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8544222980
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note
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General procedure for the synthesis of (Z) enaminoester 3a-g. A mixture of the appropriate β-ketonic-enol ether (2a-g) (1 equiv), anhydrous zinc chloride (2 equiv) in dry THF was stirred at room temperature for 15 min. The methyl anthranilate (1.2 equiv) was added, and the resulting solution was stirred at room temperature for 24 h, evaporated and diluted with ethyl acetate. The solution was washed with water and sodium bicarbonate aqueous solution (5%), dried and evaporated. The residue was triturated in ether and the resulting solid was recrystallised from isopropyl ether. NMR analysis revealed the formation of (Z) isomers
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22
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8544224438
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note
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General procedure for the synthesis of 4-aroyl-quinolone 1a-g: appropriate enaminoester 3a-g (1 equiv) was added to a solution of sodium (5 equiv) in anhydrous methanol (5 mL) and diphenyl ether (40 mL). The mixture was refluxed for 4 h. After cooling, the pH was adjusted to 4 with 2 N HCl. The solid obtained was collected by filtration and recrystallised
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25
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8544276013
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note
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2 for 4a were observed
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