カルコン, フラバノン型化合物の合成研究(第1報) : 含窒素カルコシ型化合物の合成その1

概要

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Condensation of resacetophenone (III) and 2 -, 3-, or 4-pyridinecarboxaldehydes (IV, V, VI) in the presence of alkali afforded, though in a low yield, the corresponding 2', 4'-dihydroxy-2-, 3-, or 4-azachalcones (VII, VIII, IX). The use of 4'-(benzyloxy)-2'-hydroxyacetophenone (X) instead of III in the reaction with IV to VI afforded the corresponding 4'-(benzyloxy)-2'-hydroxy-2-, 3-, or 4-azachalcones (XI, XII, XIII) in a comparatively good yield. Heating of XI to XIII with conc. hydrochloric acid in glacial acetic acid resulted in facile debenzylation and the corresponding dihydroxy derivatives (VII, VIII, IX) were obtained. The 4'-hydroxyl group in these dihydroxy derivatives was assumed to be forming a salt with the nitrogen atom in the pyridine ring from the examination of their infrared spectra.
1968-08-25