Unexpected dearomatization of N-protected 5-aminopyrazoles at ambient temperature: a simple route to highly functionalized pyrazolines

Abstract

We present a new strategy for the dearomatized hydroxylation of 5-aminopyrazoles using a hypervalent iodine reagent at room temperature. This method produces a series of 4-hydroxy-5-iminopyrazolines with good to excellent yields within 2 hours. Additionally, we demonstrate a domino reaction for the synthesis of 4-hydroxy-pyrazolones. Mechanistic studies indicate that the dearomatization proceeds through a cationic intermediate.