Synthesis of novel crown ethers .1. Coumestan and coumestan analog derivatives of crown ethers

Abstract

The presented ethylenedioxy compounds 5a, 5d, 6a and 6c are examples of novel cyclic ethers, while macrocyclic polyethers represent new crown ether analogues. New coumestan-crowns 5a-f, derivatives of 6, 7-dihydroxy-3, 4-dihydro-2H-dibenzofuran and 6, 7-dihydroxy-3, 3-dimethyl-3, 4-dihydro-2H-dibenzofuran-1-one 6a-e were synthesized from the corresponding o-dihydroxy compounds 3a-b, 4a-b and ditosylates or dichlorides of di- or triethylene glycol in the presence of K2CO3, in DMF/H2O (15/1) solutions at 65-75 degrees C for 35 hours. The structure of the macrocyclic ethers obtained were confirmed by H-1-NMR, C-13-NMR, IR spectra and elemental analyses.