Synthesis and Functionalization of 5,7-Dinitroquinoline and Its N-Oxide

An efficient method was developed for the synthesis of 5,7-dinitroquinoline and its N-oxide. The reactions of these compounds with either thiols or sodium azide resulted in the regiospecific substitution of 5-NO2 group and the formation of previously unknown quinoline derivatives. The 5-azido derivatives underwent reactions with 1,3-dicarbonyl compounds and, depending on the nature of reagent, afforded either 5-(1,2,3-triazol)-1-yl- or 5-amino-7-nitroquinolines, which have been previously inaccessible by using other methods.