Synthesis, characterization, and crystal structure of 2-(2-azidophenyl)-3-oxo-3H-indole 1-oxide

An attempt to explore the reactivity of the nitro group in the presence of gold catalysis in comparison to the azide group yielded intriguing results. Surprisingly, only the nitro group exhibited reactivity, ultimately giving rise to the formation of the title isatogen, C14H8N4O2. In the crystal structure, weak C-H center dot center dot center dot O hydrogen bonds and pi-pi stacking interactions link the molecules. The structure exhibits disorder of the molecule.