Abstract
2-Ethoxycarbonyl-5,6,7,8-tetrafluorochromone reacts with methylamine differently, depending on the solvent nature and the amount of the amine: in DMSO and MeCN, the fluorine atom at the C(7) atom is initially replaced and then the C(2) and/or C(9) are attacked, while in ethanol, the reaction involves the C(2) atom with opening of the pyrone ring. The reaction of 3-ethoxycarbonyl-5,6,7,8-tetrafluoro-2-methylchromone with methylamine results, regardless of the solvent, in opening of the chromone ring and the formation of intermediate ethyl 3-(3,4,5,6-tetrafluoro-2-hydroxyphenyl)-2-(1-methylamino)ethylidene-3-oxopropionate, which undergoes intramolecular cyclization to give 5,6,7,8-tetrafluoro-3-(1-methyl-amino)ethylidene-3,4-dihydro-2H-benzopyran-2,4-dione.
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Dedicated to Academician N. S. Zefirov on the occasion of his 70th birthday.
Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 9, pp. 2093–2098, September, 2005.
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Shcherbakov, K.V., Burgart, Y.V. & Saloutin, V.I. Reactions of 2(3)-ethoxycarbonyl-5,6,7,8-tetrafluorochromones with methylamine. Russ Chem Bull 54, 2157–2162 (2005). https://doi.org/10.1007/s11172-006-0091-8
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DOI: https://doi.org/10.1007/s11172-006-0091-8