REGIOSELECTIVE INTRODUCTION OF CARBON-3 SUBSTITUENTS TO 5-ALKYL-7-METHOXY-2-PHENYLBENZO[B]FURANS - SYNTHESIS OF A NOVEL ADENOSINE-A1-RECEPTOR LIGAND AND ITS DERIVATIVES

By maintaining the balance between the electronic requirements, the stereochemical restrictions as well as the kinetic and thermodynamic factors, the unprecedented regioselective electrophilic aromatic substitution of formyl and nitro groups to carbon-3 of 5-alkyl-7-methoxy-2-phenylbenzo[b]furans have been achieved. Subsequent transformation of the resulting formyl group into methyl, hydroxymethyl, 1-hydroxyethyl, and cyano groups are also described.