Synthesis of some tetrahydronaphthyl- and flavanyl-coumarins

Abstract

The synthesis is described of a number of 3-[3-(p-substituted phenyl)-1,2,3,4-tetrahydro-1-naphthyl]-4-hydroxycoumarins (7) and 3-(4′-substituted flavan-4-yl)-4-hydroxycoumarins (17), many of which show outstanding activity as anticoagulants against both Warfarin-resistant rats. The final stage in the syntheses involves the reaction of either 3-(p-substituted phenyl)-1,2,3,4-tetrahydro-1-naphthols (6) or 4′-substituted flavan-4-ols (16) with 4-hydroxycoumarin to give the products (7) or (17), respectively, as mixtures of stereoisomers.