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
- Publication Type
- Journal contribution (peer reviewed)
- Authors
- Hajdok, S.; Conrad, J.; Leutbecher, H.; Strobel, S.; Schleid, T.; Beifuss, U.
- Year of publication
- 2009
- Published in
- J. Org. Chem.
- Editor
- American Chemical Society
- Band/Volume
- 74/19
- DOI
- 10.1021/jo9011915
- Page (from - to)
- 7230-7237
The laccase-catalyzed reaction between catechols and heterocyclic 1,3-dicarbonyls (pyridinones, quinolinones, thiocoumarins) using aerial oxygen as the oxidant delivers benzofuropyridinones, e.g. I, benzofuroquinolinones, e.g. II [X = NH], and thiocoumestans, e.g. II [X = S], in a simple fashion, highly regioselectively with yields ranging from 55 to 98%. With barbituric acid derivs. the exclusive formation of dispiropyrimidinone derivs. 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 anal.