To achieve this goal, we envisioned a skeletal editing tool. The field of skeletal editing has been rapidly expanding; although most studies focus on altering skeletal frameworks (Figure ). Methods for the direct exchange of atoms constituting the core of nitrogen heterocycles without changing their structural topography (i.e., atom transmutation) remain scarce, although reports toward this goal are emerging (Figure ). In 2022, Burns et al. reported a sequential nitrogen insertion/carbon deletion reaction of aryl azides to achieve a C → N atom transmutation. In 2023, Levin et al. reported a similar, ipso-selective C → N atom transmutation. In 2023, Morandi et al. published a method that enabled skeletal metalation of lactams, facilitating a 12 C → C isotopic skeletal edit. Interest has continued to grow in the paradigm of isotopic labeling of the skeletons of molecules. For example, in 2023, Levin et al. disclosed a facile synthesis of C core-labeled phenols (Figure ) from a precursor bis-vinyl dibromide. Herein, we report a method that accomplishes a direct 14 N → N atom swap in a wide variety of nitrogen heteroaromatics using an accessible, easy to prepare N-enriched aspartatederived diester. Key to this transformation is a low-temperature triflylation of the heterocyclic nitrogen atom, followed by an aspartate mediated ring-opening/ring-closure sequence to yield an isolable N-succinyl intermediate where the nitrogen in the ring has been swapped. Elimination of the succinyl group as fumarate or maleate in situ unveils the isotopically labeled heterocycle. Importantly, this transformation takes place rapidly under mild conditions on a diverse library of heteroaromatics in excellent chemical yields and generally useful levels of isotopic enrichment. This method directly enriches nitrogen heteroaromatics in complex molecules with N using a readily available N source enabling high-sensitivity, rapid magnetic resonance experimentation in a broader area of chemical space to enable impact in drug development, materials science, molecular imaging, and molecular biology.