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Synthesis of Benzoxazines by Heterogeneous Multicomponent Biochemo Multienzymes Cascade Reaction.

Elisabetta TomainoEliana CapecchiValentina UbertiniDavide PiccininoBruno Mattia BizzarriRaffaele Saladino
Published in: The Journal of organic chemistry (2024)
This work describes the possibility to combine multicomponent chemistry and multienzymes cascade transformations in a unique reactive framework to yield highly functionalized 1,4-benzoxazines under favorable heterogeneous conditions. The synthetic scheme involved the generation in situ of electrophilic reactive quinone intermediates of tyrosol esters catalyzed by lipase M and tyrosinase followed by nucleophilic 1,6-Michael addition of selected α-amino acid methyl esters, and successive intramolecular lactonization and aromatization processes. The immobilization of the multienzymes cascade on electroactive lignin nanoparticles improved the sustainability and recyclability of the overall system.
Keyphrases
  • amino acid
  • room temperature
  • molecularly imprinted
  • liquid chromatography