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SYNTHESIS OF 3-AMINO-6,7-DIHYDROFERROCENO[a]QUINOLIZIN-4-ONE DERIVATIVES VIA THE REACTION OF 3,4-DIHYDROFERROCENO[c]PYRIDINES WITH AZLACTONES

Владислав Ю. Шувалов, Юлия С. Рожкова, Ирина В. Плеханова, Анастасия С. Костюченко, Юрий В. Шкляев, Александр С. Фисюк
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Abstract


Derivatives of 3-amino-6,7-dihydroferroceno[a]quinolizin-4-one were obtained by the reaction of 3,4-dihydroferroceno[c]pyridines with 4-(ethoxymethylidene)- and 4-(3-oxo-2-benzofuran-1(3H)-ylidene)-2-phenyl-1,3-oxazol-5(4H)-ones (azlactones) in moderate to good yields. The intermediate products of the addition of 4-(ethoxymethylidene)-2-phenyl-1,3-oxazol-5(4H)-one to the alkyl group of 1-alkyl-3,4-dihydroferroceno[c]pyridines were isolated and characterized. The reaction of 4-benzylidene-2-phenyl-1,3-oxazol-5(4H)-one with 3,4-dihydroferroceno[c]pyridines led to the formation of derivatives of 3-amino-2-phenyl-3,4,6,7-tetrahydroferroceno[a]quinolizin-4-one, which were oxidized with DDQ to 3-amino-2-phenyl-6,7-dihydroferroceno[a]quinolizin-4-one.

Keywords


3-amino-4-arylpyridin-2(1H)-one; 3-amino-6,7-dihydroferroceno[a]quinolizin-4-one; azlactone; 3,4-dihydroferroceno[c]pyridine; ferrocene; oxidation; tautomerism.

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