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Nontraditional nitrogen-containing macroheterocyclic systems with a high degree of conjugation (review)

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Chemistry of Heterocyclic Compounds Aims and scope

Abstract

Methods for the classification and codification of the principal types of nitrogen-containing macroheterocyclic systems with a high degree of conjugation and the schemes for their synthesis are presented.

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Literature cited

  1. M. C. Thompson and D. H. Busch, J. Am. Chem. Soc., 86, 213 (1964).

    Google Scholar 

  2. L. D. Nichols and A. S. Obermayer, U.S. Patent No. 3481945; Chem. Abstr., 72, 56703 (1970).

    Google Scholar 

  3. G. Muehmel and E. Breitmaier, Angew. Chem., 90, 818 (1978).

    Google Scholar 

  4. R. Mueller and D. Woehrle, Makromol. Chem., 176, 2775 (1975).

    Google Scholar 

  5. G. A. Melson and D. H. Busch, J. Am. Chem. Soc., 87, 1706 (1965).

    Google Scholar 

  6. S. C. Gummings and D. H. Busch, J. Am. Chem. Soc., 92, 1924 (1970).

    Google Scholar 

  7. G. Hawley and E. L. Blinn, Inorg. Chem., 14, 2865 (1975).

    Google Scholar 

  8. D. S. C. Black and N. E. Rothnie, Tetrahedron Lett., No. 31, 2835 (1978).

    Google Scholar 

  9. D. S. C. Black, N. E. Rothnie, and L. C. Wong, Tetrahedron Lett., 21, 1883 (1980).

    Google Scholar 

  10. C.-P. Eherensperger, M. Heberlein, and P. Skrabal, Helv. Chim. Acta, 61, 2813 (1978).

    Google Scholar 

  11. I. Kohlmeyer, E. Lorch, G. Bauer, and E. Breitmaier, Chem. Ber., 111, 2919 (1978).

    Google Scholar 

  12. C. L. Honeybourne and P. Burchill, Inorg. Synth., 18, 44 (1978).

    Google Scholar 

  13. H. Hiller, P. Dimroth, and H. Pfitzner, Lieb. Ann., 717, 137 (1968).

    Google Scholar 

  14. A. P. Gulter and D. Dolphin, J. Coord. Chem., 6, 59 (1976).

    Google Scholar 

  15. A. Pezeshk, F. T. Greenaway, and G. Vincow, Inorg. Chem., 17, 3421 (1978).

    Google Scholar 

  16. Y.-M. Wuu, S.-M. Peng, and H. Chang, J. Inorg. Nucl. Chem., 42, 839 (1980).

    Google Scholar 

  17. E.-G. Jaeger, Zeitschr. Anorg. Chem., 364, 177 (1969).

    Google Scholar 

  18. F. Hanic, M. Handloviĉ, and O. Lindgren, Collect. Czech. Chem. Commun., 32, 2119 (1972).

    Google Scholar 

  19. V. L. Goedken and S.-M. Peng, Chem. Commun., No. 10, 337 (1973).

    Google Scholar 

  20. F. L'Eplattenier and A. Pugin, Helv. Chim. Acta, 58, 917 (1975).

    Google Scholar 

  21. D. S. C. Black, West German Patent No. 2533808; Chem. Abstr., 85, 34631 (1976).

    Google Scholar 

  22. R. Mueller and D. Woehrle, Makromol. Chem., 179, 2161 (1978).

    Google Scholar 

  23. S. Ogawa, J. Chem. Soc., Perkin Trans. 1, No. 2, 214 (1977).

    Google Scholar 

  24. E. Lorch and E. Breitmaier, Chem. Ztg., 101, 262 (1977).

    Google Scholar 

  25. S. F. Gait, M. E. Peek, C. W. Rees, and C. R. Storr, J. Chem. Soc., Perkin Trans. 1, No. 11, 1248 (1974).

    Google Scholar 

  26. M. M. Bishop, J. Lewis, T. D. O'Donoghue, and P. R. Raithby, Chem. Commun., No. 11, 476. (1978).

    Google Scholar 

  27. V. M. Dziomko, B. K. Berestevich, A. V. Kessenikh, Yu. S. Ryabokobylko, and R. S. Kuzanyan, Khim. Geterotsikl. Soedin., No. 8, 1097 (1978).

    Google Scholar 

  28. V. M. Dziomko, L. G. Fedosyuk, K. A. Dunaevskaya, Yu. S. Ryabokobylko, A. V. Kessenikh, R. V. Poponova, and R. S. Kuzanyan, Khim. Geterotsikl. Soedin., No. 9, 1258 (1979).

    Google Scholar 

  29. V. M. Dziomko, M. N. Stopnikoya, and Yu. S. Ryabokobylko, Khim. Geterotsikl. Soedin., No. 6, 837 (1980).

    Google Scholar 

  30. O. Manabe, T. Sone, H. Imai, Y. Matsushima, and S. Shinkai, Nippon Kagaku Kaishi, No. 7, 1154 (1980).

    Google Scholar 

  31. V. M. Dziomko and U. A. Tomsons, Khim. Geterotsikl. Soedin., No. 5, 669 (1976).

    Google Scholar 

  32. V. M. Dziomko, U. A. Tomsons, Yu. S. Ryabokobylko, R. S. Kuzanyan, and R. V. Poponova, Koord. Khim., 3, 1743 (1977).

    Google Scholar 

  33. V. M. Dziomko, U. A. Tomsons, R. S. Kuzanyan, and Yu. S. Ryabokobylko, Zh. Vses. Khim. Ova., 22, 115 (1977).

    Google Scholar 

  34. V. M. Dziomko, U. A. Tomsons, and Yu. S. Ryabokobylko, Khim. Geterotsikl. Soedin., No. 7, 968 (1976).

    Google Scholar 

  35. V. M. Dziomko, M. N. Stopnikova, L. V. Shmelev, Yu. S. Ryabokobylko, G. M. Adamova, M. Z. Gurevich, and R. V. Poponova, Khim. Geterotsikl. Soedin., No. 4, 546 (1981).

    Google Scholar 

  36. V. M. Dziomko, L. G. Fedosyuk, and K. A. Dunaevskaya, Zh. Obshch. Khim., 46 2488 (1975).

    Google Scholar 

  37. V. M. Dziomko, L. G. Fedosyuk, K. A. Dunaevskaya, and Yu. S. Ryabokobylko, Koord. Khim., 2, No. 1, 39 (1976).

    Google Scholar 

  38. V. M. Dziomko, B. K. Berestevich, A. V. Kessenikh, V. A. Olikova, and R. S. Kuzanyan, Khim. Geterotsikl. Soedin., No. 11, 1530 (1980).

    Google Scholar 

  39. V. M. Dziomko and U. A. Tomsons, Reak. Osobo Chistye Veshchestva. Tr. IREA, 38, 203 (1976).

    Google Scholar 

  40. V. L. Goedken, Y. Park, S.-M. Peng, and J. A. M. Norris, J. Am. Chem. Soc., 96, 7693 (1974).

    Google Scholar 

  41. W. Radecka-Paryzek, Inorg. Chim. Acta, 34, 5 (1979).

    Google Scholar 

  42. W. Radecka-Paryzek, Inorg. Chim. Acta, 35, L349 (1979).

    Google Scholar 

  43. V. M. Dziomko, B. K. Berestevich, A. V. Kessenikh, Yu. S. Ryabokobylko, and R. S. Kuzanyan, Khim. Geterotsikl. Soedin., No. 5, 701 (1979).

    Google Scholar 

  44. V. M. Dziomko and B. K. Berestevich, Koord. Khim., 6, 142 (1980).

    Google Scholar 

  45. S. Ogawa, T. Yamaguchi, and N. Gotoh, J. Chem. Soc., Perkin Trans. 1, No. 9, 976 (1974).

    Google Scholar 

  46. S. Ogawa and S. Shiraishi, J. Chem. Soc., Perkin Trans. 1, No. 11, 2527 (1980).

    Google Scholar 

  47. V. L. Goedken and S.-M. Peng, Chem. Commun., No. 3, 62 (1973).

    Google Scholar 

  48. V. L. Goedken and S.-M. Peng, J. Am. Chem. Soc., 95, 5773 (1973).

    Google Scholar 

  49. D. S. C. Black and A. J. Hartshorn, Aust. J. Chem., 29, 2271 (1976).

    Google Scholar 

  50. M. M. Bishop, J. Lewis, T. D. O'Donoghue, P. R. Raithby, and J. N. Ramsden, Chem. Commun., No. 19, 828 (1978).

    Google Scholar 

  51. M. M. Bishop, J. Lewis, T. D. O'Donoghue, and P. R. Raithby, J. Chem. Soc., Dalton, No. 8, 1390 (1980).

    Google Scholar 

  52. J. Lewis, T. D. O'Donoghue, and P. R. Raithby, J. Chem. Soc., Dalton, No. 8, 1383 (1980).

    Google Scholar 

  53. J. Lewis, T. D. O'Donoghue, Z. P. Haque, and P. A. Tasker, J. Chem. Soc., Dalton, No. 9, 1664 (1980).

    Google Scholar 

  54. Z. P. Haque, M. McPartlin, and P. A. Tasker, Inorg. Chem., 18, 2920 (1979).

    Google Scholar 

  55. J. S. Skuratowicz, I. L. Madden, and D. H. Busch, Inorg. Chem., 16, 1721 (1977).

    Google Scholar 

  56. J. D. Goddard and T. Norris, Inorg. Nucl. Chem. Lett., 14, 211 (1978).

    Google Scholar 

  57. I. W. Pang and D. V. Stynes, Inorg. Chem., 16, 2192 (1977).

    Google Scholar 

  58. A. M. Tait and D. H. Busch, Inorg. Synth., 18, 30 (1978).

    Google Scholar 

  59. S. Brawner and K. B. Mertes, J. Inorg. Nucl. Chem., 41, 764 (1979).

    Google Scholar 

  60. M. D. Timken, R. T. Sheldon, W. G. Rohly, and K. B. Mertes, J. Am. Chem. Soc., 102, 4716 (1980).

    Google Scholar 

  61. C. L. Honeybourne, Inorg. Nucl. Chem. Lett., 11, 191 (1975).

    Google Scholar 

  62. J. de O. Cabral, M. F. Cabral, W. J. Cummins, M. G. B. Drew, A. Rodgers, and S. M. Nelson, Inorg. Chim. Acta, 30, L313 (1978).

    Google Scholar 

  63. M. G. B. Drew, J. de O. Cabral, M. F. Cabral, F. S. Esho, and S. M. Nelson, Chem. Commun., No. 22, 1033 (1979).

    Google Scholar 

  64. R. W. Stotz and R. C. Stoufer, Chem. Commun., No. 24, 1682 (1970).

    Google Scholar 

  65. V. M. Dziomko, V. M. Ostrovskaya, and T. E. Zhukova, Khim. Geterotsikl. Soedin., No. 8, 1039 (1979).

    Google Scholar 

  66. K. Sakata, M. Hashimoto, N. Tagami, and Y. Murakami, Bull. Chem. Soc. Jpn., 53, 2262 (1980).

    Google Scholar 

  67. V. L. Goedken, J. Molin-Chase, and Y. Whang, Chem. Commun., No. 10, 337 (1973).

    Google Scholar 

  68. G. M. Coppola, G. Hardtman, and B. S. Huesi, J. Heterocycl. Chem., 11, 51 (1974).

    Google Scholar 

  69. C. Reichardt and W. Schebelein, Z. Naturforsch., 33, 1012 (1978).

    Google Scholar 

  70. M. Hunziker, B. Hilti, and G. Rihs, Helv. Chim. Acta, 84, 82 (1981).

    Google Scholar 

  71. K. Rustmeier and E. Breitmeier, Chem. Ztg., 103, 154 (1979).

    Google Scholar 

  72. E. Lorch and E. Breitmeier, Chem. Ztg., 99, 87 (1975).

    Google Scholar 

  73. R. Kruse and E. Breitmeier, Chem. Ber., 114, 832 (1981).

    Google Scholar 

  74. D. A. Place, G. P. Ferrara, J. J. Harland, and J. C. Dabrowiak, J. Heterocycl. Chem., 17, 439 (1980).

    Google Scholar 

  75. Y. Nishida, A. Sumita, K. Hayashida, H. Ohshima, S. Kida, and Y. Maeda, J. Coord. Chem., 9, 161 (1979).

    Google Scholar 

  76. F. L'Eplattenier and A. Pugin, West German Patent No. 2260761; Chem. Abstr., 81, 27183 (1974).

    Google Scholar 

  77. T. J. Truex and R. H. Holm, J. Am. Chem. Soc., 94, 4529 (1972).

    Google Scholar 

  78. M. Millar and R. H. Holm, Chem. Commun., No. 5, 169 (1975).

    Google Scholar 

  79. S.-M. Peng, J. A. Ibers, M. Millar, and R. H. Holm, J. Am. Chem. Soc., 98, 8037 (1976).

    Google Scholar 

  80. S. C. Tang and R. H. Holm, J. Am. Chem. Soc., 97, 3359 (1975).

    Google Scholar 

  81. D. S. C. Black, A. J. Hartshorn, M. Horner, and S. Huenig, Aust. J. Chem., 30, 2493 (1977).

    Google Scholar 

  82. S.-M. Peng and V. L. Goedken, J. Am. Chem. Soc., 98, 8500 (1976).

    Google Scholar 

  83. G. C. Gordon, S.-M. Peng, and V. L. Goedken, Inorg. Chem., 17 3578 (1978).

    Google Scholar 

  84. S. G. McGeachin, Can. J. Chem., 44, 2324 (1966).

    Google Scholar 

  85. A. R. Cutler and D. Dolphin, Can. J. Chem., 55, 3062 (1977).

    Google Scholar 

  86. D. G. Farnum and K. Rasheed, J. Org. Chem., 42, 573 (1977).

    Google Scholar 

  87. R. Mueller and D. Woehrle, Makromol. Chem., 177, 2241 (1976).

    Google Scholar 

  88. G. P. Ferrara and J. C. Dabrowiak, Inorg. Nucl. Chem. Lett., 14, 223 (1978).

    Google Scholar 

  89. F. C. McElroy and J. C. Dabrowiak, J. Am. Chem. Soc., 98, 7112 (1976).

    Google Scholar 

  90. M. C. Weiss and V. L. Goedken, J. Am. Chem. Soc., 98, 3389 (1976).

    Google Scholar 

  91. M. C. Weiss, B. Bursten, S.-M. Peng, and V. L. Goedken, J. Am. Chem. Soc., 98, 8021 (1976).

    Google Scholar 

  92. V. L. Goedken, S.-M. Peng, J. A. Molin-Norris, and Y. -A. Park, J. Am. Chem. Soc., 98, 8391 (1976).

    Google Scholar 

  93. M. C. Weiss and V. L. Goerken, Inorg. Chem., 18 274 (1979).

    Google Scholar 

  94. A. Pezeshk, F. T. Greenaway, J. C. Dabrowiak, and G. Vincow, Inorg. Chem., 17, 1717 (1978).

    Google Scholar 

  95. V. L. Goedken, J. J. Pluth, S.-M. Peng, and B. Bursten, J. Am. Chem. Soc., 98, 8014 (1976).

    Google Scholar 

  96. M. C. Weiss and V. L. Goedken, Chem. Commun., No. 14, 531 (1976).

    Google Scholar 

  97. V. L. Godeken, S.-M. Peng, and Y. Park, J. Am. Chem. Soc., 96, 284 (1974).

    Google Scholar 

  98. G. P. Ferrara and J. C. Dabrowiak, Inorg. Nucl. Chem. Lett., 14, 31 (1978).

    Google Scholar 

  99. D. P. Fisher, V. Piermattie, and J. C. Dabrowiak, J. Am. Chem. Soc., 99, 2811 (1977).

    Google Scholar 

  100. J. Eilmes and E. Sledziewska, Bull. Acad. Pol., Ser, Sci. Chem., 26, 441 (1978).

    Google Scholar 

  101. J. C. Dabrowiak, D. P. Fisher, F. C. McElroy, and D. J. Macero, Inorg. Chem., 18, 2304 (1979).

    Google Scholar 

  102. D. P. Fisher, F. C. McElroy, D. J. Macero, and J. -C. Dabrowiak, Inorg. Nucl. Chem. Lett., 12, 435 (1976).

    Google Scholar 

  103. J. D. Goddard, Inorg. Nucl. Chem. Lett., 13, 555 (1977).

    Google Scholar 

  104. L. T. Taylor, F. L. Urbach, and D. H. Busch, J. Am. Chem. Soc., 91, 1072 (1969).

    Google Scholar 

  105. V. Katovič, L. T. Taylor, and D. H. Busch, J. Am. Chem. Soc., 91, 2122 (1969).

    Google Scholar 

  106. V. Katoviĉ, L. T. Taylor, and D. H. Busch, Inorg. Chem., 10, 458 (1971).

    Google Scholar 

  107. K. B. Yatsimirskii and A. G. Kol'chinskii, Dokl. Akad. Nauk SSSR, 246, 895 (1979).

    Google Scholar 

  108. S. M. Nelson, F. S. Esho, M. G. B. Drew, and P. Bird, Chem. Commun., No. 22, 1035 (1979).

    Google Scholar 

  109. M. C. Weiss, G. C. Gordon, and V. L. Goedken, J. Am. Chem. Soc., 101, 857 (1979).

    Google Scholar 

  110. K. M. Kadish, D. Schaeper, L. A. Bottomley, M. Tsutsui, and R. L. Bobseine, J. Inorg. Nucl. Chem., 42, 469 (1980).

    Google Scholar 

  111. F. G. McElroy, J. C. Dabrowiak, and D. T. Masero, Inorg. Chem., 16, 947.

  112. F. V. Lovecchio, E. S. Gore, and D. H. Busch, J. Am. Chem, Soc., 96, 3109 (1974).

    Google Scholar 

  113. L. -S. Lin, T. J. Marks, C. R. Kannewurf, J. W. Lyding, M. S. McClure, M. T. Ratajack, and T. C. Whang, Chem. Commun., No. 20, 954 (1980).

    Google Scholar 

  114. A. J. Jircitano, M. D. Timken, K. B. Mertes, and J. R. Ferraro, J. Am. Chem. Soc., 101, 7661 (1979).

    Google Scholar 

  115. P. Cassoux, L. Interante, and J. Kasper, Compt. Rend., C, 297, 25 (1980).

    Google Scholar 

  116. M. F. Perutz, Sci. Am., 239, 68 (1978).

    Google Scholar 

  117. J. E. Baldwin and J. Huff, J. Am. Chem. Soc., 95, 5757 (1973).

    Google Scholar 

  118. R. G. Little, J. A. Bers, and J. E. Baldwin, J. Am. Chem. Soc., 97, 7049 (1975).

    Google Scholar 

  119. W. M. Reiff, H. Wong, J. E. Baldwin, and J. Huff, Inorg. Chem. Acta, 25, 91 (1977).

    Google Scholar 

  120. G. Zimmermann, H. Jahnke, H. Magenau, and D. Baresel, West German Patent No. 2334709; Chem. Abstr., 83, 82583 (1975).

    Google Scholar 

  121. K. A. Padyushkina, M. R. Tarasevich, and É. A. Akhundov, Elektrokhimiya, 15, 1884 (1979).

    Google Scholar 

  122. F. Beck, W. Dammert, J. Heiss, H. Hiller, and R. Polster, Z. Naturforsch., 28A, 1009. (1973).

    Google Scholar 

  123. F. Van den Brink, E. Barendrecht, and W. Visscher, Rec. Trav. Chlm., 99, 253 (1980).

    Google Scholar 

  124. H. Alt, H. Binder, and G. Sandstede, J. Catal., 28, 8 (1973).

    Google Scholar 

  125. H. Kast, H. Baumann, U. Mayer, and A. Oberlinner, West German Patent No. 2138931; Chem. Abstr., 78, 137964 (1973).

    Google Scholar 

  126. H. Kast, H. Baumann, U. Mayer, and A. Oberlinner, West German Patent No. 2152703; Chem. Abstr., 79, 6792 (1973).

    Google Scholar 

  127. H. Kast, H. Baumann, U. Mayer, and A. Oberlinner, West German Patent No. 2226963; Chem. Abstr., 83, 61715 (1975).

    Google Scholar 

  128. CIBA-GEIGY A. -G., French Patent No. 2165542; Chem. Abstr., 81, 27183 (1974).

    Google Scholar 

  129. F. L'Eplattenier, Chimia, 33, 196 (1979).

    Google Scholar 

  130. V. M. Dziomko, L. G. Fedosyuk, K. A. Dunaevskaya, D. N. Pleshkanev, N. Yu. Bolotnikova, I. M. Arkhipova, N. I. Talanova, and É. I. Silina, USSR Inventor's Certificate No. 606871; Byull. Izobret., No. 18, 74 (1978).

  131. V. M. Dziomko, in: News in the Chemistry of Nitrogen-Containing Heterocycles [in Russian], Vol. 1, Zinatne, Riga (1979), p. 51.

    Google Scholar 

  132. T. Toda, H. Miyata, and K. Toei, Bunseki Kagaku, 28, 440, (1979).

    Google Scholar 

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  1. All-Union Scientific-Research Institute of Chemical Reagents and Ultrapure Chemical Substances, 107258, Moscow

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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 1, pp. 3–18, January, 1982.

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Dziomko, V.M. Nontraditional nitrogen-containing macroheterocyclic systems with a high degree of conjugation (review). Chem Heterocycl Compd 18, 1–14 (1982). https://doi.org/10.1007/BF00513279

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