¹⁴N to ¹⁵N Isotopic Exchange of Nitrogen Heteroaromatics through Skeletal Editing.

ABSTRACT: The selective modification of nitrogen heteroaromatics enables the development of new chemical tools and accelerates drug discovery. While methods that focus on expanding or contracting the skeletal structures of heteroaromatics are emerging, methods for the direct exchange of single core atoms remain limited. Here, we present a method for ¹⁴N → ¹⁵N isotopic exchange for several aromatic nitrogen heterocycles. This nitrogen isotope transmutation occurs through activation of the heteroaromatic substrate by triflylation of a nitrogen atom, followed by a ring-opening/ring-closure sequence mediated by ¹⁵N-aspartate to effect the isotopic exchange of the nitrogen atom. Key to the success of this transformation is the formation of an isolable ¹⁵N-succi

SUBMITTER: Bartholomew GL 

PROVIDER: S-EPMC11646074 | biostudies-literature | 2024 Feb

REPOSITORIES: biostudies-literature