Abstract
Bis(bromobenzyl)derivatives of cyclen and cyclam obtained according to previously described procedures were introduced in a palladium-catalyzed reaction with 1,3bis(aminomethyl)adamantane and 1,3-bis(2-aminoethyl)adamantane to produce macrobicycles in moderate yields. The formation of tricyclic cyclodimers was observed in many cases. Tetrabenzyl derivatives of cyclen and cyclam were synthesized from the corresponding dibenzyl derivatives and reacted with 1,3-bis(2-aminoethyl)adamantane to give macrobicyclic products in similar yields.
Highlights
Macropolycyclic compounds containing cyclen (1, 4, 7, 10-tetraazacyclododecane) and cyclam (1, 4, 8, 11-tetraazacyclotetradecane) moieties have been known for the last decades and can be classified in different classes of topology: macrobicyclic and macrotricyclic cryptands, macropolycycles of cylindrical shape, macropolycycles incorporating other macrocyclic structures
In our recent communication[31] we showed that the presence of two additional substituents in the tetraazamacrocyclyc fragment can dramatically change the macrocyclization path leading to preferable formation of macrotricyclic cryptands rather than to macrobicycles
The results suggest that cyclen and cyclam derivatives with m-bromobenzyl substituent are more suitable for the macrocyclization with adamantanediamines 13a,b with a rigid and bulky central fragment
Summary
Macropolycyclic compounds containing cyclen (1, 4, 7, 10-tetraazacyclododecane) and cyclam (1, 4, 8, 11-tetraazacyclotetradecane) moieties have been known for the last decades and can be classified in different classes of topology: macrobicyclic and macrotricyclic cryptands, macropolycycles of cylindrical shape, macropolycycles incorporating other macrocyclic structures.
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