• Nuclear oxidation in flavones and related compounds - Part XV. Further synthesis of 7∶8-hydroxy-flavonols application of dakins reaction for ortho-oxidation

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      https://www.ias.ac.in/article/fulltext/seca/028/03/0098-0102

    • Keywords

       

      Flavone; Fisetin; Persulphate; Hexamine; Anhydrous Potassium Carbonate

    • Abstract

       

      In continuation of Part VIII, members of the 3-methoxy-7-hydroxyflavone series with one, two and three methoxyl groups in the side phenyl nucleus are subjected to ortho-oxidation with alkaline persulphate; the yield of the corresponding 7∶8-hydroxy compounds is 10 to 15%. On the other hand, attempts at ortho-oxidation by this method in the side phenyl nucleus have failed just as in several cases of simpler benzene derivatives. It is suggested that ortho-oxidation in nature should be considered to take place in multiple stages and this has been verified using a convenient example in the flavone series. 3-Methoxy-7-hydroxy-flavone undergoes change into the corresponding 8-aldehyde by the action of hexamine and this is converted into 3-methoxy-7∶8-dihydroxy flavone by means of alkaline hydrogen peroxide, the yields being very good.

    • Author Affiliations

       

      L Ramachandra Row1 T R Seshadri1 T R Thiruvengadam1

      1. Department of Chemistry, Andhra University, Waltair
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