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Nitroazines. Methods of synthesis (review)

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Chemistry of Heterocyclic Compounds Aims and scope

Abstract

Published data on methods for the production of six-membered nitrogen heterocycles containing a nitrogroup are classified systematically.

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Literature cited

  1. Zh. I. Aksel'rod and V. M. Berezovskii, Usp. Khim., 39, 1337 (1970).

    Google Scholar 

  2. J. H. Ridd, Z. Chem., 8, 201 (1968).

    Google Scholar 

  3. K. Schofield, Quart. Rev., 4, 382 (1950).

    Google Scholar 

  4. S. Rajappa and M. D. Nair, Adv. Heterocycl. Chem., 25, 113 (1979).

    Google Scholar 

  5. D. J. Brown, in: The Pyrimidines, Wiley, New York-London-Sydney (1962).

    Google Scholar 

  6. M. Tišler and B. Stanovnik, Adv. Heterocycl. Chem., 9, 211 (1968).

    Google Scholar 

  7. M. Tišler and B. Stanovnik, Adv. Heterocycl. Chem., 24, 363 (1978).

    Google Scholar 

  8. L. Novacek, K. Palat, and M. Celadnik, Chem. Listy, 57, 299 (1963).

    Google Scholar 

  9. H. J. Den Hertog and J. Overhoff, Rec. Trav. Chim., 49, 552 (1930).

    Google Scholar 

  10. C. D. Johnson, A. R. Katritzky, and M. Viney, J. Chem. Soc., B, No. 11, 1211 (1967).

    Google Scholar 

  11. M. M. Boudakian, U.S. Patent No. 4310671; Ref. Zh. Khim., 21N128 (1982).

  12. A. R. Katritzky, H. O. Tarhan, and S. Tarhan, J. Chem. Soc., B, No. 1, 114 (1970).

    Google Scholar 

  13. A. G. Burton, P. J. Halls, and A. R. Katritzky, J. Chem. Soc., Perkin Trans. II, No. 13, (1972).

  14. A. G. Burton, R. D. Frampton. C. D. Johnson, and A. R. Katritzky, J. Chem. Soc., Perkins Trans. II, No. 13, 1940 (1972).

    Google Scholar 

  15. G. Bianchi, A. G. Burton, C. D. Johnson, and A. R. Katritzky, J. Chem. Soc., Perkin Trans. II, No. 13, 1950 (1972).

    Google Scholar 

  16. A. R. Katritzky and B. J. Ridgewell, J. Chem. Soc., No. 7, 3753 (1963).

    Google Scholar 

  17. Y. Morisava, M. Kataoka, N. Kitano, and T. Matsuzawa, Patent No. 2536202 (BRD); Chem. Abs., 85, 5507 (1976).

    Google Scholar 

  18. E. Plazek, Berichte, 72, 577 (1939).

    Google Scholar 

  19. E. V. Brown and R. H. Neil, J. Org. Chem., 26, 3546 (1961).

    Google Scholar 

  20. L. Achremowicz, T. Batkowski, and Z. Skrowaczewska, Roczn. Chem., 38, 1317 (1964).

    Google Scholar 

  21. L. N. Pino and W. S. Zehrung, J. Am. Chem. Soc., 77, 3154 (1955).

    Google Scholar 

  22. A. Thomas, P. Tomasnik, and G. Herman-Matusiak, Bull. Acad. Pol. Sci., Ser. Sci. Chim., 23, 311 (1975).

    Google Scholar 

  23. H. Kokosinska, A. Thomas, P. Tomasik, and R. Zalewski, Bull. Acad. Pol. Sci., Ser. Sci. Chim., 24, 535 (1976).

    Google Scholar 

  24. L. W. Deady, M. R. Grimmot, and C. H. Potts, Tetrahedron, 35, 2895 (1979).

    Google Scholar 

  25. E. Plazek, A. Marcinikow, and Ch. Stammer, Roczn. Chem., 15 365 (1935); Chem. Abs., 30 1377 (1936).

    Google Scholar 

  26. G. P. Sharnin. I. F. Falyakhov, and F. G. Khairutdinov, Khim. Geterotsikl. Soedin., No. 3, 363 (1980).

    Google Scholar 

  27. G. P. Sharnin, I. F. Falyakhov, and F. G. Khairutdinov, Khim. Geterotsikl. Soedin., No. 12, 1632 (1980).

    Google Scholar 

  28. A. G. Burton, R. D. Frampton, C. D. Johnson, and A. R. Katritzky, J. Chem. Soc., Perkin Trans. II, No. 13, 1943 (1972).

    Google Scholar 

  29. E. Haack, German Patent No. 568549; Chem. Abs., 27, 2697 (1933).

    Google Scholar 

  30. C. Räth, Annalen, 484, 52 (1930).

    Google Scholar 

  31. A. H. Berrie, G. T. Newbold, and F. S. Spring, J. Chem. Soc., No. 10, 2590 (1951).

    Google Scholar 

  32. J. Kozlowska and E. Plazek, Roczn. Chem., 33, 831 (1959).

    Google Scholar 

  33. C. A. Salemink and G. M. can der Want, Rec. Trav. Chim., 68, 1013 (1949).

    Google Scholar 

  34. M. D. Coburn, J. Heterocycl. Chem., 11, 1099 (1974).

    Google Scholar 

  35. R. C. De Selms, J. Org. Chem., 33, 478 (1968).

    Google Scholar 

  36. L. D. Smirnov, R. E. Lokhov, V. P. Lezina, B. E. Zaitsev, and K. M. Dyumaev, Izv. Akad. Nauk SSSR, Ser. Khim., No. 7, 1567 (1969).

    Google Scholar 

  37. K. M. Dyumaev and L. D. Smirnov, Usp. Khim., 44, 1788 (1975).

    Google Scholar 

  38. J. Bernstein, B. Stearns, E. Shaw, and W. A. Lott, J. Am. Chem. Soc., 69, 1151 (1947).

    Google Scholar 

  39. H. J. Den Hertog, C. Jouwersma, A. A. van der Wal, and E. C. C. Willebrands-Schogt, Rec. Trav. Chim., 68, 275 (1949).

    Google Scholar 

  40. E. Koenigs, H. C. Gerdes, and A. Sirot, Berichte, 61, 1022 (1928).

    Google Scholar 

  41. E. Koenigs and A. Fulde, Berichte, 60, 2106 (1927).

    Google Scholar 

  42. W. Gzuba and E. Plazek, Rec. Trav. Chim., 77, 92 (1958).

    Google Scholar 

  43. K. V. Rao and P. Venkateswarlu, J. Heterocycl. Chem., 12, 731 (1975).

    Google Scholar 

  44. F. Kögl, G. M. van der Want, and C. A. Salemink, Rec. Trav. Chim., 67, 29 (1948).

    Google Scholar 

  45. L. N. Yakhontov, M. Ya. Uritskaya, V. A. Loginova, and M. V. Rubtsov, Khim. Geterotsikl. Soedin., No. 3, 456 (1969).

    Google Scholar 

  46. L. D. Smirnov and K. M. Dyumaev, Khim. Geterotsikl. Soedin., No. 9, 1155 (1976).

    Google Scholar 

  47. W. H. Crowe, J. Chem. Soc., No. 9, 2028 (1925).

    Google Scholar 

  48. S. Kruger and F. G. Maun, J. Chem. Soc., No. 8, 2755 (1955).

    Google Scholar 

  49. S. Caldwell and C. E. Martin, J. Heterocycl. Chem., 17, 989 (1980).

    Google Scholar 

  50. R. F. Evans and W. Kynaston, J. Chem. Soc., No. 12, 5556 (1961).

    Google Scholar 

  51. R. B. Brown, J. Am. Chem. Soc., 79, 3565 (1957).

    Google Scholar 

  52. G. C. Wright, U.S. Patent No. 4216327; Ref. Zh. Khim., 50107 (1981).

  53. H. J. den Hertog, M. van Ammers, and S. Schukking, Rec. Trav. Chim., 74, 1171 (1955).

    Google Scholar 

  54. H. J. Den Hertog, C. H. Henkens, and K. Dilz, Rec. Trav. Chim., 72, 296 (1953).

    Google Scholar 

  55. C. D. Johnson, A. R. Katritzky, N. Shakir, and M. J. Viney, J. Chem. Soc., B, No. 11, 1213 (1967).

    Google Scholar 

  56. G. P. Bean, P. J. Brignell, C. D. Johnson, A. R. Katritzky, B. J. Ridgewell, H. O. Tarhan, and A. M. White, J. Chem. Soc., B, No. 11, 1222 (1967).

    Google Scholar 

  57. W. A. Lott and E. Shaw, J. Am. Chem. Soc., 71, 70 (1949).

    Google Scholar 

  58. H. J. Den Hertog and M. van Ammers, Rec. Trav. Chim., 74, 1160 (1955).

    Google Scholar 

  59. M. Van Ammers and H. J. Den Hertog, Rec. Trav. Chim., 75, 1259 (1956).

    Google Scholar 

  60. R. Lewicka and E. Plazek, Rec. Trav. Chim., 78, 644 (1959).

    Google Scholar 

  61. M. J. S. Dewar and P. M. Maitlis, J. Chem. Soc., No. 6, 2521 (1957).

    Google Scholar 

  62. D. H. G. Grant, J. R. Penton, and K. Schofield, J. Chem. Soc., ulB, No. 6 1254 (1971).

    Google Scholar 

  63. K. M. Dyumaev, E. P. Popova, I. F. Mikhailov, A. I. Shibaeva, and L. D. Smirnov, Khim. Geterotsikl. Soedin., No. 6, 805 (1974).

    Google Scholar 

  64. K. Schofield and T. Swuin, J. Chem. Soc., No. 5, 1367 (1949).

    Google Scholar 

  65. B. B. Moodie, J. R. Penton, and K. Schofield, J. Chem. Soc., ulB, No. 7, 1493 (1971).

    Google Scholar 

  66. M. J. S. Dewar and P. M. Maitlis, J. Chem. Soc., No. 3, 944 (1957).

    Google Scholar 

  67. M. Ikehara and G. Shimizu, Chem. Pharm. Bull., 7, 501 (1959).

    Google Scholar 

  68. H. E. Foster and J. Hurst, J. Chem. Soc., Perkin Trans I, No. 23, 2901 (1973).

    Google Scholar 

  69. Yu. M. Yutilov and I. A. Svertilova, Khim. Geterotsikl. Soedin., No. 5, 705 (1982).

    Google Scholar 

  70. R. M. Bystrova and Yu. M. Yutilov, Khim. Geterotsikl. Soedin., No. 6, 953 (1968).

    Google Scholar 

  71. B. M. Lynch and B. P. L. Lom, J. Heterocycl. Chem., 11, 223 (1974).

    Google Scholar 

  72. W. W. Paudler and J. N. Chasman, J. Heterocycl. Chem., 10, 499 (1973).

    Google Scholar 

  73. J. D. Teulade, R. Escale, G. Grassy, J. P. Girard, and J. P. Chapat, Bull. Soc. Chim. France, Part 2, No. 9–10, 529 (1979).

    Google Scholar 

  74. G. Saint-Ruf, B. Loukakou, and C. N'Zouzi, J. Heterocycl. Chem., 18, 1565 (1981).

    Google Scholar 

  75. R. Nutiu and I. Sebe, Rev. Roum. Chim., 16, 919 (1971).

    Google Scholar 

  76. D. J. Brown, J. Appl. Chem., 2, 239 (1952).

    Google Scholar 

  77. R. A. Ling, T. R. Matthews, and R. K. Robins, J. Med. Chem., 19, 1072 (1976).

    Google Scholar 

  78. C. D. Johnson and A. R. Katritzky, J. Chem. Soc., No. 1, (1971).

  79. D. E. O'Brien, C. C. Cheng, and S. Pfleiderer, J. Med. Chem., 9, 573 (1966).

    Google Scholar 

  80. D. J. Brown, J. Soc. Chem. Ind., 69, 353 (1950).

    Google Scholar 

  81. D. J. Brown, Proc. Royal. Aust. Chem. Inst., 33, 57 (1966).

    Google Scholar 

  82. I. Wempen, H. U. Blank, and J. J. Fox, J. Heterocycl. Chem., 6, No. 4, 593 (1969).

    Google Scholar 

  83. K. Baeyer, Annalen, 127, 199 (1863).

    Google Scholar 

  84. W. Trcinski, Berichte, 16, 1057 (1883).

    Google Scholar 

  85. H. Blitz and K. Sedlatscheck, Berichte, 57, 339 (1924).

    Google Scholar 

  86. R. Bartling, Annalen, 339, 37 (1905).

    Google Scholar 

  87. K. Baeyer, Annalen, 135, 312 (1865).

    Google Scholar 

  88. D. J. Brown, J. Appl. Chem., 9, 203 (1959).

    Google Scholar 

  89. D. J. Brown, J. Appl. Chem., 7, 109 (1957).

    Google Scholar 

  90. D. J. Brown, E. Hoeger, and S. F. Mason, J. Chem. Soc., No. 1, 211 (1955).

    Google Scholar 

  91. J. L. Rabinowitz and S. Gurin, J. Am. Chem. Soc., 75, 5758 (1953).

    Google Scholar 

  92. C. Cenda, H. Idzumi, and M. Kano, Annu. Proc. Coll. Pharmacy, No. 11, 62 (1961). Ref. Zh. Zhim., 24Zh362 (1962).

    Google Scholar 

  93. R. K. Robins, F. W. Furcht, A. D. Grauer, and J. W. Jonnes, J. Am. Chem. Soc., 78, 2418 (1956).

    Google Scholar 

  94. H. Kano and T. Makimsumi, Japanese Patent No. 5946; Ref. Zh. Khim., 14N281 (1964).

  95. Y. Makisumi, Chem. Pharm. Bull., 9, 873 (1961).

    Google Scholar 

  96. B. M. Lynch, M. A. Khan, S. C. Sharma, and H. C. Teo, Can. J. Chem., 53, 119 (1975).

    Google Scholar 

  97. A. Ohta, T. Watanabe, Y. Akita, and T. Kurihara, Hukusokau Kagaku Toronkai Koen Yoshishu, 84 (1975); Chem. Abs., 84, 164723 (1976).

  98. G. Karmas and P. E. Spoerri, J. Am. Chem. Soc., 75, 5517 (1953).

    Google Scholar 

  99. G. Karmas and P. E. Spoerri, J. Am. Chem. Soc., 78, 4071 (1956).

    Google Scholar 

  100. D. S. Donald, U. S. Patent No. 3808209; Ref. Zh. Khim., 7N246 (1975).

  101. S. Dikson and L. F. Wiggins, J. Chem. Soc., No. 10, 3235 (1950).

    Google Scholar 

  102. T. Itai and S. Suzuki, Chem. Pharm. Bull., 8, 999 (1960).

    Google Scholar 

  103. D. L. Aldous and R. N. Castle, Arzneimittel Forsch., 13, 878 (1963).

    Google Scholar 

  104. W. D. Guinther, D. G. Clark, and R. N. Castle, J. Heterocycl. Chem., 2, 67 (1965).

    Google Scholar 

  105. M. Yanai, T. Kinoshita, S. Takeda, H. Sadaki, and H. Watanabe, Chem. Pharm. Bull., 18, 1680 (1970).

    Google Scholar 

  106. R. D. Thompson and R. N. Castle, J. Heterocycl. Chem., 18, 1523 (1981).

    Google Scholar 

  107. H. E. Baumgarten, J. Am. Chem. Soc., 77, 5109 (1955).

    Google Scholar 

  108. T. Terai, H. Azuma, and R. Hattori, Japanese Patent No. 1299; Chem. Abs., 66, 65499 (1967).

    Google Scholar 

  109. T. Terai, H. Azuma, and R. Hattori, Japanese Patent No. 1300; Chem. Abs., 66, 65497 (1967).

    Google Scholar 

  110. M. Takay, K. Terashima, and K. Ozeki, Takugaku Zasshi, 98, 1472 (1978); Chem. Abs., 90, 152105 (1979).

    Google Scholar 

  111. T. Itai and S. Natsume, Chem. Pharm. Bull., 11, 83 (1963).

    Google Scholar 

  112. T. Nakagome, Yakugaku Dzassi, 82, 253 (1962); Ref. Zh. Khim., 1963, 8Zh281.

    Google Scholar 

  113. T. Itai and S. Sako, Chem. Pharm. Bull., 9, 149 (1961).

    Google Scholar 

  114. S. Sako, Chem. Pharm. Bull., 11, 337 (1963).

    Google Scholar 

  115. T. Itai and S. Sako, Chem. Pharm. Bull., 14, 269 (1966).

    Google Scholar 

  116. H. Igeta, T. Tsuciya, M. Nakajima, T. Seikya, Y. Kumaki, T. Nakai, and T. Nojima, Chem. Pharm. Bull., 17, 756 (1969).

    Google Scholar 

  117. P. D. Cook and R. N. Castle, J. Heterocycl. Chem., 10, 551 (1973).

    Google Scholar 

  118. H. Igeta, Chem. Pharm. Bull., 8, 550 (1960).

    Google Scholar 

  119. M. Yanai, T. Kinoshita, and S. Takeda, Chem. Pharm. Bull., 19, 2181 (1971).

    Google Scholar 

  120. T. Itai and S. Natsume, Chem. Pharm. Bull., 11, 342 (1963).

    Google Scholar 

  121. T. Itai and S. Natsume, Chem. Pharm. Bull., 12, 223 (1964).

    Google Scholar 

  122. S. Kamjya and M. Tanno, Chem. Pharm. Bull., 23, 923 (1975).

    Google Scholar 

  123. M. Nakadate, S. Sueyoshi, and S. Suzuki, Chem. Pharm. Bull., 18, 1211 (1970).

    Google Scholar 

  124. S. Sueyoshi and I. Susuki, Chem. Pharm. Bull., 23, 2772 (1975).

    Google Scholar 

  125. D. H. Rosenblat, W. H. Dennis, and R. D. Goodin, J. Am. Chem. Soc., 95, 2133 (1973).

    Google Scholar 

  126. T. J. Broxton, D. M. Muir, and A. J. Parker, J. Org. Chem., 40, 2037 (1975).

    Google Scholar 

  127. T. J. Broxton, D. M. Muir, and A. J. Parker, J. Org. Chem., 40, 3230 (1975).

    Google Scholar 

  128. V. A. Ustinov, V. V. Plakhtinskii, G. S. Mironov, and N. S. Ryabukhina, Zh. Org. Khim., 25, 1775 (1979).

    Google Scholar 

  129. H. Finger, J. Prakt. Chem., 75, 103 (1907).

    Google Scholar 

  130. N. B. Galstukhova, G. S. Predvoditeleva, I. M. Berzina, T. Yu. Kartseva, M. N. Shchukina, and G. N. Pershin, Khim.-Farm. Zh., No. 4, 7 (1969).

    Google Scholar 

  131. F. Reicheneder and K. Dury, French Patent No. 1384304; Chem. Abs., 62, 16265 (1965).

    Google Scholar 

  132. A. N. Frolov, A. V. El'tsov, and O. V. Kul'bitskaya, Khim. Geterotsikl. Soedin., No. 12, 1645 (1974).

    Google Scholar 

  133. R. Shaipro, J. Am. Chem. Soc., 84, 2948 (1964).

    Google Scholar 

  134. S. D. Carter and G. W. H. Cheesman, Tetrahedron, 33, 827 (1977).

    Google Scholar 

  135. H. M. Feuer (editor), Chemistry of the Nitro and Nitrose Groups, Wiley (1970).

  136. W. D. Emmons, J. Am. Chem. Soc., 79, 5528 (1957).

    Google Scholar 

  137. E. Brown, J. Am. Chem. Soc., 76, 3167 (1954).

    Google Scholar 

  138. A. Kirpal and W. Böhm, Berichte, 65, 680 (1932).

    Google Scholar 

  139. R. H. Wiley and I. L. Hertman, J. Am. Chem. Soc., 73, 494 (1951).

    Google Scholar 

  140. B. Stanovnik, M. Tisler, and A. Pollak, J. Org. Chem., 35, 2478 (1970).

    Google Scholar 

  141. E. C. Taylor and A. McKillop, J. Org. Chem., 30, 3153 (1965).

    Google Scholar 

  142. E. C. Taylor, Tseng Chi-Ping, and J. B. Rampal, J. Org. Chem., 47, 552 (1982).

    Google Scholar 

  143. A. Garming, D. Redwan, P. Gelbke, D. Kern, and U. Direks, Annalen, No. 7, 1744 (1975).

    Google Scholar 

  144. A. Dornow and H. von Plesen, Chem. Ber., 99, 244 (1966).

    Google Scholar 

  145. P. E. Fanta and R. A. Stein, J. Am. Chem. Soc., 77, 1045 (1955).

    Google Scholar 

  146. P. F. H. Freeman, U. S. Patent No. 3674877; Chem. Abs., 77, 88314 (1972).

    Google Scholar 

  147. P. E. Fanta, J. Am. Chem. Soc., 75, 737 (1953).

    Google Scholar 

  148. D. J. Collins, J. Chem. Soc., No. 2, 1337 (1963).

    Google Scholar 

  149. P. E. Fanta and R. A. Stein, Chem. Rev., 60, 261 (1960).

    Google Scholar 

  150. T. C. Lee and G. Salemnik, J. Org. Chem., 40, 3608 (1975).

    Google Scholar 

  151. R. Bernetti, F. Mansini, and C. C. Price, J. Org. Chem., 27, 2863 (1962).

    Google Scholar 

  152. A. Broderick and D. G. Wibberley, J. Chem. Soc., Perkin Trans I, No. 10, 1910 (1975).

    Google Scholar 

  153. V. L. Rusinov, A. Yu. Petrov, and I. Ya. Postovskii, in: Chemistry of Dicarbonyl Compounds [in Russian], Riga (1981), p. 195.

  154. S. M. Kvitko, V. V. Perekalin, and N. V. Buival, Zh. Org. Khim., 2, 2253 (1966).

    Google Scholar 

  155. Yu. V. Maksimov and S. M. Kvitko, in: Some Aspects of the Chemistry of Rare-Earth Elements [in Russian], Barnaul'skii Pedinstitut, Barnaul (1975), p. 58.

    Google Scholar 

  156. E. M. Hawes and D. G. Wibberley, J. Chem. Soc. C, No. 3, 315 (1966).

    Google Scholar 

  157. Zh. A. Krasnaya, T. S. Statsenko, E. P. Prokof'ev, I. P. Yakovlev, and V. F. Kucherov, Izv. Akad. Nauk SSSR, Ser. Khim., No. 4, 845 (1974).

    Google Scholar 

  158. A. Dornow and W. Sassenberg, Annalen, 602, 14 (1957).

    Google Scholar 

  159. H. E. Baumgarten and J. L. Saylor, J. Am. Chem. Soc., 79, 1502 (1957).

    Google Scholar 

  160. D. W. Ockenden and K. Schofield, J. Chem. Soc., No. 12, 3914 (1953).

    Google Scholar 

  161. K. Schofield and R. S. Theobald, J. Chem. Soc., No. 1, 395 (1950).

    Google Scholar 

  162. G. B. Bryant, D. E. Wolton, G. L. Jenkins, and J. E. Christian, J. Am. Chem. Soc., 69, 365 (1947).

    Google Scholar 

  163. H. Schäfer, K. Gewald, and M. Seifert, J. Prakt. Chem., 318, 39 (1976).

    Google Scholar 

  164. H. Schäfer, B. Bartho, and K. Gewald, Z. Chem., 13, 294 (1973).

    Google Scholar 

  165. H. Schäfer and K. Gewald, Z. Chem., 18, 335 (1978).

    Google Scholar 

  166. H. Schäfer and K. Gewald, Z. Chem., 16, 272 (1976).

    Google Scholar 

  167. W. J. Hale and H. C. Brill, J. Am. Chem. Soc., 34, 82 (1912).

    Google Scholar 

  168. R. O. Robin, R. S. Winnek, and J. P. Englisch, J. Am. Chem. Soc., 64, 567 (1942).

    Google Scholar 

  169. P. E. Fanda and E. A. Hedman, J. Am. Chem. Soc., 78, 1434 (1956).

    Google Scholar 

  170. M. P. L. Caton, D. T. Hurst, J. F. W. McOmie, and R. R. Hunt, J. Chem. Soc. C, No. 13, 1204 (1967).

    Google Scholar 

  171. D. T. Hurst and J. Christophides, Heterocycles, 6, 1999 (1977).

    Google Scholar 

  172. R. Andrisano and G. Modena, Bull. Sci. Fac. Chim. Int. Bologna, 10, 156 (1952); Chem. Abs., 47, 4737 (1953).

    Google Scholar 

  173. Y. Rahamin, J. Sharvit, A. Mandelbaum, and M. Sprecher, J. Org. Chem., 32, 3856 (1967).

    Google Scholar 

  174. A. Guiliana, L. Bernardi, M. Foglio, A. Glaesser, and H. Temperilli, Pat. 2259012 (BRD); Chem. Abs., 79, 53660 (1973).

    Google Scholar 

  175. M. P. V. Boarland and J. F. W. McOmie, J. Chem. Soc., No. 3, 1218 (1951).

    Google Scholar 

  176. M. P. L. Caton and J. F. W. McOmie, J. Chem. Soc., C, No. 7, 836 (1968).

    Google Scholar 

  177. Yu. V. Maksimov, in: Some Aspects of the Chemistry of Rare-Earth Elements [in Russian], Barnaul'skii Pedinstitut, Barnaul (1975), p. 86.

    Google Scholar 

  178. Yu. V. Maksimov and V. N. Aleinikov, in: Some Aspects of the Chemistry of Rare-Earth Elements [in Russian], Barnaul'skii Pedinstitut, Barnaul (1975), p. 75.

    Google Scholar 

  179. V. L. Rusinov, I. Ya. Postovskii, A. Yu. Petrov, E. O. Sidorov, and Yu. A. Azev, Khim. Geterotsikl. Soedin., No. 11, 1554 (1981).

    Google Scholar 

  180. D. E. O'Breien, R. K. Robins, and L. N. Simon, U. S. Patent No. 3907799; Chem. Abs., 84, 4998 (1976).

    Google Scholar 

  181. Y. Makisumi, Chem. Pharm. Bull., 9, 801 (1961).

    Google Scholar 

  182. R. Nutiu and I. Sebe, Rev. Roum. Chim., 16, 919 (1971).

    Google Scholar 

  183. R. Nutiu, I. Sebe, and M. Nutiu, Rev. Roum. Chim., 19, 860 (1974).

    Google Scholar 

  184. O. S. Wolfbeis, Chem. Ber., 100, 2480 (1977).

    Google Scholar 

  185. M. Prystas and J. Gut, 28, 2501 (1963).

    Google Scholar 

  186. H. Vorbrüggen and P. Strehlke, Chem. Ber., 106, 3030 (1973).

    Google Scholar 

  187. G. Simchen, Angew Chem., 19, 860 (1964).

    Google Scholar 

  188. S. Rajappa, R. Sreenivasan, B. G. Advani, R. H. Summerville, and R. Hoffmann, Indian J. Chem., 15B, 297 (1977).

    Google Scholar 

  189. Z. D. Dubovenko and V. P. Mamaev, Izv. Sib. Otd. Akad. Nauk SSSR, Ser. Khim. Nauk, No. 3, 101 (1972).

    Google Scholar 

  190. T. Urbanski, Z. Bierncki, and E. Lipska, Roczn. Chem., 28, 169 (1954).

    Google Scholar 

  191. T. Urbanski and E. Lipska, Roczn. Chem., 26, 182 (1952).

    Google Scholar 

  192. H. Artus, “Über acyklische und heterocyclische Alkylation und Amino-alkylation,” Dissertation, Hamburg (1977).

  193. T. Severin, B. Brück, and P. Adhikary, Chem. Ber., 99, 3097 (1966).

    Google Scholar 

  194. A. Aydin and H. Feuer, Chim. Acta Turcica, 7, 121 (1979).

    Google Scholar 

  195. A. Aydin and H. Feuer, Chim. Acta Turcica, 9, 199 (1981).

    Google Scholar 

  196. H. Hamberger, H. Reinshagen, G. Schulz, and G. Sigmund, Tetrahedron Lett., No. 41, 3619 (1977).

    Google Scholar 

  197. H. E. Baumgarten and M. R. DeBruner, J. Am. Chem. Soc., 76, 3489 (1954).

    Google Scholar 

  198. H. E. Baumgarten and D. L. Pederson, J. Am. Chem. Soc., 80, 1977 (1958).

    Google Scholar 

  199. H. Neunhoffer, Chemistry of 1,2,3-Triazines, 1,2,4-Triazines, Tetrazines, and Pentazines, Wiley, New York (1978).

    Google Scholar 

  200. H. Schäfer and K. Gewald, J. Prakt. Chem., 322, 87 (1980).

    Google Scholar 

  201. V. L. Rusinov, A. Yu. Petrov, and I. Ya. Postovskii, Khlm. Geterotsikl. Soedin., No. 9, 1283 (1980).

    Google Scholar 

  202. V. L. Rusinov, A. Yu. Petrov, and 0. N. Chupakhin, in: Nucleophilic Reactions of Carbonyl Compounds fin Russian], Saratov (1982), p. 36.

  203. W. E. Hahn and H. Zawadsk, Roczn. Chem., 38, 557 (1964).

    Google Scholar 

  204. A. I. Dychenko and L. S. Pupko, Ukr. Khim. Zh., 40, 1220 (1974).

    Google Scholar 

  205. A. I. Dychenko, L. S. Pupko, and P. S. Pel'kis, Zh. Geterotsikl. Soedin., No. 9. 1290 (1975).

    Google Scholar 

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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 2, pp. 147–165, February, 1985.

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Rusinov, V.L., Petrov, A.Y. & Chupakhin, O.N. Nitroazines. Methods of synthesis (review). Chem Heterocycl Compd 21, 113–131 (1985). https://doi.org/10.1007/BF00504191

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