Literature DB >> 19739645

The laccase-catalyzed domino reaction between catechols and heterocyclic 1,3-dicarbonyls and the unambiguous structure elucidation of the products by NMR spectroscopy and X-ray crystal structure analysis.

Szilvia Hajdok1, Jürgen Conrad, Heiko Leutbecher, Sabine Strobel, Thomas Schleid, Uwe Beifuss.   

Abstract

The laccase-catalyzed reaction between catechols and heterocyclic 1,3-dicarbonyls (pyridinones, quinolinones, thiocoumarins) using aerial oxygen as the oxidant delivers benzofuropyridinones, benzofuroquinolinones, and thiocoumestans in a simple fashion, highly regioselectively with yields ranging from 55 to 98%. With barbituric acid derivatives the exclusive formation of dispiropyrimidinone derivatives takes place. The unambiguous and complete structure elucidation of all reaction products has been achieved by means of NMR spectroscopic methods (HSQMBC and band-selective HMBC) as well as by X-ray crystal structure analysis.

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Year:  2009        PMID: 19739645     DOI: 10.1021/jo9011915

Source DB:  PubMed          Journal:  J Org Chem        ISSN: 0022-3263            Impact factor:   4.354


  3 in total

Review 1.  Novel carbon-carbon bond formations for biocatalysis.

Authors:  Verena Resch; Joerg H Schrittwieser; Elina Siirola; Wolfgang Kroutil
Journal:  Curr Opin Biotechnol       Date:  2011-02-25       Impact factor: 9.740

2.  Efficient and sustainable laccase-catalyzed iodination of p-substituted phenols using KI as iodine source and aerial O2 as oxidant.

Authors:  Mark Sdahl; Jürgen Conrad; Christina Braunberger; Uwe Beifuss
Journal:  RSC Adv       Date:  2019-06-21       Impact factor: 4.036

Review 3.  Laccases: Versatile Biocatalysts for the Synthesis of Heterocyclic Cores.

Authors:  Ana Catarina Sousa; Lígia O Martins; M Paula Robalo
Journal:  Molecules       Date:  2021-06-18       Impact factor: 4.411

  3 in total

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