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SYNTHESIS OF BI- AND TERTHIOPHENES INITIATED BY MICROWAVE-ASSISTED COUPLING-ISOMERIZATION REACTION

Oliver Grotkopp, Thomas J. J. Müller
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Abstract


The microwave-assisted coupling-isomerization reaction is a practical entry to 1-thienyl-substituted 3-(hetero)arylpropenones, which can be transformed, either stepwise or in a one-pot fashion, via Stetter reaction into thienyl-substituted 1,4-diketones. The terminal Paal–Knorr condensation with Lawesson's reagent gives rise to the formation of bi- or terthiophenes in good yield. The title compounds show substantial blue to blue-green fluorescence upon excitation with UV light.

 


Keywords


thiophenes; alkynylation; cross coupling; cyclocondensation; heterocycles; isomerization; microwave-assisted reactions; one-pot reactions

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