Design and microwave-assisted synthesis of naphtho[2,3-f]quinoline derivatives and their luminescent properties.

A sequential three-component reaction of an aromatic aldehyde with an equimolar amount of 2-aminoanthracene and cyclic 1,3-dicarbonyl compounds (such as tetronic acid, 5,5-dimethyl,3-cyclohexanedione, 1,3-indanedione, 3H-chromene-2,4-dione, quinoline-2,4(1H, 3H)-dione and barbituric acid) in acidic medium under microwave irradiation has been developed. In this one-pot reaction, a series of unusual fused heterocyclic compounds, naphtho[2,3-f]quinoline derivatives, were synthesized. This method has the advantages of operational simplicity, increased safety for small-scale fast synthesis, and minimal environmental impact. Most distinctively, this new class of naphtho[2,3-f]quinoline derivatives exhibit good luminescent properties in the ethanol solution, which can be used potentially as organic electroluminescent (EL) media.