Skip to main content
Log in

Studies in the imidazole series

LVIII. Debenzylation of n-benzyl-substituted 1H-pyrrolo[1,2-a]imidazoles and 4H-pyrrolo[1,2-a]benzimidazoles

  • Published:
Chemistry of Heterocyclic Compounds Aims and scope

Abstract

The debenzylation of N-benzyl-substituted 1H-pyrrolo[1,2-a]imidazoles and 4H-pyrrolo-[1,2-a]benzimidazoles under the influence of sodium in liquid ammonia was studied. From the IR and PMR spectra it was established that the compounds obtained have the structures of 7H-pyrrolo[1,2-a0]imidazole and 3H-pyrrolo[1,2-a]benzimidazole derivatives. The debenzylation of 2,3-diphenyl-4-benzylpyrrolo[1,2-a]benzimidazole proceeds with the simultaneous reduction of the pyrrole ring and the formation of 1H-2,3-dihydro-2,3-diphenylpyrrolo[1,2-a]benzimidazole.

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

Literature cited

  1. A. N. Krasovskii, P. M. Kochergin, and A. B. Roman, Khim. Geterotsikl. Soedin., 822 (1971).

  2. P. M. Kochergin, A. A. Druzhinina, and R. M. Palei, Khim. Geterotsikl. Soedin., 149 (1966).

  3. A. A. Druzhinina and P. M. Kochergin, Khim. Geterotsikl. Soedin., 532 (1967).

  4. A. A. Druzhinina, P. M. Kochergin, and N. P. Bychkova, Khim. Geterotsikl. Soedin., 856 (1969).

  5. R. M. Palei and P. M. Kochergin, Khim. Geterotsikl. Soedin., 536 (1967).

  6. R. M. Palei and P. M. Kochergin, Khim. Geterotsikl. Soedin., 865 (1969).

  7. R. M. Palei and P. M. Kochergin, Khim. Geterotsikl. Soedin., 1075 (1969).

  8. R. M. Palei and P. M. Kochergin, Khim. Geterotsikl. Soedin., 572 (1970).

  9. R. G. Jones, J. Am. Chem. Soc., 71, 383 (1949).

    Google Scholar 

  10. J. A. Carbon, J. Org. Chem., 25, 579 (1960).

    Google Scholar 

  11. R. Abraham and H. Bernstein, Can. J. Chem., 37, 1056 (1959); 39, 905 (1961).

    Google Scholar 

  12. F. S. Babichev, G. P. Kutrov, and M. Yu. Kornilov, Ukr. Khim. Zh., 34, 1020 (1968).

    Google Scholar 

  13. N. M. Bortnick and M. F. Fegley, US Patent No. 2,993,046; Chem. Abstr., 56, 4778 (1962).

    Google Scholar 

  14. A. A. Druzhinina and P. M. Kochergin, Khim. Geterotsikl. Soedin., 527 (1967).

  15. W. O. Pool, H. I. Harwood, and A. W. Ralston, J. Am. Chem. Soc., 59, 178 (1937).

    Google Scholar 

  16. A. M. Simonov, N. D. Vitkevich, and B. K. Martsokha, Zh. Obshch. Khim., 30, 3062 (1960).

    Google Scholar 

  17. K. K. Reddy, N. V. Subba Rao, and C. V. Ratha, Indian J. Chem., 1, 96 (1963); Chem. Abstr., 59, 5149 (1963).

    Google Scholar 

  18. S. Takahashi and H. Kano, Chem. Pharm. Bull., 11, No. 11, 1375 (1963).

    Google Scholar 

  19. V. M. Aryuzina and M. N. Shchukina, Khim. Geterotsikl. Soedin., 509 (1968).

Download references

Author information

Authors and Affiliations

Authors

Additional information

See [1] for communication LVII.

Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 6, pp. 826–830, June, 1971.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Kochergin, P.M., Sheinker, Y.N., Druzhinina, A.A. et al. Studies in the imidazole series. Chem Heterocycl Compd 7, 771–775 (1971). https://doi.org/10.1007/BF00476831

Download citation

  • Received:

  • Issue Date:

  • DOI: https://doi.org/10.1007/BF00476831

Keywords

Navigation