Skip to main content
Log in

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

  • Published:
Chemistry of Heterocyclic Compounds Aims and scope

Abstract

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.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Similar content being viewed by others

References

  1. T. L. Cairns, B. C. McKusick, and V. Weinmayr, J. Am. Chem. Soc.,73, 1270 (1951).

    Google Scholar 

  2. L. L. J. Fauque, US Patent No. 2,681,917; Chem. Abstr.,49, 7600 (1955).

    Google Scholar 

  3. W. H. Brown and H. Sawatzky, Can. J. Chem.,34, 1147 (1956).

    Google Scholar 

  4. L. Rigal, A. Gaset, and J. P. Gorrichon, Ind. Eng. Chem. Prod. Res. Dev.,20, 719 (1981).

    Google Scholar 

  5. N. G. Polyanskii, Catalysis by Ion Exchangers [in Russian], Khimiya, Moscow (1973).

    Google Scholar 

  6. V. I. Isagulyants, Ion-Exchange Catalysis [in Russian], Izd. Akad. Nauk Arm. SSR, Erevan (1975).

    Google Scholar 

  7. G. M. Coppola, Synthesis, No. 12, 1021 (1984).

    Google Scholar 

  8. C. Malanga, Chem. Ind., No. 24, 856 (1987).

    Google Scholar 

  9. M. Petrini, R. Ballini, and E. Markantoni, Synth. Commun.,18, 847 (1988).

    Google Scholar 

  10. R. Ballini and M. Petrini, J. Chem. Soc. Trans. Perkin I, No. 9, 2563 (1988).

    Google Scholar 

  11. A. Mitschker, R. Waganer, and P. M. Lange, Heterogeneous Catalysis and Fine Chemicals, First International Symposium, Poitiers, France (1988), p. 145.

  12. V. I. Isagulyants, T. G. Khaimova, V. R. Melikyan, and S. V. Pokrovskaya, Usp. Khim.,37, 61 (1988).

    Google Scholar 

  13. M. Delmas, P. Kalck, J. P. Gorrichon, and A. Gaset, J. Mol. Cat.,4, 443 (1978).

    Google Scholar 

  14. M. Delmas and A. Gaset, Tetrahedron Lett.,22, 723 (1981).

    Google Scholar 

  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. 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.

  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.

  18. I. Iovel, Yu. Goldberg, and M. Shymanska, Ninth Symposium on the Chemistry of Heterocyclic Compounds. Abstracts of Papers, Bratislava (1987), p. 173.

  19. I. G. Iovel, Yu. Sh. Goldberg, and M. V. Shymanska, J. Mol. Catal.,57, 91 (1989).

    Google Scholar 

  20. I. G. Iovel', Yu. Sh. Gol'dberg, and M. V. Shimanskaya, Khim. Geterotsikl. Soedin., No. 12, 1640 (1991).

    Google Scholar 

  21. É. Lukevits, L. M. Ignatovich, Yu. Sh. Gol'dberg, and M. V. Shimanskaya, Khim. Geterotsikl. Soedin., No. 6, 853 (1986).

    Google Scholar 

  22. I. G. Iovel, Yu. Sh. Goldberg, M. V. Shymanska, and E. Lukevics, Synth. Commun.,18, 1261 (1988).

    Google Scholar 

  23. I. G. Iovel', Yu. Sh. Gol'dberg, and M. V. Shimanskaya, Khim. Geterotsikl. Soedin., No. 6, 746 (1989).

    Google Scholar 

  24. I. Iovel', M. Fleisher, Yu. Popelis, M. Shimanska, and E. Lukevics, Khim. Geterotsikl. Soedin., No. 2, 163 (1995).

    Google Scholar 

  25. Fluka Catalog. 14. Biochemical Reagents, Fluka AG, Buchs, Switzerland (1984), p. 93.

  26. A. A. Lur'e, Chromatographic Materials [in Russian], Khimiya, Moscow (1978).

    Google Scholar 

  27. P. Rys and W. J. Steinegger, J. Am. Chem. Soc.,101, 4801 (1979).

    Google Scholar 

  28. E. M. Arnett, R. A. Haaksma, B. Chawla, and M. H. Healy, J. Am. Chem. Soc.,108, 4888 (1986).

    Google Scholar 

  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. V. M. Mičovič, R. I. Mamizič, D. Jeremič, and M. Lj. Mihailovič, Tetrahedron,20, 2279 (1964).

    Google Scholar 

  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. R. D. Tiwari and N. P. Srivastava, Rec. Trav. Chim. Pays Bas,75, 254 (1956).

    Google Scholar 

  33. Organic Syntheses [Russian translation], Vol. 2, IL, Moscow (1949), p. 219.

  34. I. Matsumoto, K. Nakagawa, and K. Horiuchi, Japanese Patent No. 7,340,463; Chem. Abstr.,79, 66157 (1973).

    Google Scholar 

  35. J. M. Timko and D. J. Cram, J. Am. Chem. Soc.,96, 7159 (1974).

    Google Scholar 

  36. N. K. Moshchinskaya and V. P. Sorokin, Inventor's Certificate No. 176,919; Byul. Izobret., No. 24, 25 (1965).

    Google Scholar 

  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. 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. J. F. Walker, Formaldehyde (third ed.), Pergamon, New York (1964).

    Google Scholar 

  40. J. G. Berger and K. Schoen, J. Heterocycl. Chem.,9, 419 (1972).

    Google Scholar 

  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. C. Price, Organic Reactions [Russian translation], K. A. Kochenshkov (ed.), IL, Moscow (1951), p. 7.

    Google Scholar 

  43. J. E. Fitzpatrick, D. J. Milner, and P. White, Synth. Commun.,12, 489 (1982).

    Google Scholar 

  44. Y. Kamitori, M. Hojo, R. Masuda, T. Izumi, and Sh. Tsukamoto, J. Org. Chem.,49, 4161 (1984).

    Google Scholar 

  45. L. I. Belen'kii, A. P. Yakubov, and I. A. Bessonova, Zh. Org. Khim.,13, 364 (1977).

    Google Scholar 

  46. L. I. Belen'kii and A. P. Yakubov, Tetrahedron,40, 2471 (1984).

    Google Scholar 

  47. P. S. Skel and G. P. Bean, J. Am. Chem. Soc.,84, 4655 (1962).

    Google Scholar 

  48. P. B. Gerritt, J. Org. Chem.,32, 229 (1967).

    Google Scholar 

  49. R. Nicoletti and C. Germani, Ric. Sci.,36, 1343 (1966); Chem. Abstr.,67, 43619 (1967).

    Google Scholar 

  50. J. K. Groves, H. J. Anderson, and H. Nagy, Can. J. Chem.,49, 2427 (1971).

    Google Scholar 

  51. A. F. Pozharskii, Theoretical Principles of the Chemistry of Heterocycles [in Russian], Khimiya, Moscow (1985).

    Google Scholar 

  52. Ya. L. Gol'dfarb and Ya. L. Danyushevskii, Izv. Akad. Nauk. SSSR. Ser. Khim., No. 3, 540 (1963).

    Google Scholar 

  53. T. S. Gardner, E. Winis, and J. Lee, J. Org. Chem.,23, 823 (1958).

    Google Scholar 

  54. Ya. L. Gol'dfarb and Ya. L. Danyushevskii, Zh. Obshch. Khim.,31, 3654 (1961).

    Google Scholar 

  55. P. S. Clezy and W. Diakiw, Aust. J. Chem.,24, 2665 (1971).

    Google Scholar 

Download references

Authors

Additional information

The authors consider it their duty to mention that the work on the review was initiated by Prof. M. V. Shimanskaya.

Latvian Institute of Organic Synthesis, Riga. Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 1, pp. 3–16, January, 1998.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Iovel', I.G., Lukevics, E. Hydroxymethylation and alkylation of compounds of the furan, thiophene, and pyrrole series in the presence of H+ cations (review). Chem Heterocycl Compd 34, 1–12 (1998). https://doi.org/10.1007/BF02290607

Download citation

  • Received:

  • Issue Date:

  • DOI: https://doi.org/10.1007/BF02290607

Keywords

Navigation