Synthesis of a novel macrocyclic ligand containing bipyridine units

The 6-hydroxymethyl-6'-tetrahydropyranyloxymethyl-2, 2'-bipyridine (2) was synthesized by the reaction of 6,6'-dihydroxymethyl-2, 2'-bipyridine (1) with 3, 4-dihydropyran (DHP). 6-Tetrahydropyranyloxymethyl-6'-iodomethyl-2, 2'-bipyridine (5) was obtained from mesylate and iodizating reaction of compound 2. The coupling of 2 and 5 followed by hydrolysis gave bis(6'-hydroxymethyl-2,2'-bipyridine-6-methyl) ether (7). The macrocyclic ligand 8 was obtained by treating 7 and 6,6'-dibromomethyl-2,2'-bipyridine. The synthetic conditions of the intermediate 2 and macocyclic ligand 8 were discussed. © 2000 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim