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A Sustainable Synthesis of Asymmetric Phenazines and Phenoxazinones Mediated by CotA‐Laccase
Advanced Synthesis & Catalysis ( IF 5.4 ) Pub Date : 2017-12-04 , DOI: 10.1002/adsc.201701228
Ana Catarina Sousa 1, 2 , M. Conceição Oliveira 2 , Lígia O. Martins 3 , M. Paula Robalo 1, 2
Affiliation  

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.

中文翻译:

CotA-漆酶介导的不对称吩嗪和苯恶嗪酮的可持续合成

据报道,从市售的邻位取代的二胺和邻位取代的羟胺合成新的不对称吩嗪类和吩恶嗪酮类的有效而可持续的一步步骤。在这项研究中,我们通过使用具有可变官能团(包括N取代基)的芳香胺,扩展了CotA-漆酶催化的好氧氧化的底物范围,有助于合理合成不同的杂环骨架。通过在苯并醌二亚胺中间体之间进行一系列的氧化反应,然后进行亲核加成,分子内环化和芳构化,所有这些反应均在温和的条件下顺利进行。
更新日期:2017-12-04
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