Monatshefte für Chemie / Chemical Monthly

, Volume 112, Issue 1, pp 119–124 | Cite as

A convenient synthesis of linear pyranocoumarins. Xanthyletin and 3-Phenylxanthyletin

  • V. K. Ahluwalia
  • K. Bhat
  • Chandra Prakash
  • Manjula Khanna
Organic Chemistry and Biochemistry

Abstract

A convenient synthesis of linear pyranocoumarins, viz., 8,8-dimethyl-2H,8H-benzo[1,2-b; 5,4-b]dipyran-2-one (xanthyletin,1) and 8,8-dimethyl-3-phenyl-2H,8H-benzo[1,2-b; 5,4-b]dipyran-2-one (3-phenylxanthyletin,2) is described. The key steps are blocking the 8-position of appropriate 7-hydroxy-2H-1-benzopyran-2-one derivatives with iodine and 1,1-dimethyl-2-propynylation followed by cyclisation.

Keywords

Pyranocoumarins Xanthyletin derivatives 

Ein einfacher Syntheseweg zu linearen Pyranocumarinen. Xanthyletin und 3-Phenylxanthyletin

Zusammenfassung

Es wird ein vorteilhafter Weg zur Synthese von linearen Pyranocumarinen am Beispiel von Xanthyletin und 3-Phenylxanthyletin gezeigt. Das Syntheseprinzip besteht in einer Blockierung der 8-Position des entsprechenden 7-Hydroxy-2H-1-benzopyran-2-ons mit Jod und einer 1,1-Dimethyl-2-propinylierung mit nachfolgender Cyclisierung.

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Copyright information

© Springer-Verlag 1981

Authors and Affiliations

  • V. K. Ahluwalia
    • 1
  • K. Bhat
    • 1
  • Chandra Prakash
    • 1
  • Manjula Khanna
    • 1
  1. 1.Department of ChemistryUniversity of DelhiDelhi-7India

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