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One-Pot Highly Regioselective Synthesis of α‑Ketoamide N‑Arylpyrazoles from Secondary β‑Enamino Diketones

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journal contribution
posted on 29.07.2019, 11:04 by Julia Poletto, Gessica M. Ribeiro, Michael J. V. da Silva, Andrey P. Jacomini, Ernani A. Basso, Davi F. Back, Sidnei Moura, Fernanda A. Rosa
An efficient one-pot method is described for the highly regioselective synthesis of α-ketoamide N-arylpyrazoles from secondary β-enamino diketones. For this, the key intermediate, 4-acyl 3,5-dihydroxypyrrolone, was generated in situ and underwent bimolecular nucleophilic substitution at C-5 by arylhydrazine, with subsequent heterocyclization at the carbonyl carbon of the acyl group. This strategy allowed for regiochemical control of α-ketoamide N-arylpyrazoles from β-enamino diketones and arylhydrazines.