10.1016/S0040-4039(02)01756-2
The research focuses on the facile synthesis of a selectively protected triazamacrocycle, which is of synthetic interest due to its unique binding properties with metal ions and potential applications in biomedical fields such as magnetic resonance imaging and radioimmunotherapy. The study reports a method for the regioselective N-functionalization of azamacrocycles, which is scarce in the literature. The synthesis involves the selective homologation of 1,7-diaminoheptane with the novel reagent N-(2-nitrobenzenesulfonyl)aziridine, followed by a series of reactions to afford a selectively protected 14-membered triazamacrocyclic ring. Key chemicals used in the process include N-(2-nitrobenzenesulfonyl)aziridine, N-tert-butoxycarbonyl anhydride, diethylphosphoryl chloride (DEPCl), trifluoroacetic acid (TFA), bromoacetyl bromide, and potassium carbonate (K2CO3). The conclusion of the research is the development of a method for the synthesis of selectively protected triazamacrocycles, allowing for functionalization at any ring nitrogen atom, which is a significant advancement for the synthesis of larger or smaller sized azamacrocyclic rings.