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Directed synthesis of semicarbazones, thiosemicarbazones, and guanylhydrazones of 1-vinylpyrrole-2-carbaldehydes

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Chemistry of Heterocyclic Compounds Aims and scope

Previously unknown 1-vinylpyrrole semicarbazones, thiosemicarbazones, and guanylhydrazones have been obtained in 68.0–90.5% yield by the reaction of 1-vinylpyrrole-2-carbaldehydes with semicarbazide, thiosemicarbazide, and aminoguanidine.

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References

  1. V. N. Elokhina, A. E. Aleksandrova, A. S. Nakhmanovich, R. A. Shcheglova, Z. V. Karnaukhova, T. I. Vinogradova, and I. D. Kalikhman, Russian Patent 1621449 (1993); Chem. Abs., 126, 312253 (1997).

    Google Scholar 

  2. A. Castiñeiras, R. Carballo, and T. Pérez, Polyhedron, 20, 441 (2001).

    Article  Google Scholar 

  3. Lefevre-Groboillot, S. Dijols, J.-L. Boucher, J.-P. Mahy, R. Ricoux, A. Desbois, J.-L. Zimmermann, and D. Mansuy, Biochemistry, 40, 9909 (2001).

    Article  CAS  Google Scholar 

  4. X. Du, C. Guo, E. Hansell, P. S. Doyle, C. R. Caffrey, T. P. Holler, J. H. McKerrow, and F. E. Cohen, J. Med. Chem., 45, 2695 (2002).

    Article  CAS  Google Scholar 

  5. S. Fukumoto, E. Imamiya, K. Kusumoto, S. Fujiwara, T. Watanabe, and M. Shiraishi, J. Med. Chem., 45, 3009 (2002).

    Article  CAS  Google Scholar 

  6. T. S. Lobana, Rekha, and R. J. Butcher, Trans. Metal Chem., 29, 291 (2004).

    Article  CAS  Google Scholar 

  7. A. G. Quiroga and C. N. Ranninger, Coord. Chem. Rev., 248, 119 (2004).

    Article  CAS  Google Scholar 

  8. A. Andreani, M. Granaiola, A. Leoni, A. Locatelli, R. Morigi, M. Rambaldi, G. Lenaz, R. Fato, C. Bergamini, and G. Farruggia, J. Med. Chem., 48, 3085 (2005).

    Article  CAS  Google Scholar 

  9. T. S. Zatsepin, D. A. Stetsenko, M. J. Gait, and T. S. Oretskaya, Bioconjugate Chem., 16, 471 (2005).

    Article  CAS  Google Scholar 

  10. D. Sriram, P. Yogeeswari, R. Thirumurugan, and R. K. Pavana, J. Med. Chem., 49, 3448 (2006).

    Article  CAS  Google Scholar 

  11. T. S. Lobana, Rekha, R. J. Butcher, A. Castineiras, E. Bermejo, and P. V. Bharatam, Inorg. Chem., 45, 1535 (2006).

    Article  CAS  Google Scholar 

  12. E. López-Torres and U. Abram, Inorg. Chem., 47, 2890 (2008).

    Article  Google Scholar 

  13. T. S. Lobana, A. Sánchez, J. S. Casas, A. Castiñeiras, J. Sordo, M. S. Garcia-Tasende, and E. M. Vázquez-López, J. Chem. Soc., Dalton Trans., 4289 (1997).

  14. A. I. Mikhaleva, A. B. Zaitsev, A. V. Ivanov, E. Yu. Schmidt, A. M. Vasil'tsov, and B. A. Trofimov, Tetrahedron Lett., 47, 3693 (2006).

    Article  CAS  Google Scholar 

  15. A. M. Vasil'tsov, A. V. Ivanov, I. A. Ushakov, A. I. Mikhaleva, and B. A. Trofimov, Synthesis, 452 (2007).

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

    Google Scholar 

  17. I. Guben, Methods of Organic Chemistry [in Russian], Vol. 3, Glavkhimlit, Moscow (1935), Pt. 2, p. 64.

    Google Scholar 

  18. Veigand-Hilgetag, Experimental Methods in Organic Chemistry [in Russian], Khimiya, Moscow (1976), p. 477.

    Google Scholar 

  19. L. Hammett, Fundamentals of Physical Organic Chemistry [Russian translation], Mir, Moscow (1972), p. 452.

    Google Scholar 

  20. G. J. Karabatsos and R. A. Taller, Tetrahedron, 24, 3347 (1968).

    Article  CAS  Google Scholar 

  21. P. E. Hansen, Prog. NMR Spectrosc., 4, 175 (1981).

    Article  Google Scholar 

  22. A. J. Gordon and R. A. Ford, Chemist's Companion, Handbook of Practical Data, Techniques and References, Wiley-Interscience, New York (1972), 560 pp.

    Google Scholar 

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Correspondence to A. I. Mikhaleva.

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Dedicated to Academician B. A. Trofimov on his 70th jubilee.

Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 9, pp. 1384–1390, September, 2008.

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Mikhaleva, A.I., Ivanov, A.V., Vasil’tsov, A.M. et al. Directed synthesis of semicarbazones, thiosemicarbazones, and guanylhydrazones of 1-vinylpyrrole-2-carbaldehydes. Chem Heterocycl Comp 44, 1117–1122 (2008). https://doi.org/10.1007/s10593-008-0162-x

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  • DOI: https://doi.org/10.1007/s10593-008-0162-x

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