ol9b02206_si_002.pdf (5.37 MB)
One-Pot Highly Regioselective Synthesis of α‑Ketoamide N‑Arylpyrazoles from Secondary β‑Enamino Diketones
journal contribution
posted on 2019-07-29, 11:04 authored by Julia Poletto, Gessica M. Ribeiro, Michael J. V. da Silva, Andrey P. Jacomini, Ernani A. Basso, Davi F. Back, Sidnei Moura, Fernanda A. RosaAn
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.