Halogenations of 3-Aryl-1 H -pyrazol-5-amines
Synthesis(2022)
Abstract
A direct C-H halogenation of 3-aryl-1H-pyrazol-5-amines with NXS (X = Br, I, Cl) as cheap and safe halogenating reagents at room temperature has been developed. This transformation provides an effective metal-free protocol towards the synthesis of novel 4-halogenated pyrazole derivatives with moderate to excellent yields. The method represents simple and mild reaction conditions, broad substrate scope as well as gram-scale synthesis. The utility of this procedure is established by further transformations of the 4-halogenated products. Mechanism studies show that DMSO plays a dual role of catalyst and solvent.
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Key words
halogenation,metal-free,pyrazol-5-amine,synthesis,4-halogenopyrazole,N -halogenosuccinimides,dimethyl sulfoxide
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