American Chemical Society
Browse
ol3c03904_si_002.zip (50.5 MB)

Silver-Catalyzed Skeletal Editing of Benzothiazol-2(3H)‑ones and 2‑Halogen-Substituted Benzothiazoles as a Rapid Single-Step Approach to Benzo[1,2,3]thiadiazoles

Download (50.5 MB)
dataset
posted on 2024-01-11, 14:14 authored by Jela Nociarová, Anisha Purkait, Róbert Gyepes, Peter Hrobárik
A facile silver­(I)-catalyzed reaction of benzothiazol-2­(3H)-ones with NaNO2, or using AgNO2 directly, enables a single-step transformation to the corresponding benzo­[1,2,3]­thiadiazoles in moderate to excellent yields, with wide functional group compatibility. It can also be performed in a one-pot manner from readily available 2-halobenzothiazoles. This intriguing transformation involving an atom replacement in the S,N-heteroarene ring thus provides rapid access to isobenzothiadiazoles (while avoiding the usage of unstable precursors) and also expands the toolbox of modern skeletal editing reactions.

History