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Molecules 2009, 14(9), 3814-3832; doi:10.3390/molecules14093814
Article

Heterocyclic Analogs of Thioflavones: Synthesis and NMR Spectroscopic Investigations

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Received: 3 September 2009 / Revised: 11 September 2009 / Accepted: 21 September 2009 / Published: 25 September 2009
(This article belongs to the Special Issue Advances in Heterocyclic Chemistry)
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Abstract

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.
Keywords: thioflavone; Sonogashira coupling; ring closure reactions; NMR spectroscopy thioflavone; Sonogashira coupling; ring closure reactions; NMR spectroscopy
This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

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Fuchs, F.C.; Eller, G.A.; Holzer, W. Heterocyclic Analogs of Thioflavones: Synthesis and NMR Spectroscopic Investigations. Molecules 2009, 14, 3814-3832.

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