• Modifications in the iodine oxidation of hydroxy flavanones and their methyl ethers

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      Permanent link:
      https://www.ias.ac.in/article/fulltext/seca/047/03/0184-0190

    • Keywords

       

      Flavone; Naringenin; Dimethyl Ether; Flavanone; Chrysin

    • Abstract

       

      A modified procedure for the action of iodine and silver acetate gives rise to purer products. Agreeing with earlier observations, hesperetin gives a good yield of 3-acetoxy hesperetin and hesperetin 7∶3′-dimethyl ether yields the 3-iodo-compound. The iodoflavanones invariably yield the corresponding flavones by the action of pyridine. In the treatment with alcoholic potash, those which have a free 5-hydroxyl,e.g., 3-iodo naringenin 7∶4′-dimethyl ether and 3-iodo hesperetin 7∶3′-dimethyl ether yield only the corresponding flavones; whereas 3-iodo-5∶7-dimethoxy flavanone having no free 5-hydroxyl group gives a mixture of products, containing the flavone, the flavonol and the 2-hydroxy-2-benzyl 4∶6-dimethoxy coumaranone. The difference seems to depend on the stability of the oxygen ring.

    • Author Affiliations

       

      R N Goel1 V B Mahesh1 T R Seshadri1

      1. Department of Chemistry, Delhi University, Delhi
    • Dates

       
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