SYNTHESIS OF MACROBICYCLES COMPRISING 2,7-DIAMINO-NAPHTHALENE MOIETY VIA PALLADIUM-CATALYZED AMINATION REACTION

An original synthetic approach to bismacrocyclic ligands bearing naphthalene moiety was developed. First, the macrocycles comprising 2,7diaminonaphthalene fragment were reacted with 2,7-dibromonaphthalene, 4,4'dibromobiphenyl or bromobenzyl bromide affording corresponding NN'bis(bromoaryl) or N,N'-bis(bromobenzyl) substituted macrocycles. Pd-catalyzed macrocyclization of these compounds with a wide range of di- and polyamines led to a series of new macrobicyclic ligands. The yields of the macrobicycles are strongly dependent on the nature of starting compounds, reaching 35% in some cases.