Heterocyclic analogs of thioflavones: synthesis and NMR spectroscopic investigations

The synthesis of several hitherto unknown heterocyclic ring systems derived from thioflavone is described. Coupling of various o-haloheteroarenecarbonyl chlorides with phenylacetylene gives 1-(o-haloheteroaryl)-3-phenylprop-2-yn-1-ones, which were treated with NaSH in refluxing ethanol to yield the...

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Veröffentlicht in:	Molecules (Basel, Switzerland) Switzerland), 2009-09, Vol.14 (9), p.3814-3832
Hauptverfasser:	Fuchs, Ferdinand C, Eller, Gernot A, Holzer, Wolfgang
Format:	Artikel
Sprache:	eng
Schlagworte:	Flavones - chemical synthesis Flavones - chemistry Heterocyclic Compounds - chemical synthesis Heterocyclic Compounds - chemistry Magnetic Resonance Spectroscopy NMR spectroscopy ring closure reactions Sonogashira coupling thioflavone
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Beschreibung
Zusammenfassung:	The synthesis of several hitherto unknown heterocyclic ring systems derived from thioflavone is described. Coupling of various o-haloheteroarenecarbonyl chlorides with phenylacetylene gives 1-(o-haloheteroaryl)-3-phenylprop-2-yn-1-ones, which were treated with NaSH in refluxing ethanol to yield the corresponding bi- and tricyclic annelated 2-phenylthiopyran-4-ones. Detailed NMR spectroscopic investigations of the ring systems and their precursors are presented.
ISSN:	1420-3049 1420-3049
DOI:	10.3390/molecules14093814