Synthesis of fluorescent hydroxyl naphthalene-1,4-dione derivatives by a three-component reaction in water

摘要

An efficient one-pot synthesis of fluorescent hydroxyl naphthalene-1,4-dione derivatives by a simple atom-economical and three-component reaction of 2- hydroxynaphthalene-1,4-dione, aromatic aldehydes and heterocyclic or carbocyclic amines in the presence of a catalytic amount of InCl3 in refluxing water is reported. The structures of the compounds were confirmed by IR, ~1H NMR, ~(13)C NMR, and elemental analysis. UV- visible absorption coefficient, maximum wavelength and fluorescence emission wavelength were measured in methanol. The products were fluorescent in solution emitting at green light (546-560 nm). The advantages of this procedure are mild reaction conditions, high yields of products, operational simplicity and easy work-up procedures. The workup of these very clean reactions involves only a filtration and simple washing step with EtOH.