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Synthesis and some transformations of 2-(2-thienyl)-1(3)H-imidazo[4,5-f] quinoline

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Abstract

2-(2-Thienyl)-1(3)H-imidazo{cm[4,5-f]}quinoline was synthesized by the Weidenhagen reaction of quinoline-5,6-diamine with thiophene-2-carbaldehyde. Its methylation in the system KOH-DMSO gave isomeric 1-methyl-2-(2-thienyl)-1H- and 3-methyl-2-(2-thienyl)-3H-imidazo{cm[4,5-f]}quinolines, the latter being the major product. The 3-methyl derivative was subjected to electrophilic substitution reactions (bromination, nitration, formylation, acylation, sulfonation). Depending on the conditions, electrophilic attack was directed at the thiophene or quinoline fragment or both these.

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Authors and Affiliations

  1. South Russian State Technical University (Novocherkassk Polytechnic Institute), ul. Prosveshcheniya 132, Novocherkassk, 346428, Russia

    A. A. Aleksandrov, M. M. El’chaninov & A. S. Dedeneva

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  1. A. A. Aleksandrov
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  2. M. M. El’chaninov
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  3. A. S. Dedeneva
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Correspondence to A. A. Aleksandrov.

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Original Russian Text © A.A. Aleksandrov, M.M. El’chaninov, A.S. Dedeneva, 2012, published in Zhurnal Obshchei Khimii, 2012, Vol. 82, No. 7, pp. 1163–1167.

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Aleksandrov, A.A., El’chaninov, M.M. & Dedeneva, A.S. Synthesis and some transformations of 2-(2-thienyl)-1(3)H-imidazo[4,5-f] quinoline. Russ J Gen Chem 82, 1263–1266 (2012). https://doi.org/10.1134/S1070363212070134

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  • DOI: https://doi.org/10.1134/S1070363212070134

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