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Letters in Organic Chemistry

Editor-in-Chief

ISSN (Print): 1570-1786
ISSN (Online): 1875-6255

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

Author(s): Krishna C. Majumdar, Pradip K. Maji and Amarta K. Pal

Volume 5 , Issue 3 , 2008

Page: [218 - 223] Pages: 6

DOI: 10.2174/157017808783955772

Price: $65

Abstract

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.

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


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