Regioselective Friedel-Crafts acetylation of 5-hydroxyindole derivatives: synthesis of 4H-pyranoindol-4-one derivatives |
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| Authors: | G. S. Gadaginamath and A. G. Kamat |
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| Affiliation: | (1) Department of Chemistry, Karnatak University, 580003 Dharwad, India |
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| 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. |
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| Keywords: | Friedel-Crafts acetylation of 5-hydroxyindole derivatives Baker-Venkataraman transformation 4H-pyrano(2,3-f)indol-4-one derivatives |
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