Interaction of methyl-3-[(dimethylamino)methylidene]-4-oxo-6-fluoro-3,4-dihydro-2H-chromane-2-carboxylate with aromatic amines
DOI:
https://doi.org/10.15407/dopovidi2015.08.106Keywords:
3;4-dihydro-2H-chroman-4-on, N;N-dimethylformamide dimethylacetal, secondary amine, Z/E-isomerismAbstract
A convenient efficient method for the synthesis of methyl-3-[(dimethylamino)methylidene]-4-oxo-6-fluoro-3,4-dihydro-2H-chromane-2-carboxylate has been proposed. The interaction of methyl-3-[(dimethylamino)methylidene]-4-oxo-6-fluoro-3,4-dihydro-2H-chromane-2-carboxylate with aromatic amines has been studied. It has been demonstrated that the obtained 3-(aminomethylen)-6-fluorochroman-4-oxo-2-carboxylates exist in a solution as a mixture of Z/E-isomers with respect to the exocyclic double C=C bond. With the help of NMR methods, it is proved that the determining factor in the isomeric composition is solvation effects, and the balance can easily shifted t toward one of the isomers.
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