American Chemical Society
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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

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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.