• Regioselective Friedel-Crafts acetylation of 5-hydroxyindole derivatives: synthesis of 4H-pyranoindol-4-one derivatives

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      https://www.ias.ac.in/article/fulltext/jcsc/106/04/0857-0862

    • Keywords

       

      Friedel-Crafts acetylation of 5-hydroxyindole derivatives; Baker-Venkataraman transformation; 4H-pyrano(2,3-f)indol-4-one derivatives

    • Abstract

       

      The Friedel-Crafts acetylation of 5-hydroxyindole derivativesla-c regioselectively produced 6-acetyl-5-hydroxy-indole derivatives2a-c which were condensed with cinnamic acid using POC13 and dry pyridine to afford 5-cinnamoyloxy-6-acetyl-indoles3a-c. These upon Baker-Venkataraman transformation furnished 6-cinnamoylacetyl-5-hydroxyindoles4a-c which were cyclised separately with AcOH/HCl and Ac2O/AcONa to 4H-pyrano-(2,3-f)indol-4-one derivatives5a-c and6a-c respectively.

    • Author Affiliations

       

      G S Gadaginamath1 A G Kamat1

      1. Department of Chemistry, Karnatak University, Dharwad - 580003, India
    • Dates

       
  • Journal of Chemical Sciences | News

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