Chemistry of Heterocyclic Compounds

, Volume 34, Issue 1, pp 1–12 | Cite as

Hydroxymethylation and alkylation of compounds of the furan, thiophene, and pyrrole series in the presence of H+ cations (review)

  • I. G. Iovel'
  • E. Lukevics


Published data and the results of the authors' own investigations on the transformations of O-, S-, and N-heterocyclic compounds under the conditions of acid-catalyzed hydroxymethylation and alkylation are summarized. The mechanisms and the directions of the reactions taking place under the influence of weakly and strongly acidic ion exchangers are discussed.


Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.


  1. 1.
    T. L. Cairns, B. C. McKusick, and V. Weinmayr, J. Am. Chem. Soc.,73, 1270 (1951).Google Scholar
  2. 2.
    L. L. J. Fauque, US Patent No. 2,681,917; Chem. Abstr.,49, 7600 (1955).Google Scholar
  3. 3.
    W. H. Brown and H. Sawatzky, Can. J. Chem.,34, 1147 (1956).Google Scholar
  4. 4.
    L. Rigal, A. Gaset, and J. P. Gorrichon, Ind. Eng. Chem. Prod. Res. Dev.,20, 719 (1981).Google Scholar
  5. 5.
    N. G. Polyanskii, Catalysis by Ion Exchangers [in Russian], Khimiya, Moscow (1973).Google Scholar
  6. 6.
    V. I. Isagulyants, Ion-Exchange Catalysis [in Russian], Izd. Akad. Nauk Arm. SSR, Erevan (1975).Google Scholar
  7. 7.
    G. M. Coppola, Synthesis, No. 12, 1021 (1984).Google Scholar
  8. 8.
    C. Malanga, Chem. Ind., No. 24, 856 (1987).Google Scholar
  9. 9.
    M. Petrini, R. Ballini, and E. Markantoni, Synth. Commun.,18, 847 (1988).Google Scholar
  10. 10.
    R. Ballini and M. Petrini, J. Chem. Soc. Trans. Perkin I, No. 9, 2563 (1988).Google Scholar
  11. 11.
    A. Mitschker, R. Waganer, and P. M. Lange, Heterogeneous Catalysis and Fine Chemicals, First International Symposium, Poitiers, France (1988), p. 145.Google Scholar
  12. 12.
    V. I. Isagulyants, T. G. Khaimova, V. R. Melikyan, and S. V. Pokrovskaya, Usp. Khim.,37, 61 (1988).Google Scholar
  13. 13.
    M. Delmas, P. Kalck, J. P. Gorrichon, and A. Gaset, J. Mol. Cat.,4, 443 (1978).Google Scholar
  14. 14.
    M. Delmas and A. Gaset, Tetrahedron Lett.,22, 723 (1981).Google Scholar
  15. 15.
    K. A. Kasymova, V. Z. Sharf, E. F. Litvin, and E. N. Grigor'eva, Izv. Akad. Nauk SSSR. Ser. Khim., No. 1, 224 (1987).Google Scholar
  16. 16.
    I. G. Iovel', Yu. S. Gol'dberg, and M. V. Shimanskaya, Fifth International Symposium “Relation Between Homogeneous and Heterogeneous Catalysis,” Abstracts [in Russian], Novosibirsk (1986), p. 101.Google Scholar
  17. 17.
    Yu. Goldberg, I. Iovel, E. Abele, and M. Shymanska, Sixth International Conference on Organic Synthesis: Program and Abstracts of Papers, Moscow (1986), p. 65.Google Scholar
  18. 18.
    I. Iovel, Yu. Goldberg, and M. Shymanska, Ninth Symposium on the Chemistry of Heterocyclic Compounds. Abstracts of Papers, Bratislava (1987), p. 173.Google Scholar
  19. 19.
    I. G. Iovel, Yu. Sh. Goldberg, and M. V. Shymanska, J. Mol. Catal.,57, 91 (1989).Google Scholar
  20. 20.
    I. G. Iovel', Yu. Sh. Gol'dberg, and M. V. Shimanskaya, Khim. Geterotsikl. Soedin., No. 12, 1640 (1991).Google Scholar
  21. 21.
    É. Lukevits, L. M. Ignatovich, Yu. Sh. Gol'dberg, and M. V. Shimanskaya, Khim. Geterotsikl. Soedin., No. 6, 853 (1986).Google Scholar
  22. 22.
    I. G. Iovel, Yu. Sh. Goldberg, M. V. Shymanska, and E. Lukevics, Synth. Commun.,18, 1261 (1988).Google Scholar
  23. 23.
    I. G. Iovel', Yu. Sh. Gol'dberg, and M. V. Shimanskaya, Khim. Geterotsikl. Soedin., No. 6, 746 (1989).Google Scholar
  24. 24.
    I. Iovel', M. Fleisher, Yu. Popelis, M. Shimanska, and E. Lukevics, Khim. Geterotsikl. Soedin., No. 2, 163 (1995).Google Scholar
  25. 25.
    Fluka Catalog. 14. Biochemical Reagents, Fluka AG, Buchs, Switzerland (1984), p. 93.Google Scholar
  26. 26.
    A. A. Lur'e, Chromatographic Materials [in Russian], Khimiya, Moscow (1978).Google Scholar
  27. 27.
    P. Rys and W. J. Steinegger, J. Am. Chem. Soc.,101, 4801 (1979).Google Scholar
  28. 28.
    E. M. Arnett, R. A. Haaksma, B. Chawla, and M. H. Healy, J. Am. Chem. Soc.,108, 4888 (1986).Google Scholar
  29. 29.
    A. L. Mndzhoyan, B. G. Afrikyan, M. G. Grigoryan, and É. A. Markaryan, Dokl. Akad. Nauk Arm. SSSR,25, 277 (1957).Google Scholar
  30. 30.
    V. M. Mičovič, R. I. Mamizič, D. Jeremič, and M. Lj. Mihailovič, Tetrahedron,20, 2279 (1964).Google Scholar
  31. 31.
    Yu. L. Kuz'min, V. M. Ignat'ev, G. S. Gurevich, V. V. Golovin, S. A. Fedotova, M. S. Borts, B. M. Levitin, and A. N. Karpov, Byull. Izobret., No. 10, 105 (1983).Google Scholar
  32. 32.
    R. D. Tiwari and N. P. Srivastava, Rec. Trav. Chim. Pays Bas,75, 254 (1956).Google Scholar
  33. 33.
    Organic Syntheses [Russian translation], Vol. 2, IL, Moscow (1949), p. 219.Google Scholar
  34. 34.
    I. Matsumoto, K. Nakagawa, and K. Horiuchi, Japanese Patent No. 7,340,463; Chem. Abstr.,79, 66157 (1973).Google Scholar
  35. 35.
    J. M. Timko and D. J. Cram, J. Am. Chem. Soc.,96, 7159 (1974).Google Scholar
  36. 36.
    N. K. Moshchinskaya and V. P. Sorokin, Inventor's Certificate No. 176,919; Byul. Izobret., No. 24, 25 (1965).Google Scholar
  37. 37.
    N. N. Shmagina, A. I. Kurasheva, and V. I. Fedotova, Methods for the Production of Chemical Reagents and Products [in Russian], No. 20, Moscow (1969), p. 90.Google Scholar
  38. 38.
    V. A. Smirnov, V. G. Kulnevich, G. N. Solovets, and D. P. Semchenko, US Patent No. 3,847,452; Chem. Abstr.,83, 58640 (1975).Google Scholar
  39. 39.
    J. F. Walker, Formaldehyde (third ed.), Pergamon, New York (1964).Google Scholar
  40. 40.
    J. G. Berger and K. Schoen, J. Heterocycl. Chem.,9, 419 (1972).Google Scholar
  41. 41.
    S. H. Patinkin and B. S. Friedman, Friedel-Crafts and Related Reactions, G. A. Olah (ed.), Vol. 2, Interscience, New York (1964), p. 104.Google Scholar
  42. 42.
    C. Price, Organic Reactions [Russian translation], K. A. Kochenshkov (ed.), IL, Moscow (1951), p. 7.Google Scholar
  43. 43.
    J. E. Fitzpatrick, D. J. Milner, and P. White, Synth. Commun.,12, 489 (1982).Google Scholar
  44. 44.
    Y. Kamitori, M. Hojo, R. Masuda, T. Izumi, and Sh. Tsukamoto, J. Org. Chem.,49, 4161 (1984).Google Scholar
  45. 45.
    L. I. Belen'kii, A. P. Yakubov, and I. A. Bessonova, Zh. Org. Khim.,13, 364 (1977).Google Scholar
  46. 46.
    L. I. Belen'kii and A. P. Yakubov, Tetrahedron,40, 2471 (1984).Google Scholar
  47. 47.
    P. S. Skel and G. P. Bean, J. Am. Chem. Soc.,84, 4655 (1962).Google Scholar
  48. 48.
    P. B. Gerritt, J. Org. Chem.,32, 229 (1967).Google Scholar
  49. 49.
    R. Nicoletti and C. Germani, Ric. Sci.,36, 1343 (1966); Chem. Abstr.,67, 43619 (1967).Google Scholar
  50. 50.
    J. K. Groves, H. J. Anderson, and H. Nagy, Can. J. Chem.,49, 2427 (1971).Google Scholar
  51. 51.
    A. F. Pozharskii, Theoretical Principles of the Chemistry of Heterocycles [in Russian], Khimiya, Moscow (1985).Google Scholar
  52. 52.
    Ya. L. Gol'dfarb and Ya. L. Danyushevskii, Izv. Akad. Nauk. SSSR. Ser. Khim., No. 3, 540 (1963).Google Scholar
  53. 53.
    T. S. Gardner, E. Winis, and J. Lee, J. Org. Chem.,23, 823 (1958).Google Scholar
  54. 54.
    Ya. L. Gol'dfarb and Ya. L. Danyushevskii, Zh. Obshch. Khim.,31, 3654 (1961).Google Scholar
  55. 55.
    P. S. Clezy and W. Diakiw, Aust. J. Chem.,24, 2665 (1971).Google Scholar

Copyright information

© Plenum Publishing Corporation 1998

Authors and Affiliations

  • I. G. Iovel'
  • E. Lukevics

There are no affiliations available

Personalised recommendations