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  • 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.

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.

The Journal of organic chemistry (2009-09-11)
Szilvia Hajdok, 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.

MATERIALS
Product Number
Brand
Product Description

Sigma-Aldrich
Sodium barbiturate, ≥97.0% (T)
Sigma-Aldrich
Barbituric acid, ReagentPlus®, 99%
Supelco
Barbituric acid, for spectrophotometric det. of cyanide, ≥99.5%