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Regioselective Synthesis of Thieno[3,2-c][1]benzopyran-4-ones by Thio-Claisen Rearrangement

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Summary.

A number of thieno[3,2-c][1]benzopyran-4-ones, potential antiinflamatory, antipyretic, and antiallergic drugs, are synthesized in 65–80% yield by thermal thio-Claisen rearrangement of 4-allylthio[1]benzopyran-2-ones in refluxing quinoline for 0.5–8.0 h. The 4-allylthio[1]benzopyran-2-ones are in turn prepared in 75–85% yield from 4-mercaptocoumarin and different allylic halides by phase-transfer-catalysed alkylation with TBAB or BTEAC catalyst in chloroform-aq. NaOH at room temperature.

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Authors and Affiliations

  1. Department of Chemistry, University of Kalyani, 741 235, Kalyani, West Bengal, India

    Krishna C. Majumdar & Anindita Biswas

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  1. Krishna C. Majumdar
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  2. Anindita Biswas
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Correspondence to Krishna C. Majumdar.

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Majumdar, K., Biswas, A. Regioselective Synthesis of Thieno[3,2-c][1]benzopyran-4-ones by Thio-Claisen Rearrangement. Monatshefte für Chemie 135, 1001–1007 (2004). https://doi.org/10.1007/s00706-003-0164-4

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  • DOI: https://doi.org/10.1007/s00706-003-0164-4

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