Abstract
By the action of alkyl halides the 5-substituted derivatives of 1-benzylbenzimidazole were converted into salts of benzimidazole, debenzylation of which in liquid ammonia with sodium leads to the formation of the less readily available 6-derivatives of 1-alkylbenzimidazoles. This method gives good results during the synthesis of 6-alkyl-, 6-alkoxy-, and 6-aminobenzimidazoles, but because of secondary processes it cannot be used for the production of 6-bromo and 6-nitro derivatives.
This is a preview of subscription content, log in via an institution to check access.
Similar content being viewed by others
References
J. H. Ridde and B. Smith, J. Chem. Soc., 1373, 1960.
L. S. Efros, ZhOKh, 30, 3565, 1960.
A. M. Simonov and P. A. Uglov, ZhOKh, 31, 884, 1951; R. McKee, M. McKee, and R. Bost, J. Am. Chem. Soc. 68, 1904, 1946.
G. Leandri, A. Mangini, and F. Montanari, Gazz. chim. ital., 85, 769, 1955.
H. A. Buch and R. M. Herst, J. Heterocycl. Chem., 3, 198, 1966.
A. F. Pozharskii, é. A. Zvezdina, V. M. Mar'yanovskii, A. M. Simonov, and S. F. Popova, ZhOrKh, 5, 106, 1969.
M. Julia, P. Manoury, and J. Igelen, C. r., 251, 394, 1960. C. A., 55, 7386, 1961.
K. Auwers and W. Mauss, Ber., 61, 2411, 1928.
A. F. Pozharskii, A. M. Simonov, E. A. Zvezdina, and V. A. Anisimova, KhGS [Chemistry of Heterocyclic Compounds], 869, 1969.
Author information
Authors and Affiliations
Additional information
For part III, see [9].
Rights and permissions
About this article
Cite this article
Mar'yanovskii, V.M., Pozharskii, A.F. & Simonov, A.M. Derivatives of imidazole containing potentially labile groupings at the N-atom. Chem Heterocycl Compd 6, 202–204 (1970). https://doi.org/10.1007/BF00474997
Issue Date:
DOI: https://doi.org/10.1007/BF00474997