Investigations on the synthesis and chemiluminescenceof novel 2-coumaranones - II

International audienceThe optimized one-pot synthesis of 16 new 2-coumaranones containing a carbamate side-chain is described. Furthermore, the quantum yields for the base-activated chemiluminescence in the presence of oxygen was determined for all compounds, with a maximum of 5.9 ± 0.1 x 10-2 E mol–1, and the application of these compounds as substitutes for usual bioluminescent and chemiluminescent reagents in bioassays is anticipated. A preliminary mechanistic pathway is also suggested, making use of recent developments regarding aspects of organic chemiluminescence, in agreement with both experimental and theoretical data available on the induced 1,2-dioxetanone decomposition as well as with the high efficiency of this reaction