Synthesis and properties of 2-(furan-2-yl)thiazolo[5,4-<Emphasis Type="Italic">f</Emphasis>]quinoline |
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Authors: | M M El’chaninov А А Aleksandrov |
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Institution: | 1.Platov South-Russian State Polytechnic University,Novocherkassk,Russia |
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Abstract: | N-(Quinolin-6-yl)furan-2-carboxamide was prepared by the coupling of quinoline-6-amine with furan-2-carbonyl chloride in propan-2-ol. Treatment of the product with excess Р2S5 in anhydrous pyridine gave N-(quinolin-6-yl)furan-2-carbothioamide which was oxidized with potassium ferricyanide in an alkaline medium by the Jakobson procedure to obtain 2-(furan-2-yl)thiazolo5,4-f]quinoline. The latter was subjected to electrophilic substitution reactions (nitration, bromination, formylation, and acylation), as well as characteristic nucleophilic substitution involving the quinoline ring and quaternization with methyl iodide in benzene. |
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