2-(2-Furyl)-1(3)H-imidazo[4,5-f]quinoline. Synthesis and electrophilic substitution reactions |
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Authors: | A A Aleksandrov A S Dedeneva E V Vlasova M M El’chaninov |
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Institution: | 1. South Russian State Technical University (Novocherkassk Polytechnical Institute), ul. Prosveshcheniya 132, Novocherkassk, 346428, Russia
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Abstract: | 2-(2-Furyl)-1(3)H-imidazo4,5-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-imidazo4,5-f]quinolines, the latter prevailing. 2-(2-Furyl)-3-methyl-3H-imidazo4,5-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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