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Two approaches to the synthesis of polyazamacrocycles containing two biphenyl and two polyamine moieties are described. The first route comprises the synthesis of N,N'bis(bromobiphenyl) substituted diand poly-amines by the reactions of 2.2-3 equivalents of 4,4'or 3,3'-dibromobiphenyls with corresponding diand polyamines followed by the reaction with a second molecule of the amine. The second approach includes the synthesis of bis(polyamine) substituted biphenyls by the reactions of 4,4'or 3,3'-dibromobiphenyls with four equivalents of diand poly-amines with subsequent reaction of these in situ prepared intermediates with dibromobiphenyls. The yields of target macrocycles obtained according to two routes are compared and the advantage of the approach via bis(polyamine) substituted biphenyls in the majority of cases is established. Side products, when formed in all reactions, were analyzed.

Pd-catalyzed amination of dibromobiphenyls in the synthesis of macrocycles comprising two biphenyl and two polyamine moieties