Abstract
In contrast to 1-amino- and 1-alkylaminobenzimidazoles, 1-di-alkylaminobenzimidazoles are metallated by n-butyl-lithium in absolute either at the 2-position. The subsequent treatment of the lithium derivatives by electrophilic reagents, in which role benzophenone and iodine were used, leads to the formation of the corresponding 2-R-1-dialkylaminobenzimidazoles, which are difficult to obtain by other methods. The possibility was studied of using the N-dialkylamino group as a protective function.
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V. V. Kuz'menko and A. F. Pozharskii, Adv. Heter. Chem., 53, 85 (1992).
T. A. Kuz'menko, V. V. Kuz'menko, A. F. Pozharskii, and V. A. Anisimova, Khim. Geterotsikl. Soedin, No. 11, 1517 (1990).
A. F. Pozharskii, V. V. Kuz'menko, A. A. Bumber, E. S. Petrov, M. I. Terekhova, N. L. Chikina, and I. M. Nanavyan, Khim. Geterotsikl. Soedin, No. 2, 221 (1989).
D. W. S. Latham, O. Meth-Cohn, and H. Suschitzky, Chem. Commun., No. 2, 41 (1973).
A. F. Pozharskii, E. A. Zvezdina, I. S. Kashparov, Yu. P. Andreichikov, V. M. Maryanovskii, and A. M. Simonov, Khim. Geterotsikl. Soedin., No. 9, 1230 (1971).
A. F. Pozharskii, E. A. Zvezdina, V. I. Sokolov, and I. S. Kashparov, Chem. Ind. (London), 256 (1972).
A. F. Wagner, P. E. Wittreich, A. Lusi, and K. Folkes, J. Org. Chem., 27, 3236 (1962).
T. L. Gilchrist, C. J. Harris, F. D. King, M. E. Peak, and C. W. Rees, J. Chem. Soc, Perkin I., No. 8, 2169 (1988).
M. N. Sheng and A. R. Day, J. Org. Chem., 28, 736 (1963).
B. A. Porai-Koshits, O. F. Ginzburg, and L. S. Efros, Zh. Obshch. Khim., 17, 1768 (1947).
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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 9, pp. 1196–1201, September, 1992.
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Kuz'menko, V.V., Filatova, I.A. & Pozharskii, A.F. Metallation of 1-dialkylaminobenzimidazoles. Chem Heterocycl Compd 28, 1009–1014 (1992). https://doi.org/10.1007/BF00531477
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DOI: https://doi.org/10.1007/BF00531477