Skip to main content
SpringerLink
Log in

Selective demethylation of the 5-methoxyl group in flavanones and synthesis of dihydrowogonin

  • Published:
Proceedings of the Indian Academy of Sciences - Section A Aims and scope Submit manuscript

Summary

Anhydrous aluminium chloride in ether solution is found to be a convenient reagent for the selective demethylation of the 5-position of methoxy flavanones and these 5-hydroxy compounds can serve as standard derivatives for comparison. A number of typical compounds are reported, the most important being naringenin dimethyl ether, citronetin monomethyl ether and carthamidin and isocarthamidin trimethyl ethers. The method has been employed for the synthesis of dihydrowogonin which has been recently isolated. This involves the preparation and partial demethylation of 7-hydroxy-5:8-dimethoxy flavanone.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Similar content being viewed by others

References

  1. Schönberg and BadranJ.A.C.S., 1951,73, 2960;

    Article  Google Scholar 

  2. Mukerjee and SeshadriProc. Ind. Acad. Sci., 1952,35 A, 326.

    Google Scholar 

  3. Dharet al. Journ. Sci. Ind. Res., 1955,14 B, 73;

    Google Scholar 

  4. Maheshet al. Proc. Ind. Acad. Sci., 1954,39 A, 166.

    Google Scholar 

  5. Baker and SimmondsJ.C.S-, 1940, 1373.

  6. Narasimhachari and SeshadriProc. Ind. Acad. Sci., 1948,27 A, 236.

    Google Scholar 

  7. —, 1949,29 A, 265;

    Google Scholar 

  8. —, 1950,32 A, 21.

    Google Scholar 

  9. Rao and Seshadri —, 1946,23 A, 213.

    Google Scholar 

  10. Shinoda and SatoJ. Pharm. Soc., Japan, 1928,48, 933;

    Google Scholar 

  11. Narasimhachari and SeshadriProc. Ind. Acad. Sci., 1948,27 A, 234.

    Google Scholar 

  12. Shinoda and SatoChem. Abs., 1932,26, 1916;

    Google Scholar 

  13. Narasimhachariet al. Proc. Ind. Acad. Sci., 1953,37 A, 626.

    Google Scholar 

  14. Mentzetet al. Bull. Soc. Chim. Biol., 1954,36, 1137;

  15. Chopinet al. Compt. Rend., 1956,243, 712.

    Google Scholar 

  16. Wesseley and MoserMonatsh., 1930,56, 97.

    Article  Google Scholar 

  17. Chopin and DelepineCompt. Rend., 1956,243, 745.

    Google Scholar 

  18. Molhoet al. —, 1957,244, 470.

    Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Department of Chemistry, University of Delhi, Delhi

    S. N. Aiyar, Ishwar Dass & T. R. Seshadri

Authors
  1. S. N. Aiyar
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Ishwar Dass
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. T. R. Seshadri
    View author publications

    You can also search for this author in PubMed Google Scholar

Rights and permissions

Reprints and permissions

About this article

Cite this article

Aiyar, S.N., Dass, I. & Seshadri, T.R. Selective demethylation of the 5-methoxyl group in flavanones and synthesis of dihydrowogonin. Proc. Indian Acad. Sci. 46, 238–244 (1957). https://doi.org/10.1007/BF03045973

Download citation

  • Received:

  • Issue Date:

  • DOI: https://doi.org/10.1007/BF03045973

Keywords

Search

Navigation