Synthesis of 5-aryl-2-hydroxy-2-(trifluoromethyl)furan-3(2H)-ones and their reactions with aromatic 1,2-diamines, hydrazine and hydroxylamine

Add time:08/24/2019    Source:sciencedirect.com

2-(Trifluoromethyl)furanones were obtained in good yields via the Claisen condensation of acetophenones with methyl 2-methoxytetrafluoropropionate, followed by sulfuric acid-mediated deprotection of the reaction products. These compounds react with 2,3-diaminopyridine, o-phenylenediamine and 2,3-diaminonaphthalene in refluxing acetic acid to give the corresponding quinoxaline derivatives, the regioisomeric and tautomeric composition of which was investigated. Reactions of 2-(trifluoromethyl)furanones with hydrazines and hydroxylamine proceeded regioselectively and gave pyridazine, pyrazole and isoxazole derivatives in high yields. Their regiochemistry was established by X-ray diffraction analysis.

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