Chemistry of Heterocyclic Compounds

, Volume 35, Issue 1, pp 23–32 | Cite as

2(5H)-furanone in the vilsmeier—haak reaction. Synthesis of β-substituted furans. Molecular structures of 3-dimethylaminomethylene-5-formyl-2(3H)-furanone and dimethylammonium 3,5-di(2,2-dimethyl-4,6-dioxo-1,3-dioxan-5-ylidenemethyl)-2-furanolate

  • G. D. Krapivin
  • N. D. Kozhina
  • L. A. Chernousenko
  • V. E. Zavodnik


The reaction of 2(5H)-furanone with the Vilsmeier-Haak-Arnold reagent and subsequent addition of concentrated aqueous HClO4 to the reaction mixture give (3-dimethylaminomethylen-2-oxo-3H-5-furanyl)methylenimmonium perchlorate, whose hydrolysis under various conditions leads to 3-dimethylaminomethylene-5-formyl-2(3H)-furanone or to the potassium salt of 5-hydroxy-2,4-furandicarbaldehyde. The reaction of these products with CH-acids was studied. The structures of the key compounds of this work have been proved by the method of X-ray diffraction analysis.


Potassium Hydrolysis Organic Chemistry Molecular Structure Diffraction Analysis 
These keywords were added by machine and not by the authors. This process is experimental and the keywords may be updated as the learning algorithm improves.


Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.


  1. 1.
    N. D. Kozhina, G. D. Krapivin, V. E. Zavodnik, T. Gratsza, D. Vegh, L. A. Chernousenko, and L. A. Badovskaya, Khim. Geterotsikl. Soedin., No. 1, 135 (1995).Google Scholar
  2. 2.
    L. N. Sorotskaya, L. A. Badovskaya, T. Ya. Kaklyugina, L. I. Belen'kii, A. V. Ignatenko, A. Krutoshikova, and L. A. Pantseva, Zh. Org. Khim.,25, 175 (1989).Google Scholar
  3. 3.
    G. F. Muzychenko, V. G. Glukhovtsev, L. A. Badovskaya, N. D. Kozhina, A. V. Ignatenko, O. B. Kravchenko, and G. I. Nikitin, Zh. Org. Khim.,17, 481 (1981).Google Scholar
  4. 4.
    E. Yoshii, N. Koizumi, and E. Kitatsuji, Heterocycles,4, 1663 (1976).Google Scholar
  5. 5.
    A. Vilsmeier and A. Haak, Ber.,60, 121 (1927).Google Scholar
  6. 6.
    M. A. Kira, Z. M. Nofal, and K. Z. Gadolla, Tetrahedron Lett., No. 48, 4215 (1970).Google Scholar
  7. 7.
    K. Kiyomi and M. Ichino, J. Org. Chem.,37, 284 (1972).Google Scholar
  8. 8.
    A. I. Kitaigorodskii, P. M. Zorkii and V. K. Bel'skii, Structure of Organic Compounds (Structural Data 1971–1973) [in Russian], Nauka, Moscow (1982).Google Scholar
  9. 9.
    G. D. Krapivin, N. I. Val'ter, V. E. Zavodnik, T. Ya. Kaklyugina, and V. G. Kul'nevich, Khim. Geterotsikl. Soedin., No. 3, 335 (1994).Google Scholar
  10. 10.
    A. Gordon and R. Ford, Chemist's Handbook [Russian translation], Mir, Moscow (1976), p. 129.Google Scholar
  11. 11.
    K. A. Coulson, Theoretical Organic Chemistry. Reports Presented at the Kekule Symposium Organized by the Chemical Society, London September, 1958 [Russian translation], Moscow (1963), p. 66.Google Scholar
  12. 12.
    G. D. Krapivin, N. I. Val'ter, V. E. Zavodnik, V. E. Bel'skii, and V. G. Kul'nevich, Khim. Geterotsikl. Soedin., No. 11, 1453 (1988).Google Scholar
  13. 13.
    G. D. Krapivin, N. I. Val'ter, V. E. Zavodnik, D. Vegh, L. Fishera, and V. G. Kul'nevich, Khim. Geterotsikl. Soedin., No. 7, 899 (1995).Google Scholar
  14. 14.
    A. I. Kiprianov, Usp. Khim.,11, 1283 (1971).Google Scholar
  15. 15.
    G. M. Sheldrick, Computational Crystallography, Oxford Univ. Press, New York-Oxford (1982), p. 506.Google Scholar

Copyright information

© Kluwer Academic/Plenum 1999

Authors and Affiliations

  • G. D. Krapivin
  • N. D. Kozhina
  • L. A. Chernousenko
  • V. E. Zavodnik

There are no affiliations available

Personalised recommendations