Abstract
1-Methyl-2-(thiophen-3-yl)-1H-benzimidazole was synthesized by the Weidenhagen reaction, followed by N-methylation. Electrophilic substitution reactions of the title compound, in particular nitration, bromination, sulfonation, formylation, and acylation, were studied. The formylation and acylation in polyphosphoric acid afforded mixtures of 2- and 5-substituted isomers at the thiophene ring. The nitration of 1-methyl-2-(thiophen-3-yl)-1H-benzimidazole involved the thiophene ring or both thiophene and benzene fragments, depending on the conditions. Steric arrangement of the heterocycles in the 1-methyl-2-(thiophen-3-yl)-1H-benzimidazole molecule was analyzed by quantum chemical calculations.
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References
El’chaninov, M.M., Doctoral (Chem.) Dissertation, Rostov-on-Don, 2006.
Weidenhagen, R., Ber., 1936, vol. 69, p. 2263.
Achkasova A.A., Elchaninov, M.M., Milov, A.A., and Lukyanov, B.S., Chem. Heterocycl. Compd., 2005, vol. 41, p. 1494.
Elchaninov, M.M., Simonov, A.M., and Oleinikova, L.Ya., Chem. Heterocycl. Compd., 1983, vol. 19, p. 1041.
Paquette, L.A., Principles of Modern Heterocyclic Chemistry, New York W.A. Benjamin, 1968.
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Original Russian Text © M.M. El’chaninov, A.A. Aleksandrov, 2016, published in Zhurnal Organicheskoi Khimii, 2016, Vol. 52, No. 1, pp. 54–57.
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El’chaninov, M.M., Aleksandrov, A.A. Synthesis and some transformations of 1-methyl-2-(thiophen-3-yl)-1H-benzimidazole. Russ J Org Chem 52, 47–50 (2016). https://doi.org/10.1134/S1070428016010097
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DOI: https://doi.org/10.1134/S1070428016010097