General Approach to Synthesis of 3-Amino-4-arylquinolin-2(1H)-ones and 3-Amino-4-arylquinoline-2(1H)-thiones Based on Isocyanates, Isothiocyanates and 1-(2-Aryl-2-oxolethyl)pyridin-1-ium Iodides

A general approach was developed to the synthesis of 3-amino-4-arylquinolin-2(1H)-ones and 3-amino-4-arylquinoline-2(1H)-thiones, based on simple and readily available reagents, with good overall yields of up to 76%. A broad variety of aryl and heteroaryl substituents introduced at the C-4 position of the quinoline system was achieved. The route can also be used for the synthesis of 4-alkyl derivatives, as shown in the example of 4-methylquinolines. Solutions of some synthesized compounds emit in the blue-violet region of the visible spectrum with fluorescence quantum yields of up to 0.33 upon UV irradiation.