Entry point into new trimeric and tetrameric imide-based macrocyclic esters derived from isophthaloyl dichloride and methyl 6-aminonicotinate

The reaction of isophthaloyl dichloride with methyl 6-aminonicotinate yields `3 + 3' and `4 + 4' imide-linked macrocycles with the former representing a new macrocycle class (trezimide). The role of 2-aminopyridine in imide hinge formation and ultimately macrocyclization is pivotal to this one-step synthetic route into cyclic triimides (trezimides) and tetraimides (tennimides).