Abstract
The effect of substituents in the furan ring on the dynamics of amidine tautomerism in 1,3-diacetyl-2-(5-R-furfuryl)thioureas is demonstrated. The conformation of 1,3-diacetyl-2-(5-ethoxycarbonylfurfuryl)thiourea was established by x-ray diffraction analysis.
Similar content being viewed by others
Literature Cited
S. Patai (ed.), The Chemistry of Amidines and Imidates, J. Wiley, New York (1975), pp. 1–84.
V. I. Minkin, L. P. Olekhnovich, and Yu. A. Zhdanov, The Molecular Design of Tautomeric Systems [in Russian], Rostovsk. Gosudarstv. Univ., Rostov-on-Don (1977).
O. J. Sherer and P. Hornig, Chem. Ber., 101, 2533 (1967).
V. I. Minkin, L. P. Olekhnovich, Yu. A. Zhdanov, I. E. Mikhailov, V. P. Metlushenko, N. M. Ivanchenko, and N. I. Borisenko, Zh. Org. Khim., 12, 1261 (1976).
V. V. Negrebetskii, A. D. Sinitsa, V. I. Kal'chenko, L. I. Atamas', and L. N. Markovskii, Zh. Obshch. Khim., 53, 343 (1983).
M. I. Kabachnik, Zh. Vsesoyuzn. Khim. Obshchestva, 7, 263 (1962).
G. D. Krapivin, E. B. Usova, and V. G. Kul'nevich, The Chemistry and Technology of Furan Compounds, V. G. Kul'nevich (ed.), Krasnodarsk. Politekhn. Inst., Krasnodar (1987), p. 44.
F. Becker, Z. Naturf., 16b, 236 (1961).
P. Hudson, Acta Cryst., 15, 919 (1962).
A. F. Pozharskii, Theoretical Foundations of the Chemistry of Heterocycles [in Russian], Khimiya, Moscow (1985).
A. Gordon and R. Ford, The Chemist's Guide [Russian translation], Mir, Moscow (1976), p. 129.
R. Gillespie, Molecular Geometry [Russian translation], Mir, Moscow (1975), pp. 31, 32.
E. B. Usova, G. D. Krapivin, V. E. Zavodnik, and V. G. Kul'nevich, Khim. Geterotsikl. Soedin., No. 7, 931 (1990).
G. M. Sheldrick, Computational Crystallography, Oxford University Press, New York-London (1982), p. 506.
E. B. Usova, G. D. Krapivin, and V. G. Kul'nevich, Khim. Geterotsikl. Soedin., No. 4, 557 (1990).
Author information
Authors and Affiliations
Additional information
Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 6, pp. 741–745, June, 1991.
Rights and permissions
About this article
Cite this article
Krapivin, G.D., Usova, E.B., Zavodnik, V.E. et al. Amidine tautomerism in the 1,3-diacyl-2-(5-substituted furfuryl)thiourea series. Molecular structure of 1,3-diacetyl-2-(5-ethoxycarbonylfurfuryl)thiourea. Chem Heterocycl Compd 27, 579–583 (1991). https://doi.org/10.1007/BF00472501
Received:
Revised:
Issue Date:
DOI: https://doi.org/10.1007/BF00472501