The synthesis of azamacrocycles in which thering nitrogens are regioselectively functionalized is described. An organozinc palladium(0)-catalyzed coupling withan appropriately functionalized bromopyridine generated akey intermediate, which was transformed in two steps to adesired precursor and subjected to an intramolecular N-alkylation to effect a macrocyclization affording selectivelyprotected azamacrocycles 1−3.