaya, and B. A. Kazanskii, in: Catalytic Synthesis and Conversions of Heterocyclic Compounds (Heterogeneous Catalysis) [in Russian], Zinatne, Riga (1976), p. 53.

    Google Scholar 

  96. G. Ya. Kondrat'eva, Yu. S. Dol'skaya, E. A. Aleksandrova, and B. A. Kazanskii, Khim. Geterotsikl. Soedin., No. 7, 970 (1972).

    Google Scholar 

  97. B. A. Kazanskii, Investigations in the Field of Organic Catalysis [in Russian], Nauka, Moscow (1977), p. 283.

    Google Scholar 

  98. G. S. Bond, Catalysis by Metals, Academic Press, New York (1962).

    Google Scholar 

  99. K. Hayano, H. Yoneyama, Y. Hayashi, and Y. Noda, Tanabe Seiyaku Kenkyu, Nempo,3, 32 (1958);52, 20188 (1958).

    Google Scholar 

  100. W. R. Miller, US Patent No. 2,809,195; Chem. Abstr.,52, 1286 (1958).

    Google Scholar 

  101. W. R. Miller, US Patent No. 2,809,196; Chem. Abstr.,52, 1286 (1958).

    Google Scholar 

  102. Dow Chemical Co., British Patent No. 809,239; Chem. Abstr.,54, 594 (1960).

    Google Scholar 

  103. G. F. McKenzie and K. L. Turbin, US Patent No. 2,901,482; Chem. Abstr.,54, 9961 (1960).

    Google Scholar 

  104. S. A. Giller, M. V. Shimanskaya, A. A. Lazdyn'sh, D. K. Kurgan, B. É. Gofman, and A. A. Anderson, in: Ninth Mendeleev Congress on General and Applied Chemistry, Abstracts of Reports, No. 5, Chemistry and Technology of Drugs Section [in Russian], Moscow (1965), p. 166.

  105. D. K. Kurgan, A. A. Lazdyn'sh, and M. V. Shimanskaya, in: Piperazine [in Russian], Zinatne, Riga (1965), p. 55.

    Google Scholar 

  106. M. V. Shimanskaya, B. É. Gofman, A. A. Lazdyn'sh, and S. A. Giller, in: Heterogeneous Catalysis in the Synthesis and Conversion of Heterocyclic Compounds [in Russian], Zinatne, Riga (1971), p. 185.

    Google Scholar 

  107. S. A. Giller, M. V. Shimanskaya, B. E. Gofman, and A. A. Lazdyn'sh, USSR Patent No. 271,525 (Inventor's Certificate); Byull. Izobr., No. 18, 26 (1970).

  108. S. A. Giller, M. V. Shimanskaya, B. É. Gofman, and A. A. Lazdyn'sh, USSR Patent No. 311,915 (Inventor's Certificate); Byull. Izobr., No. 25, 99 (1971).

  109. M. Shimanskaya, A. Ermakova, E. Stefoglo, B. Gofman, V. Garde, A. Avots, A. Lazdyn'sh, and D. Fel'dman, in: Chemical Reactors-5 [in Russian], Ufa (1974), p. 138.

  110. H. Graefje and H. H. Stechl, West German Patent No. 2,230,735; Chem. Abstr.,80, 83063 (1974).

    Google Scholar 

  111. T. A. Mikhailova, D. Z. Zavel'skii, V. K. Krotova, T. I. Orlova, S. S. Shcherbakova, and A. M. Grachev, USSR Patent No. 427,936 (Inventor's Certificate); Byull. Izobr., No. 18, 58 (1974).

  112. S. A. Giller, M. V. Shimanskaya, B. É. Gofman, D. P. Fel'dman, Ya. V. Ziemelis, A. A. Lazdyn'sh, V. Ya. Sile, and A. A. Avots, in: Second All-Union Conference on the Kinetics of Catalytic Reactions [in Russian], Vol. 2, Novosibirsk (1975), p. 72.

  113. S. A. Giller, M. V. Shimanskaya, B. É. Gofman, A. A. Lazdyn'sh, and Ya. V. Ziemelis, USSR Patent No. 467,076; Byull. Izobr., No. 14, 44 (1975).

  114. D. P. Fel'dman, B. E. Gofman, Ya. V. Ziemelis, D. Ya. Kozlovskaya, and M. V. Shimanskaya, paper deposited at VINITI, No. 731-77; Kinet. Katal.,18, No. 6, 1612 (1977).

  115. H. Pfann and J. Dixon, US Patent No. 2,455,504; Chem. Abstr.,43, 2242 (1949).

    Google Scholar 

  116. T. Ishiguro, E. Kitamura, M. Matsumura, and H. Ogawa, J. Pharm. Soc. Japan,75, 1370 (1955); Chem. Abstr.,50, 10106 (1956).

    Google Scholar 

  117. A. Campbell, US Patent No. 2,873,274; Chem. Abstr.,53, 18971 (1959).

    Google Scholar 

  118. E. C. Herrick, US Patent No. 2,937,176; Chem. Abstr.,54, 21145 (1960).

    Google Scholar 

  119. J. H. Krause, US Patent No. 2,985,658; Chem. Abstr.,57, 9864 (1962).

    Google Scholar 

  120. J. H. Krause, R. K. Smith, and E. C. Herrick, British Patent No. 871,754; Chem. Abstr.,56, 3492 (1962).

    Google Scholar 

  121. W. E. Erner, US Patent No. 3,029,240; Chem. Abstr.,57, 12513 (1962).

    Google Scholar 

  122. W. H. Brader, US Patent No. 3,056,788; Chem. Abstr.,59, 1661 (1963).

    Google Scholar 

  123. W. H. Brader, US Patent No. 3,120,526; Chem. Abstr.,60, 11895 (1964).

    Google Scholar 

  124. R. W. Swanson, US Patent No. 3,146,236; Chem. Abstr.,61, 13330 (1964).

    Google Scholar 

  125. R. W. Swanson, US Patent No. 3,148,190; Chem. Abstr.,62, 1674 (1965).

    Google Scholar 

  126. S. A. Giller, M. V. Shimanskaya, B. É. Gofman, and A. A. Anderson, in: Piperazine [in Russian], Zinatne, Riga (1965), p. 41.

    Google Scholar 

  127. A. A. Anderson, S. P. Yurel', M. V. Shimanskaya, and S. A. Giller, Dokl. Akad. Nauk SSSR,169, 1332 (1966).

    Google Scholar 

  128. A. A. Anderson, S. P. Yurel', and M. V. Shimanskaya, Khim. Geterotsikl. Soedin., No. 2, 346 (1967).

    Google Scholar 

  129. A. A. Anderson, S. P. Yurel', and M. V. Shimanskaya, Izv. Akad. Nauk Latv. SSR, Ser. Khim., No. 6, 683 (1968).

    Google Scholar 

  130. A. A. Anderson, S. P. Yurel', and M. V. Shimanskaya, Izv. Akad. Nauk Latv. SSR, Ser. Khim., No. 1, 47 (1971).

    Google Scholar 

  131. A. A. Anderson, S. P. Yurel', and M. V. Shimanskaya, in: Heterogeneous Catalysis in the Synthesis and Conversion of Heterocyclic Compounds [in Russian], Zinatne, Riga (1971), p. 175.

    Google Scholar 

  132. S. P. Yurel', A. A. Anderson, U. A. Pinka, and M. V. Shimanskaya, Izv. Akad. Nauk Latv. SSR, Ser. Khim., No. 6, 691 (1974).

    Google Scholar 

  133. S. P. Yurel', A. A. Anderson, and M. V. Shimanskaya, Izv. Akad. Nauk Latv. SSR, Ser. Khim., No. 6, 729 (1974).

    Google Scholar 

  134. A. A. Anderson, S. P. Yurel', and M. V. Shimanskaya, in: Catalytic Synthesis and Conversion of Heterocyclic Compounds (Heterogeneous Catalysis) [in Russian], Zinatne, Riga (1976), p. 108.

    Google Scholar 

  135. R. Murakami, S. Kato, and H. Mitarashi, West German Patent No. 2,434,913; Chem. Abstr.,82, 156378 (1975).

    Google Scholar 

  136. L. D. Brake, US Patent No. 3,830,800; Chem. Abstr.,81, 169446 (1974).

    Google Scholar 

  137. A. A. Artem'ev, A. S. Slavnova, V. P. Trofilkina, and V. G. Monakova, Proceedings of the State Scientific-Research and Planning Institute of the Nitrogen Industry and Products of Organic Synthesis [in Russian], No. 27 (1975), p. 60; Ref. Zh. Khim., 16B1235 (1975).

    Google Scholar 

  138. J. Okada, S. Morita, and M. Tsuchiya, Yakugaku Zasshi,96, No. 6, 801 (1976); Chem. Abstr.,85, 142251 (1976).

    Google Scholar 

  139. Ya. F. Oshis, A. A. Anderson, and M. V. Shimanskaya, Khim. Geterotsikl. Soedin., No. 6, 967 (1982).

    Google Scholar 

  140. S. A. Giller, M. V. Shimanskaya, B. É. Gofman, and Ya. V. Ziemelis, in: Catalytic Synthesis and Conversions of Heterocyclic Compounds (Heterogeneous Catalysis) [in Russian], Zinatne, Riga (1976), p. 194.

    Google Scholar 

  141. Yu. K. Yur'ev, and N. G. Medovshchikov, Zh. Obshch. Khim.,9, 628 (1939).

    Google Scholar 

  142. T. Sasaki, Yuki Gosei Kagaku Kyokai Shi,16, 461 (1958); Chem. Abstr.,52, 20188 (1958).

    Google Scholar 

  143. A. Farkas and J. H. Kruse, US Patent No. 2,977,363; Chem. Abstr.,55, 17664 (1961).

    Google Scholar 

  144. P. H. Moss, US Patent No. 3,068,232; Chem. Abstr.,58, 12580 (1963).

    Google Scholar 

  145. W. C. Bedoit, US Patent No. 3,155,657; Chem. Abstr.,62, 1669 (1965).

    Google Scholar 

  146. J. T. Patton, W. W. Lewis, and W. K. Langdon, US Patent No. 3,067,202; Chem. Abstr.,58, 10216 (1963).

    Google Scholar 

  147. Kh. I. Areshidze and G. O. Chivadze, Khim. Geterotsikl., No. 7, 937 (1973).

    Google Scholar 

  148. J. Okada and K. Hayakawa, Yakugaku Zasshi,96, 783 (1976); Chem. Abstr.,85, 160027 (1976).

    Google Scholar 

  149. J. Okada, K. Hayakawa, and K. Nakamura, Yakugaku Zasshi,98, 47 (1978); Chem. Abstr.,88, 190746 (1978).

    Google Scholar 

  150. K. Hayakawa and J. Okada, Yakugaku Zasshi,97, 1299 (1977); Chem. Abstr.,89, 24267 (1978).

    Google Scholar 

  151. D. C. Best, West German Patent No. 2,700,339; Chem. Abstr.,87, 151693 (1977).

    Google Scholar 

  152. J. K. Dixon, US Patent No. 2,400,398; Chem. Abstr.,40, 4748 (1946).

    Google Scholar 

  153. J. H. Boothe, British Patent No. 609,924; Chem. Abstr.,43, 1813 (1949).

    Google Scholar 

  154. J. K. Dixon, US Patent No. 2,474,781; Chem. Abstr.,44, 3039 (1950).

    Google Scholar 

  155. J. K. Dixon, US Patent No. 2,474,782; Chem. Abstr.,44, 3039 (1950).

    Google Scholar 

  156. J. K. Dixon, US Patent No. 2,580,211; Chem. Abstr.,46, 6673 (1952).

    Google Scholar 

  157. J. K. Dixon, French Patent No. 54686; Chem. Abstr.,46, 6673 (1952).

    Google Scholar 

  158. Ya. F. Oshis, A. A. Anderson, and M. V. Shimanskaya, USSR Patent No. 891,658 (Inventor' Certificate); Byull. Izobr., No. 47, 106 (1981).

  159. T. Ishiguro, M. Matsumura, and H. Murai, Yakugaku Zasshi,80, 314 (1960);54, 18531 (1960).

    Google Scholar 

  160. S. D. Tarailo, US Patent No. 2,945,858; Chem. Abstr.,55, 1668 (1961).

    Google Scholar 

  161. M. Cenker and G. E. Baxter, US Patent No. 3,005,820; Chem. Abstr.,56, 7335 (1962).

    Google Scholar 

  162. M. Cenker, D. R. Jackson, W. K. Langdon, and W. W. Lewis, Ind. Eng. Chem., Prod. Res. Dev.,3, No. 1, 11 (1964); Chem. Abstr.,60, 8027 (1964).

    Google Scholar 

  163. S. Kajiyama and H. Oba, Japanese Patent No. 74-30,383; Chem. Abstr.,81, 105568 (1974).

    Google Scholar 

  164. S. P. Yurel', A. A. Anderson, and M. V. Shimanskaya, Khim. Geterotsikl. Soedin., No. 10, 1414 (1974).

    Google Scholar 

  165. A. A. Anderson, S. P. Yurel', and M. V. Shimanskaya, USSR Patent No. 523,898 (Inventorjs Certificate); Byull. Izobr., No. 29, 66 (1976).

  166. M. Inoue, S. Enomoto, and J. Imamura, Yakugaku Zasshi,95, 849 (1975); Chem. Abstr.,83, 146830.(1975).

    Google Scholar 

  167. K. Sato, Japanese Patent No. 76-56,479; Chem. Abstr.,86, 29872 (1977).

    Google Scholar 

  168. G. Enomoto, K. Nakayama, T. Aklyama, and Y. Ueno, Japanese Patent No. 77-136,182; Chem. Abstr.,138, 105412 (1978).

    Google Scholar 

  169. A. C. Thomas and C. A. Wellington, J. Chem. Soc., A, No. 19, 2895 (1969).

    Google Scholar 

  170. K. M. Akhmerov, A. B. Kuchkarov, K. Akhmedov, and D. Yusupov, Khim. Geterotsikl. Soedin., No. 2, 277 (1975).

    Google Scholar 

  171. O. V. Krylov, Catalysis by Nonmetals. Rules for the Selection of Catalysts [in Russian], Khimiya, Leningrad (1967).

    Google Scholar 

  172. G. W. A. Fowles and D. K. Jenkins, Inorg. Chem.,3, 257 (1964).

    Google Scholar 

  173. E. I. Karpeiskaya and L. S. Gorshkova, Izv. Akad. Nauk SSSR, Ser. Khim., No. 12, 2716 (1970).

    Google Scholar 

  174. R. N. Keller and L. J. Edwards, J. Am. Chem. Soc.,74, 215 (1952).

    Google Scholar 

  175. W. C. Drinkard, F. H. Bauer, and J. C. Barbar, J. Amer. Chem. Soc.,82, 2992 (1960).

    Google Scholar 

  176. E. Mario and S. M. Bolton, Anal. Chem.,37, 165 (1965).

    Google Scholar 

  177. B. D. Sarma, G. J. Tennenhouse, and J. C. Bailar, J. Am. Soc.,90, 1362 (1968).

    Google Scholar 

  178. B. D. Sarma and J. C. Bailar, J. Am. Chem. Soc.,91, 5958 (1969).

    Google Scholar 

  179. Yu. N. Kukushkin, E. I. Karpeiskaya, and V. A. Trofimov, Zh. Prikl. Khim.,44, 662 (1971).

    Google Scholar 

  180. E. I. Karpeiskaya, Yu. N. Kukushkin, V. A. Trofimov, and I. P. Yakovlev, Zh. Neorg. Khim.,16, 1960 (1971).

    Google Scholar 

  181. E. I. Karpeiskaya, Yu. N. Kukushkin, V. A. Trofimov, and I. P. Yakovlev, Zh. Neorg. Khim.,17, 2189 (1972).

    Google Scholar 

  182. E. I. Karpeiskaya, Yu. N. Kukushkin, V. A. Trofimov, I. P. Yakovlev, and R. A. Vlasova, Zh. Neorg. Khim.,17, 2695 (1972).

    Google Scholar 

  183. E. I. Karpeiskaya, Yu. N. Kukushkin, V. A. Trofimov, I. D. Ratner, and D. P. Shashkin, Izv. Akad. Nauk SSSR, Ser. Khim., No. 2, 338 (1974).

    Google Scholar 

  184. E. I. Karpeiskaya and I. P. Yakovlev, Izv. Akad. Nauk SSSR, Ser. Khim., No. 2, 344 (1974).

    Google Scholar 

  185. D. P. Feld'man, B. É. Gofman, and M. V. Shimanskaya, Izv. Akad. Nauk Latv. SSR, Ser. Khim., No. 6, 739 (1975).

    Google Scholar 

  186. Ya. F. Oshis, A. A. Anderson, and M. V. Shimanskaya, in: Seventh All-Union Seminar on the Application of Optical Spectroscopy in Catalysis. Abstracts of Reports [in Russian], Moscow (1982), p. 49.

  187. Ya. F. Oshis, Dissertation for the Degree of Candidate of Chemical Sciences, Riga (1983).

Download references

Author information

Authors and Affiliations

  1. Institute of Organic Synthesis, Academy of Sciences of the Latvian SSR, 226006

    M. V. Shimanskaya, Ya. F. Oshis & A. A. Anderson

Authors
  1. M. V. Shimanskaya
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Ya. F. Oshis
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. A. A. Anderson
    View author publications

    You can also search for this author in PubMed Google Scholar

Additional information

Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 12, 1587–1601, December, 1983.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Shimanskaya, M.V., Oshis, Y.F. & Anderson, A.A. Catalytic synthesis of nitrogen-containing heterocycles (a review). Chem Heterocycl Compd 19, 1249–1262 (1983). https://doi.org/10.1007/BF00842824

Download citation

  • Received:

  • Revised:

  • Issue Date:

  • DOI: https://doi.org/10.1007/BF00842824

Keywords

Search

Navigation