In this study, we harness the distinct reactivity of sulfenylnitrenes, which insert a single nitrogen atom to transform readily available pyrroles, indoles, and imidazoles into synthetically challenging pyrimidines, quinazolines, and triazines, respectively. Our additive-free method for skeletal editing employs easily accessible, benchtop-stable sulfenylnitrene precursors as a source of a single nitrogen atom. This chemical approach is compatible with free pyrroles, indoles, and imidazoles with diverse functional groups, including oxidation-sensitive functionalities like phenol and thioether. Additionally, this approach facilitates the selective incorporation of a single nitrogen atom into various natural products, amino acids, and pharmaceuticals. Furthermore, we have conducted mechanistic studies and explored regioselectivity outcomes through DFT calculations.
Supporting Information (SI)
Supporting Information for Publication, which includes the synthetic protocols, computational studies, and NMR spectra.