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.
Similar content being viewed by others
References
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).
A. Castiñeiras, R. Carballo, and T. Pérez, Polyhedron, 20, 441 (2001).
Lefevre-Groboillot, S. Dijols, J.-L. Boucher, J.-P. Mahy, R. Ricoux, A. Desbois, J.-L. Zimmermann, and D. Mansuy, Biochemistry, 40, 9909 (2001).
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).
S. Fukumoto, E. Imamiya, K. Kusumoto, S. Fujiwara, T. Watanabe, and M. Shiraishi, J. Med. Chem., 45, 3009 (2002).
T. S. Lobana, Rekha, and R. J. Butcher, Trans. Metal Chem., 29, 291 (2004).
A. G. Quiroga and C. N. Ranninger, Coord. Chem. Rev., 248, 119 (2004).
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).
T. S. Zatsepin, D. A. Stetsenko, M. J. Gait, and T. S. Oretskaya, Bioconjugate Chem., 16, 471 (2005).
D. Sriram, P. Yogeeswari, R. Thirumurugan, and R. K. Pavana, J. Med. Chem., 49, 3448 (2006).
T. S. Lobana, Rekha, R. J. Butcher, A. Castineiras, E. Bermejo, and P. V. Bharatam, Inorg. Chem., 45, 1535 (2006).
E. López-Torres and U. Abram, Inorg. Chem., 47, 2890 (2008).
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).
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).
A. M. Vasil'tsov, A. V. Ivanov, I. A. Ushakov, A. I. Mikhaleva, and B. A. Trofimov, Synthesis, 452 (2007).
B. A. Trofimov and A. I. Mikhaleva, N-Vinylpyrroles [in Russian], Nauka, Novosibirsk, (1984).
I. Guben, Methods of Organic Chemistry [in Russian], Vol. 3, Glavkhimlit, Moscow (1935), Pt. 2, p. 64.
Veigand-Hilgetag, Experimental Methods in Organic Chemistry [in Russian], Khimiya, Moscow (1976), p. 477.
L. Hammett, Fundamentals of Physical Organic Chemistry [Russian translation], Mir, Moscow (1972), p. 452.
G. J. Karabatsos and R. A. Taller, Tetrahedron, 24, 3347 (1968).
P. E. Hansen, Prog. NMR Spectrosc., 4, 175 (1981).
A. J. Gordon and R. A. Ford, Chemist's Companion, Handbook of Practical Data, Techniques and References, Wiley-Interscience, New York (1972), 560 pp.
Author information
Authors and Affiliations
Corresponding author
Additional information
Dedicated to Academician B. A. Trofimov on his 70th jubilee.
Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 9, pp. 1384–1390, September, 2008.
Rights and permissions
About this article
Cite this article
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
Received:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s10593-008-0162-x