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Nuclear oxidation in flavones and related compounds

Part XXXII. Some coumarin derivatives

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Summary

It is suggested that umbelliferone is a fundamental compound in the biogenesis of coumarins and that other important hydroxycoumarins involve further stages of oxidation. In support of this idea experiments are described for the preparation from umbelliferone of æsculetin byp-oxidation and daphnetin byortho-oxidation. From either of these dihydroxycoumarins, 6:7:8-trihydroxycoumarin can be prepared. Limettin would, however, appear to have a different origin. The possible evolution of fraxinol from limettin byp-oxidation is supported by persulphate oxidation experiments using 4-methyl limettin. 4-Methyl fraxinol has also been synthesised from 2:6-dimethoxyquinol and acetoacetic ester.

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Authors and Affiliations

  1. Department of Chemistry, Delhi University, Delhi

    P. L. Sawhney, T. R. Seshadri F.A.Sc. & T. R. Thiruvengadam

Authors
  1. P. L. Sawhney
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  2. T. R. Seshadri F.A.Sc.
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  3. T. R. Thiruvengadam
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Sawhney, P.L., Seshadri, T.R. & Thiruvengadam, T.R. Nuclear oxidation in flavones and related compounds. Proc. Indian Acad. Sci. (Math. Sci.) 33, 11–21 (1951). https://doi.org/10.1007/BF03172254

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  • DOI: https://doi.org/10.1007/BF03172254

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