A Sustainable Synthesis of Asymmetric Phenazines and Phenoxazinones Mediated by CotA-Laccase

Ana Catarina Sousa, M. Conceição Oliveira, Lígia O. Martins, M. Paula Robalo

Research output: Contribution to journalArticle

7 Citations (Scopus)

Abstract

An efficient and sustainable one-step procedure for the synthesis of new asymmetric phenazines and phenoxazinones from commercially available ortho-substituted diamines and ortho-substituted hydroxyamines is reported. In this study we have expanded the substrate scope of CotA-laccase-catalyzed aerobic oxidations through the use of aromatic amines presenting variable functional groups, including N-substitution, contributing to the rational synthesis of different heterocyclic scaffolds. The transformations proceed smoothly through a cascade of oxidative reactions to the benzoquinonediimine intermediates followed by nucleophilic addition, intramolecular cyclization and aromatization, all performed in mild conditions. (Figure presented.).

Original languageEnglish
Pages (from-to)575-583
Number of pages9
JournalAdvanced Synthesis and Catalysis
Volume360
Issue number3
DOIs
Publication statusPublished - 1 Feb 2018

Keywords

  • Biocatalysis
  • Homocoupling reactions
  • Laccase
  • Nitrogen heterocycles
  • Oxidation

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