The Laccase-Catalyzed Domino Reaction between Catechols andHeterocyclic 1,3-Dicarbonyls and the Unambiguous Structure Elucidation ofthe Products by NMR Spectroscopy and X-ray Crystal Structure Analysis

摘要

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 yieldsranging from 55 to 98%. With barbituric acid derivatives the exclusive formation of dispiropyr-imidinone derivatives takes place. The unambiguous and complete structure elucidation of allreaction products has been achieved by means of NMR spectroscopic methods (HSQMBC andband-selective HMBC) as well as by X-ray crystal structure analysis.