Abstract
2-(2-Furyl)-1(3)H-imidazo[4,5-f]quinoline was synthesized by the Weidenhagen reaction of quinoline-5,6-diamine with furfural. Its alkylation with methyl iodide in the system KOH-DMSO gave two isomeric N-methyl derivatives, 2-(2-furyl)-1-methyl-1H- and 2-(2-furyl)-3-methyl-3H-imidazo[4,5-f]quinolines, the latter prevailing. 2-(2-Furyl)-3-methyl-3H-imidazo[4,5-f]quinoline was brought into electrophilic substitution reactions: bromination, nitration, formylation, acylation, sulfonation. Depending on the reaction conditions, electrophilic attack could be directed at both furan ring and quinoline fragment.
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References
Oleinikova, L.Ya., Cand Sci. (Chem.) Dissertation, Rostov-on-Don, 1972.
Weidenhagen, R., Ber., 1936, p. 2263.
El’chaninov, M.M., Oleinikova, L.Ya., and Simonov, A.M., Khim. Geterotsikl. Soedin., 1979, p. 1047.
Pechkin, A.A. and El’chaninov, M.M., Izv. Vyssh. Uchebn. Zaved. Sev.-Kav. Regiona, Estestv. Nauki, 2000, p. 48.
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Original Russian Text © A.A. Aleksandrov, A.S. Dedeneva, E.V. Vlasova, M.M. El’chaninov, 2011, published in Zhurnal Organicheskoi Khimii, 2011, Vol. 47, No. 1, pp. 121–124.
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Aleksandrov, A.A., Dedeneva, A.S., Vlasova, E.V. et al. 2-(2-Furyl)-1(3)H-imidazo[4,5-f]quinoline. Synthesis and electrophilic substitution reactions. Russ J Org Chem 47, 120–123 (2011). https://doi.org/10.1134/S1070428011010155
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DOI: https://doi.org/10.1134/S1070428011010155