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Sequential Thermal and Catalyzed Claisen Rearrangements Toward the Synthesis of Thiocoumarin-Annulated Furopyrans

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Regioselective synthesis of a hitherto unreported thiocoumarin-annulated furopyran moiety was achieved by the application of Claisen rearrangement in which a second Claisen rearrangement was achieved by anhydrous aluminum chloride. The precursor endocyclic compounds for catalyzed Claisen rearrangement were synthesized by the thermal [3,3] sigmatropic rearrangement of the corresponding ether.

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Keywords: 1-aryloxy-4-chlorobut-2-yne; 4-hydroxythiocoumarin; Anhydrous aluminum chloride; furopyrans; intramolecular hydroaryloxylation; sequential Claisen rearrangement

Document Type: Research Article

Publication date: 2008-04-01

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  • Letters in Organic Chemistry publishes original letters on all areas of organic chemistry including synthesis, bioorganic, medicinal, natural products, organometallic, supramolecular, molecular recognition and physical organic chemistry. The emphasis is placed on publishing quality papers very rapidly. Letters are processed rapidly and take full advantage of the Internet technology both for the submission and the review of the manuscripts.
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