A NEW SHORT WAY TO FUROCOUMARINS

Citation
Vf. Traven et al., A NEW SHORT WAY TO FUROCOUMARINS, Heterocyclic communications, 2(4), 1996, pp. 345-354
Citations number
20
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
ISSN journal
07930283
Volume
2
Issue
4
Year of publication
1996
Pages
345 - 354
Database
ISI
SICI code
0793-0283(1996)2:4<345:ANSWTF>2.0.ZU;2-T
Abstract
The Fries rearrangement of hydroxycoumarin chloroacetates provides a n ew short way to furocoumarins. 7-Hydroxycoumarin chloroacetates have b een transformed in the presence of AlCl3 into the proper dihydrofuro[2 ,3-h]coumarin-9-ones in high yields. 8-Substituted-7-hydroxycoumarin c hloroacetates undergo into dihydrofuro[2,3-g]coumarin-6-ones in the pr esence of AlCl3. 4-Hydroxycoumarin chloroacetate has been transformed into the dihydrofuro[2,3-c]coumarin-3-one in the same conditions. Redu ction of all dihydrofurocoumarinones followed by dehydration provide t he proper furocoumarins in good yields. This new way to furocoumarins is mostly suitable for angelicin derivatives synthesis. All new coumar in derivatives have been characterised by NMR and mass spectra.