Synthesis of 3-(trifluoromethyl)indeno[2,1-c]pyran-1,9-diones from 4-aryl-3-carbethoxy-6-(trifluoromethyl)-2-pyrones and their reaction with sodium azide leading to new carbostyril derivatives |
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Authors: | Sergey A Usachev Boris I UsachevVyacheslav Ya Sosnovskikh |
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Institution: | Department of Chemistry, Ural Federal University, Pr. Lenina 51, 620000 Ekaterinburg, Russian Federation |
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Abstract: | Treatment of ethyl 4-aryl-6-(trifluoromethyl)-2-oxo-2H-pyran-3-carboxylates, prepared from 4,4,4-trifluorobutane-1,3-diones, PCl5 and sodium diethyl malonate, with sulfuric acid afforded the intramolecular Friedel–Crafts acylation products, 3-(trifluoromethyl)indeno2,1-c]pyran-1,9-diones, from which 2-(trifluoromethyl)-6H-pyrano3,4-c]quinoline-4,5-diones were obtained via the Schmidt reaction in moderate yields. The latter reacted with sodium azide to give 2-oxo-4-(5-trifluoromethyl-1,2,3-triazol-4-yl)-1,2-dihydroquinoline-3-carboxylic acids in good yields. |
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Keywords: | 2-Pyrones Friedel&ndash Crafts acylation Indeno[2 1-c]pyran-1 9-diones Schmidt reaction Pyrano[3 4-c]quinoline-4 5-diones Triazoles Trifluoromethylated heterocycles |
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