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 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.
Hajdok
Szilvia
S
Bioorganische Chemie, Institut für Chemie, Universität Hohenheim, Garbenstrasse 30, D-70599 Stuttgart, Germany.
Conrad
Jürgen
J
Leutbecher
Heiko
H
Strobel
Sabine
S
Schleid
Thomas
T
Beifuss
Uwe
U
D000364:Agaricus / Q000201:enzymology; D001463:Barbiturates / Q000138:chemical synthesis / Q000737:chemistry*; D002384:Catalysis; D002396:Catechols / Q000737:chemistry*; D003374:Coumarins / Q000737:chemistry*; D018360:Crystallography, X-Ray; D006571:Heterocyclic Compounds / Q000737:chemistry; D042845:Laccase / Q000737:chemistry / Q000378:metabolism*; D009682:Magnetic Resonance Spectroscopy; D008958:Models, Molecular; D015394:Molecular Structure; D010084:Oxidation-Reduction; D010100:Oxygen / Q000737:chemistry; D011728:Pyridones / Q000737:chemistry*; D015363:Quinolones / Q000737:chemistry*
D001463:Barbiturates; D002396:Catechols; D003374:Coumarins; D006571:Heterocyclic Compounds; D011728:Pyridones; D015363:Quinolones; D042845:Laccase; D010100:Oxygen; C032232:barbituric acid