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Aromatic N-oxides as 1,3-dipoles and π-donors in reactions with unsaturated compounds. Review

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Chemistry of Heterocyclic Compounds Aims and scope

Abstract

A summary is given for the data on 1,3-dipolar cycloaddition reactions of aromatic N-oxides, which are convenient one-step methods for the synthesis of several heterocyclic compounds. Special attention was given to N-oxides as possible ambident donors in the formation of molecular complexes with dipolarophiles.

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Literature cited

  1. E. Ochiai, J. Org. Chem., 18, 534 (1953).

    Google Scholar 

  2. D. V. Ioffe and L. S. Éfros, Usp. Khim., 30, 1325 (1961).

    Google Scholar 

  3. I. Kuruts, Isomerization of Cyclic Nitrones [in Russian], Chemical Sciences Candidate's Dissertation, Leningrad (1978).

  4. G. Wittig and G. Steinhoff, Ann., 676, 21 (1964).

    Google Scholar 

  5. T. Hisano, K. Harano, T. Matsuoka, T. Suzuki, and Y. Murayama, Chem. Pharm. Bull., 38, 605 (1990).

    Google Scholar 

  6. M. Ungureanu and D. J. Zugravescu, An. Sti. Univ. Jasi, No. 1, 29 (1974).

    Google Scholar 

  7. M. Yoshida, Y. Ishiguro, T. Yamamori, M. Aoyama, T. Endo, H. Noda, K. Funakoshi, S. Saeki, and M. Hamana, Heterocycles, 12, 167 (1979).

    Google Scholar 

  8. Y. Ishiguro, M. Yoshida, K. Funakoshi, S. Saeki, and M. Hamana, Heterocycles, 20, 193 (1983).

    Google Scholar 

  9. R. A. Abramovitch and I. Shinkai, J. Am. Chem. Soc., 96, 5265 (1974).

    Google Scholar 

  10. R. A. Abramovitch, G. Grins, R. B. Rogers, M. J. L. Atwood, M. D. Williams, and S. Grider, J. Org. Chem., 37, 3383 (1972).

    Google Scholar 

  11. H. Seidl and R. Huisgen, Tetrahedron Lett., No. 30, 2023 (1963).

    Google Scholar 

  12. M. Hamana, K. Funakoshi, and Y, Kuchino, Abstracts of Papers of the 90th Annual Meeting of the Pharmaceutical Society of Japan, Sapporo (1970), p. 38.

  13. V. I. Ivanskii, Chemistry of Heterocyclic Compounds [in Russian], Vyssh. Shkola, Moscow (1978), p. 279.

    Google Scholar 

  14. F. A. Mailey and L. R. Ocone, J. Org. Chem., 33, 3343 (1968).

    Google Scholar 

  15. M. Hamana, K. Funakoshi, H. Shigyo, and Y. Kuchino, Chem. Pharm. Bull., 23, 346 (1975).

    Google Scholar 

  16. A. M. Nour El-Din and A.-R. M. Tawfik, J. Chem. Eng. Data, 32, 125 (1987).

    Google Scholar 

  17. A. M. Nour El-Din, A.-R. M. Tawfik, and M. Ramadan, Rev. Roum. Chim., 33, 183 (1988).

    Google Scholar 

  18. Y. Ishiguro, K. Funakoshi, S. Saeki, T. Endo, and M. Hamana, Heterocycles, 20, 158 (1983).

    Google Scholar 

  19. T. Hisano, T. Matsuoka, K. Tsusumi, K. Muraoka, and M. Ichikawa, Chem. Pharm. Bull., 29, 3706 (1981).

    Google Scholar 

  20. M. Hamana, Khim. Geterotsikl. Soedin., No. 9, 1155 (1973).

    Google Scholar 

  21. M. Hamana and M. Yamazaki, Chem. Pharm. Bull., 11, 411 (1963).

    Google Scholar 

  22. T. Hisano, K. Harano, T. Matsuoka, F. Suematsu, and N. Ohizumi, Chem. Pharm. Bull., 33, 1869 (1985).

    Google Scholar 

  23. K. Harano, F. Suematsu, T. Matsuoka, and T. Hisano, Chem. Pharm. Bull., 32, 543 (1984).

    Google Scholar 

  24. T. Matsuoka, M. Shinada, F. Suematsu, K. Harano, and T. Hisano, Chem. Pharm. Bull., 32, 2077 (1984).

    Google Scholar 

  25. T. Matsuoka, K. Harano, H. Kubo, and T. Hisano, Chem. Pharm. Bull., 34, 572 (1986).

    Google Scholar 

  26. K. Harano, R. Kondo, M. Murase, T. Matsuoka, and T. Hisano, Chem. Pharm. Bull., 966 (1986).

  27. T. Hisano, K. Harano, T. Matsuoka, H. Yamada, and M. Kurihara, Chem. Pharm. Bull., 35, 1049 (1987).

    Google Scholar 

  28. A. F. Khlebnikov and R. R. Kostikov, Khim. Geterotsikl. Soedin., No. 6, 856 (1987).

    Google Scholar 

  29. A. Krebs, H. Colberg, U. Hopfner, H. Kimling, and J. Odenthal, Heterocycles, 12, 1153 (1979).

    Google Scholar 

  30. R. A. Abramovitch and I. Shinkai, Accounts Chem. Res., 9, 192 (1976).

    Google Scholar 

  31. H. Noda, T. Yamamori, M. Yoshida, and M. Hamana, Heterocycles, 4, 453 (1976).

    Google Scholar 

  32. Y. Ishiguro, K. Funakoshi, S. Saeki, M. Hamana, I. Ueda, and S. Kawano, Heterocycles, 20, 1545 (1983).

    Google Scholar 

  33. R. M. Acheson, A. S. Bailey, and J. A. Selby, Chem. Commun., No. 20, 2066 (1967).

    Google Scholar 

  34. J. E. Baldwin, R. G. Pudnssery, A. R. Quereshi, and B. Sklarz, J. Am. Chem. Soc., 90, 5325 (1968).

    Google Scholar 

  35. Y. Ishiguro, K. Funakoshi, S. Saeki, M. Hamana, and I. Ueda, Heterocycles, 14, 179 (1980).

    Google Scholar 

  36. R. Huisgen, H. Seidl, and J. Wulff, Chem. Ber., 102, 915 (1961).

    Google Scholar 

  37. S. Takahashi and H. Kano, J. Org. Chem., 30, 1118 (1965).

    Google Scholar 

  38. S. Takahashi and H. Kano, Chem. Pharm. Bull., 14, 1219 (1966).

    Google Scholar 

  39. S. Takahashi and H. Kano, Chem. Pharm. Bull., 16, 527 (1968).

    Google Scholar 

  40. S. R. Challand, C. W. Ress, and R. Storr, Chem. Commun., No. 10, 837 (1973).

    Google Scholar 

  41. A. V. Ryzhakov and L. L. Rodina, Zh. Org. Khim., 25, 1577 (1989).

    Google Scholar 

  42. S. Kano, T. Yokomatsu, Y. Inasha, and S. Shibuya, Heterocycles, 19, 2143 (1982).

    Google Scholar 

  43. R. A. Abramovitch, D. Kishore, M. Konieczny, and Z. Danter, Heterocycles, 25, 13 (1987).

    Google Scholar 

  44. A. M. Nour El-Din, Spectrochim. Acta, 41A, 1101 (1985).

    Google Scholar 

  45. V. S. Troilina, V. N. Sheinker, A. D. Garnovskii, and O. A. Osipov, Zh. Fiz. Khim., 50, 2436 (1976).

    Google Scholar 

  46. A. V. Ryzhakov and L. L. Rodina, Khim. Geterotsikl. Soedin., No. 4, 488 (1991).

    Google Scholar 

  47. A. V. Ryzhakov, Reactions of Aromatic N-Oxides and Ethylene System π-Systems [in Russian], Chemical Sciences Candidate's Dissertation, Leningrad (1990).

  48. T. V. Bezdvornykh and A. V. Ryzhakov, Abstracts of the All-Union Conference on the Electronics of Organic Materials [in Russian], Dombai (1990), p. 123.

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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 5, pp. 579–591, May, 1992

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Ryzhakov, A.V., Rodina, L.L. Aromatic N-oxides as 1,3-dipoles and π-donors in reactions with unsaturated compounds. Review. Chem Heterocycl Compd 28, 483–493 (1992). https://doi.org/10.1007/BF00475241

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  • DOI: https://doi.org/10.1007/BF00475241

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