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

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

Volume: 5 Issue: 3

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

Affiliation:

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

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.

Cite this article as:

Majumdar C. Krishna, Maji K. Pradip and Pal K. Amarta, Sequential Thermal and Catalyzed Claisen Rearrangements Toward the Synthesis of Thiocoumarin-Annulated Furopyrans, Letters in Organic Chemistry 2008; 5 (3) . https://dx.doi.org/10.2174/157017808783955772