Skip to main content
Log in

Oligooxatetraazacoronands (review)

  • Published:
Chemistry of Heterocyclic Compounds Aims and scope

Abstract

Information on methods of synthesis and the physicochemical and chemical properties of tetraazamacroheterocycles from classes of crown ethers, viz., amides and thioamides, urethanes, azomethines, formazans, and depsipeptides, that contain two or more oxygen atoms in their loops is correlated. The unique characteristics of their complexing with various groups of metals are noted.

This is a preview of subscription content, log in via an institution to check access.

Access this article

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. L. F. Lindoy, Chem. Soc. Rev., 4, 421 (1975).

    Google Scholar 

  2. F. Vögtle and E. Weber, Angew. Chem., Int. Ed., 18, 753 (1979).

    Google Scholar 

  3. G. W. Gokel, D. M. Dishong, R. A. Schultz, and V. J. Gatto, Synthesis, No. 12, 997 (1982).

    Google Scholar 

  4. E. Weber and F. Vögtle, Inorg. Chim. Acta, 45, 65 (1980).

    Google Scholar 

  5. M. Okahara, Chem. Ind., 33, 715 (1982).

    Google Scholar 

  6. F. Vögtle, E. Weber, and U. Elben, Kontakte, Merck (1980), No. 2, p. 36.

    Google Scholar 

  7. H. Maeda, S. Furuyoshi, Y. Nakatsuji, and M. Okahara, Bull. Chem. Soc. Hps., 56, 3073 (1983).

    Google Scholar 

  8. S. A. G. Högberg and D. J. Cram, J. Org. Chem., 40, 151 (1975).

    Google Scholar 

  9. C. J. Pedersen and M. H. Bromels, US Patent No. 3 847–949; Chem. Abstr., 82, 73049 (1975).

    Google Scholar 

  10. W. Rasshofer, W. Wehner, and F. Vögtle, Ann. Chem., No. 5, 916 (1976).

    Google Scholar 

  11. W. Rasshofer and F. Vögtle, Ann., No. 8, 1340 (1977).

    Google Scholar 

  12. A. V. Bogatskii, N. G. Luk'yanenko, S. S. Basok, and L. K. Ostrovskaya, in: 4th All-Union Symposium on Organic Synthesis [in Russian], Moscow (1984).

  13. A. V. Bogatskii (Bogatsky), N. G. Luk'yanenko (Lukyanenko), S. S. Basok (Basoc), and L. K. Ostrovskaya, Synthesis, No. 2, 138 (1984).

    Google Scholar 

  14. S. Imajo and K. Nakanishi, J. Am. Chem. Soc., 105, 2071 (1983).

    Google Scholar 

  15. S. Imaki, T. Nodzoe, K. Nakanishi, and K. K. Santori, Japanese Patent No. 58-121285; Ref. Zh. Khim., 13N229P (1984).

  16. I. Tabushi, H. Okino, and Y. Kuroda, Tetrahedron Lett., No. 48, 4339 (1976).

    Google Scholar 

  17. H. Kato, T. Hirai, I. Tabushi, Y. Kuroda, and H. Okino, Japanese Patent No. 77 106 882; Chem. Abstr., 88, 89730 (1978).

    Google Scholar 

  18. G. R. Newkome and A. T. Nayak, J. Org. Chem., 43, 409 (1978).

    Google Scholar 

  19. G. R. Newkome, S. J. Garbis, and V. K. Majestic, J. Org. Chem., 46, 833 (1981).

    Google Scholar 

  20. G. R. Newkome, A. Nayak, F. Fronczek, T. Kawata, H. C. R. Taylor, L. Maede, and W. Mattice, J. Am. Chem. Soc., 101, 4472 (1979).

    Google Scholar 

  21. G. R. Newkome, A. Nayak, M. G. Sorci, and W. H. Benton, J. Org. Chem., 44, 3812 (1979).

    Google Scholar 

  22. M. Newcomb, J. M. Timko, D. M. Walba, and D. J. Cram, J. Am. Chem. Soc., 99, 6392 (1977).

    Google Scholar 

  23. S. A. Vartanyan, T. R. Akopyan, E. G. Paronikyan, and G. M. Paronikyan, Armyansk. Khim. Zh., 34, 64 (1981).

    Google Scholar 

  24. R. Chenevert and R. Plante, Synthesis, No. 10, 847 (1983).

    Google Scholar 

  25. E. Buhleier, W. Wehner, and F. Vögtle, Chem. Ber., 111, 200 (1978).

    Google Scholar 

  26. E. Buhleier, K. Frensch, F. Luppertz, and F. Vögtle, Ann. Chem., No. 10, 1586 (1978).

    Google Scholar 

  27. M. M. Htay and O. Meth-Cohn, Tetrahedron Lett., No. 1, 79 (1976).

    Google Scholar 

  28. R. J. Hayword, M. M. Htay, and O. Meth-Cohn, Chem. Ind., No. 8, 373 (1977).

    Google Scholar 

  29. L. J. Kaplan, G. R. Weisman, and D. J. Cram, J. Org. Chem., 44, 2226 (1979).

    Google Scholar 

  30. M. M. Htay and O. Meth-Cohn, Tetrahedron Lett., No. 6, 469 (1976).

    Google Scholar 

  31. F. Vögtle and P. Dix, Ann. Chem., No. 10, 1698 (1977).

    Google Scholar 

  32. N. G. Luk'yanenko, A. V. Bogatskii. and Yu. A. Popkov, Khim. Geterotsikl. Soedin., No. 8, 1132 (1981).

    Google Scholar 

  33. N. G. Luk'yanenko, Yu. A. Popkov, and A. V. Bogatskii, Dokl. Akad. Nauk SSSR, 244, 106 (1979).

    Google Scholar 

  34. V. N. Golubev, A. D. Gutsol, A. V. Bogatskii, N. G. Luk'yanenko, T. I. Kirichenko, Yu. A. Popkov, and V. A. Shapkin, Dokl. Akad. Nauk SSSR, 271, 642 (1983).

    Google Scholar 

  35. V. N. Golubev and A. D. Gutsol, élektrokhimiya, 19, 1588 (1983).

    Google Scholar 

  36. A. V. Bogatskii, and N. G. Luk'yanenko, in: Abstracts of Papers and Reports Presented at the 12th Mendeleev Conference on General and Applied Chemistry [in Russian], Vol. 1, Moscow (1981), p. 335.

    Google Scholar 

  37. L. I. Ukhova, A. N. Sergeeva, T. M. Tsvetkova, and G. I. Krivko, in: Summaries of Papers Presented at the 2nd All-Union Conference on the Chemistry of Macrocycles [in Russian], Odessa (1984), p. 20.

  38. N. I. Popov, A. A. Lobanova, Z. A. Dobronravova, and I. G. Kaufman, Zh. Org. Khim., 16, 1551 (1980).

    Google Scholar 

  39. B. Dietrech, T. M. Fyles, J. M. Lehn, L. G. Pease, and D. L. Fyles, Chem. Commun., No. 21, 934 (1978).

    Google Scholar 

  40. A. V. Bogatskii, N. G. Luk'yanenko, and T. I. Kirichenko, Zh. Org. Khim., 16, 1301 (1980).

    Google Scholar 

  41. A. V. Bogat-skii (Bogatsky), N. G. Luk'yanenko (Lukyanenko), and T. I. Kirichenko, Tetrahedron Lett., No. 3, 313 (1980).

    Google Scholar 

  42. O. S. Timofeev, N. G. Luk'yanenko (Lukyanenko), T. I. Kirichenko, V. S. Kalishevich, A. V. Bogatskii,(Bogatsky), A. I. Gren, D. V. Zagorevskii, and Yu. S. Nekrasov, Inorg. Chim. Acta, 77, 245 (1983).

    Google Scholar 

  43. T. I. Kirichenko, A. V. Bogatskii and N. G. Luk'yanenko, Dokl. Akad. Nauk SSSR, 255, 594 (1980).

    Google Scholar 

  44. A. V. Bogatskii (Bogatsky), N. G. Luk'yanenko (Lukyanenko), T. I. Kirichenko, and V. V. Limich, Synthesis, No. 2, 136 (1984).

    Google Scholar 

  45. N. G. Luk'yanenko, A. V. Bogat-skii, T. I. Kirichenko, and S. V. Shcherbakov, Zh. Org. Khim., 17, 1279 (1981).

    Google Scholar 

  46. A. V. Bogatskii,(Bogatsky), N. G. Luk'yanenko (Lukyanenko), and T. I. Kirichenko, Synthesis, No. 6, 464 (1982).

    Google Scholar 

  47. A. V. Bogatskii N. G. Luk'yanenko, T. I. Kirichenko, V. V. Limich, and L. P. Karpenko, Zh. Org. Khim., 20, 101 (1984).

    Google Scholar 

  48. A. V. Bogatskii, Bioorg. Khim., 9, 1445 (1983).

    Google Scholar 

  49. T. E. Lipatova, L. F. Kosyanchuk, and T. S. Khramova, Teor. éksp. Khim., No. 3, 323 (1983).

    Google Scholar 

  50. S. M. Nelson, Pure Appl. Chem., 52, 2461 (1980).

    Google Scholar 

  51. W. Rasshofer, W. M. Müller, and G. Oepen, J. Chem. Res., No. 2, 72 (1978).

    Google Scholar 

  52. H. Gnichtel and C. Graphoff, Ann. Chem., No. 11, 2038 (1983).

    Google Scholar 

  53. I. K. Bhoon and R. P. Singh, J. Inorg. Nucl. Chem., 43, 1685 (1981).

    Google Scholar 

  54. K. K. Abid and D. E. Fenton, Inorg. Chem. Acta, 82, 223 (1984).

    Google Scholar 

  55. S. M. Nelson, F. S. Esho, and M. G. B. Drew, Chem. Commun., No. 8, 388 (1981).

    Google Scholar 

  56. S. M. Nelson, F. S. Esho, A. Lavery, and M. G. B. Drew, J. Am. Chem. Soc., 105, 5693 (1983)

    Google Scholar 

  57. S. M. Nelson, F. S. Esho, and M. G. B. Drew, J. Chem. Soc., Dalton Trans., No. 9, 1857 (1983).

    Google Scholar 

  58. M. G. B. Drew, F. S. Esho, and S. M. Nelson, Inorg. Chim. Acta, 76, 269 (1983).

    Google Scholar 

  59. M. G. B. Drew, F. S. Esho, and S. M. Nelson, Chem. Commun., No. 23, 1347 (1982).

    Google Scholar 

  60. M. G. B. Drew, J. Chem. Soc., Dalton Trans., No. 8, 1653 (1983).

    Google Scholar 

  61. V. M. Dziomko, V. M. Ostrovskaya, and T. E. Zhukova, USSR Inventor's Certificate No. 682517; Byull. Izobret., No. 32 (1979).

  62. V. M. Dziomko, V. M. Ostrovskaya, T. E. Zhukova, and Yu. S. Ryabokobylko, Zh. Obshch. Khim., 51, 2323 (1981).

    Google Scholar 

  63. V. M. Ostrovskaya, I. A. D'yakonova, and T. S. Palilova, USSR Inventor's Certificate No. 105700; Byull. Ozobret., No. 44 (1983).

  64. V. M. Ostrovskaya and I. A. D'yakonova, in: Summaries of Papers Presented at the 2nd All-Union Conference on the Chemistry of Macrocycles [in Russian], Odessa (1984), p. 51.

  65. N. P. Bednyagina, I. Ya. Postovskii, A. D. Garnovskii, and O. A. Osipov, Usp. Khim., 49, 1053 (1975).

    Google Scholar 

  66. I. Ya. Postovskii, I. V. Podgornaya, V. A. Popova, M. I. Ermakova, and O. V. Fedorova, Khim. Geterotsikl. Soedin., No. 11, 1479 (1981).

    Google Scholar 

  67. V. M. Dziomko, V. M. Ostrovskaya, and T. E. Zhukova, Khim. Geterotsikl. Soedin., No. 5, 530 (1979).

    Google Scholar 

  68. Yu. A. Zolotov, N. V. Niz'eva, V. P. Ionov, V. M. Dziomko, V. M. Ostrovskaya, and I. A. D'yakonova, USSR Inventor's Certificate No. 1060200; Byull. Izobr., No. 46 (1983).

  69. N. V. Niz'eva, V. P. Ionov, I. V. Pletnev, D. M. Kumina, V. M. Ostrovskaya, I. A. D'yakova, and Yu. A. Zolotov, Dokl. Akad. Nauk SSSR, 274, 611 (1984).

    Google Scholar 

  70. V. M. Ostrovskaya, I. A. D'yakonova, and T. D. Nikolaeva, in: Summaries of Papers Presented at the 2nd All-Union Confernece on the Chemistry of Macrocycles [in Russian], Odessa (1984), p. 52.

  71. A. V. Sultanov and S. B. Savvin, in: Summaries of Papers Presented at the 2nd All-Union Conference on the Chemistry of Macrocycles [in Russian], Odessa (1984), p. 205.

  72. M. Shiga, M. Takagi, and K. Ueno, Chem. Lett., No. 8, 1021 (1980).

    Google Scholar 

  73. I. V. Podgornaya, Yu. A. Zolotov, V. A. Popova, V. A. Ionov, and O. V. Fedorova, USSR Inventor's Certificate No. 1122657; Byull. Izobr., No. 41 (1984).

  74. M. Kanaoka, A. Isogai, S. Murakoshi, M. Ichinol, A. Suzuki, and S. Tamura, Agric. Biol. Chem., 42, 629 (1978).

    Google Scholar 

  75. A. Isogai, M. Kanaoka, and A. Suzuki, Pept. Chem., 16, 165 (1978); Chem. Abstr., 94, 103802 (1981).

    Google Scholar 

  76. M. Rothe and W. Kreiss, in: Peptides. Proceedings of the European Peptide Symposium (1976), p. 71.

  77. L. A. Fonina, I. S. Savelov (Sawelow), G. G. Avotin' (Avotina), V. T. Ivanov (Ivanow), and Yu. A. Ovchinnikov, in: Peptides. Proceedings of the European Peptide Symposium (1976), p. 636.

  78. L. A. Fonina, G. Ya. Avotin', T. A. Balashova, N. V. Starovoitova, L. B. Senyavina, I. S. Savelov, V. F. Bystrov, V. T. Ivanov, and Yu. A. Ovchinnikov, Bioorg. Khim., 6, 1285 (1980).

    Google Scholar 

  79. J. C. Lagarias, R. A. Houghten, and H. Rapoport, J. Am. Chem. Soc., 100, 8202 (1978).

    Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Additional information

Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 7, pp. 867–882, July, 1987.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Ostrovskaya, V.M., D'yakonova, I.A. Oligooxatetraazacoronands (review). Chem Heterocycl Compd 23, 711–724 (1987). https://doi.org/10.1007/BF00475633

Download citation

  • Received:

  • Issue Date:

  • DOI: https://doi.org/10.1007/BF00475633

Keywords

Navigation