Abstract 2-[(5-Methyl-1, 3, 4-oxadiazol-2-yl) methyl] benzenamine (15) was prepared in four steps from o-nitrophenyl-acetic acid, and treated with triethyl orthoformate in an attempt to prepare an oxadiazolobenzodiazepine. However, the resulting product was 13-(5-methyl-1, 3, 4-oxadiazol-2-yl)-5H-indolo [2, 1-b][1, 3] benzodiazepine monohydrate (16). Indolobenzodiazepine 16 is the first reported member of a novel ring system. Interesting ...