Cascade Wolff Rearrangement/Acylation: A Metal-Free and Eco-Friendly Approach for 4-Hydroxy-pyrazolo[3,4-b]pyridin-6-ones and N-Pyrazole Amides Synthesis from 5-Aminopyrazoles and α-Diazoketones

Abstract

A highly chemoselective cascade Wolff rearrangement/acylation reaction between 5-aminopyrazoles and diazo compounds has been developed. The protocol can facilitate the switchable synthesis of 4-hydroxy-pyrazolo[3,4-b]pyridin-6-ones and N-pyrazole amides with the merits of a broad substrate scope, high functional group compatibility, and green and sustainable performance manner. All reactions proceeded efficiently without any catalyst and additives (acid and base) and resulted in the release of benign N 2 , wherein diethyl carbonate served as a green benign solvent. Note pubs.acs.org/joc