Formation of a Hydrogen-Bonded Barbiturate [2]-Rotaxane

Interlocked structures containing the classic Hamilton barbiturate binding motif comprising two 2,6-diamidopyridine units are reported for the first time. Stable [2]-rotaxanes can be accessed either through hydrogen-bonded preorganization by a barbiturate thread followed by a Cu+-catalyzed “click” stoppering reaction or by a Cu2+-mediated Glaser homocoupling reaction.