Abstract
The debenzylation of N-benzylimidazo[1,2-a]benzimidazoles with sodium in liquid ammonia was studied. The debenzylation of the 2-phenyl-substituted derivative is accompanied by hydrogenation of the outer imidazole ring to give 2-phenyl-2,3-dihydro-1H-imidazo[1,2-a]benzimidazole, the alkylation of which in alkaline media and neutral media, respectively, gives the 1-methyl derivative and the 9-methyl derivative. The 1-methyl derivative was subjected to quaternization and bromination; the latter proceeds in the condensed benzene ring. Debenzylation of the 2-methyl derivative of imidazo[1,2-a]benzimidazole is not accompanied by hydrogenation but gives 2-methyl-1(9)H-imidazo[1,2-a]benzimidazole.
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Literature cited
A. M. Simonov, V. A. Anisimova, and T. A. Borisova, Khim. Geterotsikl. Soedin., 111 (1973).
A. M. Simonov, A. A. Belous, V. A. Anisimova, and S. V. Ivanovskaya, Khim.-Farmats. Zh., No. 1, 7 (1969).
R. G. Jones, J. Am. Chem. Soc., 71, 383 (1949).
J. A. Carbon, J. Am. Chem. Soc., 80, 6083 (1958).
P. M. Kochergin, Yu. N. Sheinker, A. A. Druzhinina, R. M. Palei, and L. M. Alekseeva, Khim. Geterotsikl. Soedin., 826 (1971).
J. A. Carbon, J. Org. Chem., 25, 579 (1960).
V. S. Ponomar' and P. M. Kochergin, Khim. Geterotsikl. Soedin., 253 (1972).
R. M. Palei, “Synthesis and some transformations of pyrrolo[1,2-a]benzimidazole derivatives,” Author's Abstract of Dissertation, Moscow (1969), p. 23.
R. J. North and A. R. Day, J. Heterocycl. Chem., 6, 655 (1969).
L. N. Yakhontov and M. S. Sokolov, Khim. Geterotsikl. Soedin., 1111 (1969).
P. Baumgartner, R. Paioni, and W. Jenny, Helv. Chim. Acta, 54, 266 (1971).
A. M. Simonov and V. A. Anisimova, Khim. Geterotsikl. Soedin., 1102 (1968).
Reactions and Methods for the Investigation of Organic Compounds [Russian translation], Vol. 20, Khimiya, Moscow (1969).
H. O. House, Modern Synthetic Reactions, W. A. Benjamin, Inc. (1965), p. 50.
A. M. Simonov, V. A. Anismova, and L. E. Grushina, Khim. Geterotsikl. Soedin., 838 (1970).
L. C. King, J. Am. Chem. Soc., 66, 894 (1944).
N. O. Saldabol, L. L. Zeligman, and S. A. Giller, Khim. Geterotsikl. Soedin., 860 (1971).
N. Fuson, M. L. Josien, R. L. Powell, and E. Utterbark, J. Chem. Phys., 20, 145 (1952).
E. Lieber, D. R. Levering, and L. J. Patterson, Anal. Chem., 23, 1594 (1951).
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See [1] for communication VI.
Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 6, pp. 791–796, June, 1973.
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Anisimova, V.A., Simonov, A.M. & Borisova, T.A. Research on imidazo [1,2-a]benzimidazole derivatives. Chem Heterocycl Compd 9, 726–730 (1973). https://doi.org/10.1007/BF00472317
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DOI: https://doi.org/10.1007/BF00472317