Unified Access to Pyrimidines and Quinazolines Enabled by N-N Cleaving Carbon Atom Insertion.

ABSTRACT: Given the ubiquity of heterocycles in biologically active molecules, transformations with the capacity to modify such molecular skeletons with modularity remain highly desirable. Ring expansions that enable interconversion of privileged heterocyclic motifs are especially interesting in this regard. As such, the known mechanisms for ring expansion and contraction determine the classes of heterocycle amenable to skeletal editing. Herein, we report a reaction that selectively cleaves the N-N bond of pyrazole and indazole cores to afford pyrimidines and quinazolines, respectively. This chlorodiazirine-mediated reaction provides a unified route to a related pair of heterocycles that are otherwise typically prepared by divergent approaches. Mechanistic experiments and DFT calculations support a

SUBMITTER: Hyland EE 

PROVIDER: S-EPMC9619406 | biostudies-literature | 2022 Oct

REPOSITORIES: biostudies-literature