Both visnaginone and khellinone react with malononitrile, ethyl cyanoacetate or cyanoacetamide in presence of ammonium acetate to give substituted furobenzopyrans or furobenzopyridones.However, the reaction of visnaginone and khellinone with aldehydes, and malononitrile in presence of ammonium acetate leads to the formation of the corresponding 2-amino-4,6-disubstituted pyridine 3-carbonitriles. The latter compounds are also obtained by treating the respective chalcones with malononitrile and ammonium acetate.3-Substituted 1,3-diketobutyrates form with malononitrile or with cyanoacetamide and ammonium acetate the 2-amino-4,6-disubstituted pyridine-3-carbonitriles or the 4,6-di-substituted cyanopyridones, respectively
Die durch Umsetzen der Triketomonohydrazone (I) mit Phenyl‐ bzw. Benzylmagnesiumhalogenid über die entsprechenden ungesättigten Alkohole (II) addieren Hydrazin unter Bildung von Pyrazolidinen (die Verbindungen (III) wurden dargestellt.
Durch Claisen‐Kondensation werden aus den Benzofuranen (I) die Diketoderivate (II) synthetisiert, die mit aromatischen Diazoverbindungen zu (IV) gekuppelt werden.
Durch Reaktion der Benzofurane (Ia) (= Visnaginon) und (Ib) (= Khellinon) mit den Verbindungen (II), (III) bzw. (V) sowie mit (II) und den Aldehyden (VII) entstehen die Furobenzopyrane (IV) bzw. die Furochinoline (VI) sowie die Pyridine (VIII).
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