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Synthetical experiments in the chromone group

Part XXVII. Coupling of 5-hydroxyflavone, 5-hydroxy-6-methoxyflavone and tectochrysin with diazotized aniline. New synthesis of 5∶6-dihydroxyflavone, baicalein, and 5∶6∶8-trihydroxyflavone

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Summary

The coupling of 5-hydroxyflavone with benzenediazonium chloride led to an azo dye which was different from the compound obtained by the Robinson flavone condensation on 2-acetyl-4-benzeneazoresorcinol and benzoic anhydride. The two compounds are shown to be the 8- and 6-benzeneazo derivatives of 5-hydroxyflavone respectively. The conversion of both the azo dyes into 5∶6-dihydroxyflavone is described.

Tectochrysin was converted to baicalein 7-methyl ether by coupling with benzenediazonium chloride, followed by reduction of the azo dye to the amine and treatment of the latter with hydrochloric acid. Baicalein was obtained by demethylation of the 7-methyl ether. The same series of reactions carried out on 5-hydroxy-6-methoxyflavone25 led to 5∶6∶8-trihydroxyflavone.

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Authors and Affiliations

  1. Department of Chemical Technology, University of Bombay, Bombay

    R. N. Iyer & K. Venkataraman F.A.Sc.

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  1. R. N. Iyer
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  2. K. Venkataraman F.A.Sc.
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Iyer, R.N., Venkataraman, K. Synthetical experiments in the chromone group. Proc. Indian Acad. Sci. 37, 629–642 (1953). https://doi.org/10.1007/BF03052691

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  • DOI: https://doi.org/10.1007/BF03052691

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