Laccase-mediated chemoselective C-4 arylation of 5-aminopyrazoles

PLoS One. 2024 Sep 18;19(9):e0308036. doi: 10.1371/journal.pone.0308036. eCollection 2024.

Abstract

Chemoselective arylation of 5-aminopyrazoles was performed through oxidative formation of orthoquinones from catechols catalyzed by Myceliophthora thermophila laccase (Novozym 51003), and subsequently nucleophilic attack of 5-aminopyrazole to the catechol intermediates. The C-4 arylated products were obtained under extremely mild conditions without the need for amine protection or halogenation of the substrates. From this method, 10 derivatives with moderate to good efficiency (42-94%) were prepared.

MeSH terms

  • Catalysis
  • Catechols / chemistry
  • Catechols / metabolism
  • Laccase* / chemistry
  • Laccase* / metabolism
  • Oxidation-Reduction
  • Pyrazoles* / chemistry
  • Sordariales / enzymology

Substances

  • Laccase
  • Pyrazoles
  • Catechols