122607-31-2Relevant academic research and scientific papers
3-(7-METHOXYCOUMARIN-3-CARBONYL)- AND 3-(7-DIMETHYLAMINOCOUMARIN-3-CARBONYL)-2-OXAZOLONES AS NEW FLUORESCENT LABELING REAGENTS FOR HIGH-PERFORMANCE LIQUID CHROMATOGRAPHY
Takadate, Akira,Yagashiro, Ichiro,Irikura, Mitsuru,Fujino, Hiroyuki,Goya, Shujiro
, p. 373 - 376 (2007/10/02)
3-(7-Methoxycoumarin-3-carbonyl)- and 3-(7-dimethylaminocoumarin-3-carbonyl)-2-oxazolones (IIa and IIb) were synthesized as fluorescent labeling reagents for high-performance liquid chromatography (HPLC).Treatment of 7-methoxy- and 7-dimethylaminocoumarin-3-carboxylic acids (Ia and Ib) with diphenyl 2-oxo-3-oxazolinylphosphonate in the presence of triethylamine in dichloromethane gave IIa and IIb in 45percent and 26percent yields, respectively.Compounds IIa and IIb reacted with primary and secondary amines at room temperature in chloroform to give the corresponding fluorescent 7-methoxy- and 7-dimethylamino-3-carboxamides (IIIa-i and IVa-i).A mixture of primary amines was labeled with IIa and chromatographed on a reversed-phase HPLC column (mobile phase: methanol-water) with a fluorescene detector.The detection limit of a test compound, benzylamine, was 19 fmol/100 μl by the use of IIa.Keywords - 3-(7-methoxycoumarin-3-carbonyl)-2-oxazolone; 3-(7-dimethylaminocoumarin-3-carbonyl)-2-oxazolone; labeling reagent; coumarin carboxamide; fluorescence-labeled amine; fluorescence quantum yield; synthesis; HPLC fluorescence detection
