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1,2-Dioximes in the trofimov reaction

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Chemistry of Heterocyclic Compounds Aims and scope

Abstract

3,3′-Dimethyl-1,1′-divinyl-2,2′-dipyrrole was obtained during the reaction of 3,4-hexanedione dioximes with acetylene under pressure in the potassium hydroxide-DMSO system. In the case of 1,2-cyclohexanedione dioxime 2,2′-dipyrrole and 2-pyridyl-and 2-acylpyrroles were isolated. α-Benzil and α-furil dioximes give 3,4-diphenyl-and 3,4-di(2-furyl)-1,2,5-oxadiazoles respectively in addition to their mono-and divinyl derivatives.

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References

  1. D. L. Boger and M. Patel, J. Org. Chem., 53, 1405 (1988).

    CAS  Google Scholar 

  2. A. Nakamura, K. Nagai, K. Ando, and G. Tamura, J. Antibiot., 39, 1155 (1985).

    Google Scholar 

  3. J. L. Sessler and A. K. Burrell, Top. Curr. Chem., 161, 177 (1991).

    Google Scholar 

  4. C.-M. Che, C.-W. Wan, W.-Z. Lin, W.-Y. Yu, Z.-Y. Zhou, W.-Y. Lai, and S.-T. Lee, Chem. Commun., 721 (2001).

  5. R. Grigg and A. W. Johnson, J. Chem. Soc., 3315 (1964).

  6. J. L. Sessler, M. Cyr, and A. K. Burrell, Tetrahedron, 48, 9661 (1992).

    Article  CAS  Google Scholar 

  7. H. Bauer, Chem. Ber., 101, 1286 (1968).

    CAS  Google Scholar 

  8. T. Itahara, J. Chem. Soc. Chem. Commun., 49 (1980).

  9. H. Falk and H. Flödl, Monatsch. Chem., 119, 247 (1988).

    CAS  Google Scholar 

  10. W. Hinz, R. A. Jones, S. U. Patel, and M.-H. Karatza, Tetrahedron, 42, 3753 (1986).

    Article  CAS  Google Scholar 

  11. H. Rapoport and J. Bordner, J. Org. Chem., 29, 2727 (1964).

    CAS  Google Scholar 

  12. J. Bordner and H. Rapoport, J. Org. Chem., 30, 3824 (1965).

    Google Scholar 

  13. A. M. Vasil’tsov, A. B. Zaitsev, E. Yu. Schmidt, A. I. Mikhaleva, and A. V. Afonin, Mendeleev Commun., 74 (2001).

  14. R. J. Tedeschi, in: Encyclopedia of Physical Science and Technology,Academic Press, San Diego (1992), Vol. 1, p. 27.

    Google Scholar 

  15. G. P. Bean, in: R. A. Jones (editor), Pyrroles, Part 1, Wiley, New York (1992), p. 105.

    Google Scholar 

  16. B. A. Trofimov, in: R. A. Jones (editor), Pyrroles, Part 1, Wiley, New York (1992), p. 131.

    Google Scholar 

  17. B. A. Trofimov, in: A. R. Katritzky (editor) Adv. Heterocycl. Chem., Academic Press, San Diego (1990), Vol. 51, p. 177.

    Google Scholar 

  18. B. A. Trofimov and A. I. Mikhaleva, N-Vinylpyrroles [in Russian], (1984).

  19. B. A. Trofimov, A. I. Mikhaleva, A. M. Vasil’tsov, E. Yu. Schmidt, O. A. Tarasova, L. V. Morozova, L. N. Sobenina, Th. Preiss, and J. Henkelmann, Synthesis, 1125 (2000).

  20. B. A. Trofimov, E. Yu. Schmidt, A. M. Vasil’tsov, A. I. Mikhaleva, A. B. Zaitsev, L. V. Morozova, A. G. Gorshkov, J.-D. Arndt, and J. Henkelmann, Synthesis, 2427 (2001).

  21. S. E. Korostova, S. G. Shevchenko, M. V. Sigalov, and N. I. Golovanova, Khim. Geterotsikl. Soedin., 460 (1991).

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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 1, pp. 39–46, January, 2006.

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Zaitsev, A.B., Schmidt, E.Y., Vasil’tsov, A.M. et al. 1,2-Dioximes in the trofimov reaction. Chem Heterocycl Compd 42, 34–41 (2006). https://doi.org/10.1007/s10593-006-0043-0

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