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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• 作者：Sergey A. Usachev ; Boris I. Usachev ; Vyacheslav Ya. Sosnovskikh
• 关键词：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
• 刊名：Tetrahedron
• 出版年：7 January, 2014
• 年：2014
• 卷：70
• 期：1
• 页码：60-66
• 全文大小：429 K

文摘

Treatment of ethyl 4-aryl-6-(trifluoromethyl)-2-oxo-2H-pyran-3-carboxylates, prepared from 4,4,4-trifluorobutane-1,3-diones, PCl₅聽and sodium diethyl malonate, with sulfuric acid afforded the intramolecular Friedel-Crafts acylation products, 3-(trifluoromethyl)indeno[2,1-c]pyran-1,9-diones, from which 2-(trifluoromethyl)-6H-pyrano[3,4-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.