ORGANOPHOSPHORUS CHEMISTRY .25. THE UTILIZATION OF WITTIG REAGENTS INLACTONE RING FORMATION - APPLICATION TO THE SYNTHESIS OF LINEAR FUROCOUMARINS AND PYRANOCOUMARINS

Authors
ATTA SMS HAFEZ TS MAHRAN MR
Citation
Sms. Atta et al., ORGANOPHOSPHORUS CHEMISTRY .25. THE UTILIZATION OF WITTIG REAGENTS INLACTONE RING FORMATION - APPLICATION TO THE SYNTHESIS OF LINEAR FUROCOUMARINS AND PYRANOCOUMARINS, Phosphorus, sulfur and silicon and the related elements, 80(1-4), 1993, pp. 109-116
Citations number
23
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Phosphorus, sulfur and silicon and the related elements → ACNP
ISSN journal
10426507
Volume
80
Issue
1-4
Year of publication
1993
Pages
109 - 116
Database
ISI
SICI code
1042-6507(1993)80:1-4<109:OC.TUO>2.0.ZU;2-3
Abstract
A new and improved method for the preparation of linear furocoumarins (7a,b) and pyranocoumarins (10a,b) in high yields, is described. It de pends upon reacting ylid-phosphoranes (5) with suitably substituted be nzofuran-, (3) or the benzo-gamma-pyrone-(4) moiety. Formation of the target compounds (7 and 10) is assumed to proceed via lactonization of cis alkyl alpha-hydroxycinnamate intermediates of types 6 and 9, resp ectively. The trans analogues 8 do not lactonize to 10 even upon heati ng in boiling toluene. The new compounds have been characterized by th eir spectroscopic data (IR, PMR, C-13 NMR) and elementary analyses.