Elsevier

Tetrahedron

Volume 2, Issues 3–4, May 1958, Pages 203-210
Tetrahedron

Synthesis of benzo-furan derivatives-I: Karanj ketone, karanjin and pongapin

https://doi.org/10.1016/0040-4020(58)88041-2Get rights and content

Abstract

A new method of preparing benzo-furan derivatives using substituted allyl phenols has been worked out. Ozonolysis of the allyl derivatives and subsequent ring closure of the resulting o-hydroxy-acetaldehydes by means of o-phosphoric acid give good yields of karanj ketone, karanjin, pongapin and the corresponding 2-methyl furanochromone. As an alternative route oxidation of the allyl phenol in two stages using performing acid followed by periodic acid has been successfully employed in the synthesis of karanjin.

References (18)

  • A. Rössing

    Ber. Dtsch. Chem. Ges.

    (1884)
    R.C. Elderfield
  • S. Rangaswami et al.

    Proc. Ind. Acad. Sci.

    (1939)
  • L.R. Row et al.

    Proc. Ind. Acad. Sci.

    (1951)
    L.R. Row et al.

    Proc. Ind. Acad. Sci.

    (1951)
  • R.L. Shriner et al.

    J. Amer. Chem. Soc.

    (1938)
  • C. Paal

    Ber. Dtsch. Chem. Ges.

    (1884)
  • W.J. Hale

    Ber. Dtsch. Chem. Ges.

    (1912)
  • T.R. Govindachari et al.

    J. Chem. Soc.

    (1957)
    W.J. Bowyer et al.

    J. Chem. Soc.

    (1957)
    J.N. Chatterjea

    Experientia

    (1956)
    J.N. Chatterjea et al.

    J. Ind. Chem. Soc.

    (1957)
  • T.R. Seshadri et al.

    Proc. Ind. Acad. Sci.

    (1941)
  • W. Baker et al.

    J. Chem. Soc.

    (1935)
There are more references available in the full text version of this article.

Cited by (22)

  • Asymmetric Synthesis of Concentricolide

    2015, European Journal of Organic Chemistry
  • Synthesis of psoralens and analogues

    1992, Journal of Photochemistry and Photobiology, B: Biology
  • Pyrans and Fused Pyrans: (ii) Reactivity

    1984, Comprehensive Heterocyclic Chemistry
View all citing articles on Scopus
View full text