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Synthetic experiments in the benzopyrone series

Part XLII. A new synthesis of 5 : 6 : 7-trihydroxy isoflavone derivatives

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Summary

Using the more easily accessible 5:7: 8-trihydroxy derivatives of isoflavones a convenient method has been worked out for the synthesis of 5: 6: 7-trihydroxy derivatives. It consists in the alkali fission of 5-hydroxy-7: 8-dimethoxy isoflavone and its 2-methyl derivative to yield 2: 6-dihydroxy-3: 4-dimethoxy-phenyl-benzyl ketone. This ketone on treatment with ethyl formate and sodium yields 5-hydroxy-6 : 7-dimethoxy isoflavone. Vigorous acetylation of the ketone using acetic anhydride and sodium acetate yields 2-methyl-5-hydroxy-6: 7-dimethoxy isoflavone which is compared with an authentic sample prepared by an independent method. 5-Hydroxy-7 : 8-dimethoxy isoflavone yields a small quantity of 5-hydroxy 6: 7-dimethoxy isoflavone during alkali fission.

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Authors and Affiliations

  1. Department of Chemistry, Delhi University, India

    V. B. Mahesh, N. Narasimhachari & T. R. Seshadri

Authors
  1. V. B. Mahesh
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  2. N. Narasimhachari
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  3. T. R. Seshadri
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Mahesh, V.B., Narasimhachari, N. & Seshadri, T.R. Synthetic experiments in the benzopyrone series. Proc. Indian Acad. Sci. 39, 165–175 (1954). https://doi.org/10.1007/BF03048535

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  • DOI: https://doi.org/10.1007/BF03048535

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