Advertisement

Synthetic experiments in the benzopyrone series

Part XII. A synthesis of 7-O-methyl-ethers of hydroxy flavones
  • N. Narasimhachari
  • T. R. Seshadri
Article
  • 20 Downloads

Summary

A general method for the synthesis of the 7-methyl ethers of hydroxy flavones is described using as examples (1) tectochrysin, (2) genkwanin and (3) 7-O-methyl luteolin. It consists in preparing the corresponding 7-O-methyl flavanone and oxidising it with iodine. 7-O-Methyl eriodictyol is now made from (a) 2∶3′-dihydroxy-4∶6∶4′-trimethoxy chalkone and (b) 2-hydroxy-4∶6-dimethoxy-3′∶4′-dibenzoyloxy chalkone by treatment with hydrobromic acid. Iodine oxidation of it yields (3). The constitution of this product is confirmed by fully ethylating it and showing that the triethyl ether is identical with 7-methoxy-5∶3′∶4′-triethoxy flavone.

Keywords

Flavone Luteolin Chrysin Hydrobromic Acid Anhydrous Potassium Carbonate 
These keywords were added by machine and not by the authors. This process is experimental and the keywords may be updated as the learning algorithm improves.

References

  1. 1.
    Kuhn and LowChem. Abs., 1945, 3285.Google Scholar
  2. 2.
    PiccardBer., 1873,6, 884. Rao, Rao and SeshadriProc. Ind. Acad. Sci., A, 1947,25, 430.Google Scholar
  3. 3.
    Gulati and VenkataramanJ.C.S., 1936, 267. Rao and SeshadriProc. Ind. Acad. Sci., A, 1945,22, 383 andJ.C.S., 1947, 122.Google Scholar
  4. 4.
    Rao, Rao and SeshadriProc. Ind. Acad. Sci. A, 1947,25, 431.Google Scholar
  5. 5.
    Narasimhachari and SeshadriIbid.,, 1949,29, 265.Google Scholar
  6. 6.
    Ibid.,, 1949,30, 151.Google Scholar
  7. 7.
    Mahal and VenkataramanJ.C.S., 1936, 569.Google Scholar
  8. 8.
    Narasimhachari and SeshadriProc. Ind. Acad. Sci., A, 1949,30, 271.Google Scholar
  9. 9.
    Diller and KostaneckiBer., 1901, 1449.Google Scholar
  10. 10.
    Russel and ToddJ.C.S., 1934, 218.Google Scholar
  11. 11.
    Fergusonet al. Nature, 1949,163, 606.Google Scholar
  12. 12.
    Ferguson Private communication.Google Scholar

Copyright information

© Indian Academy of Sciences 1950

Authors and Affiliations

  • N. Narasimhachari
    • 1
  • T. R. Seshadri
    • 1
  1. 1.Department of ChemistryDelhi UniversityDelhi

Personalised recommendations