• Synthetic experiments in the benzopyrone series - Part IX. Partial demethylation of chalkones: A synthesis of sakuranetin

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      https://www.ias.ac.in/article/fulltext/seca/029/04/0265-0268

    • Keywords

       

      Naringenin; Flavanone; Monomethyl Ether; Hydrobromic Acid; Dimethyl Sulphate

    • Abstract

       

      Partial demethylation of 2-hydroxy-4 ∶ 6-dimethoxy chalkone with aluminium chloride yields 2 ∶ 4-dihydroxy-6-methoxychalkone which could be cyclised to 5-methoxy-7-hydroxy-flavanone. The use of hydrobromic acid for the demethylation produces directly 5-hydroxy-7-methoxy flavanone due to initial ring closure and subsequent demethylation in the 5-position of the flavanone. When this reagent acts on 2-hydroxy-4 ∶ 6 ∶ 4′-trimethoxy chalkone sakuranetin, the naturally occurring monomethyl ether of naringenin is produced.

    • Author Affiliations

       

      N Narasimhachari1 T R Seshadri1

      1. Department of Chemistry, Andhra University, Waltair
    • Dates

       
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