A New Synthetic Route to Heteroanthracenes

In this report, we describe the synthesis of 2,3,4a,6,7,8a,9,10‐octaaza‐4,8‐dioxo‐3,4,4a,7,8,8a,9,9a,10,10a‐decahydroanthracene, an octaaza derivative of reduced anthracene, through the reaction of glyoxal bis(nitrosemicarbazone) with glyoxal bis(hydrazone) in aqueous medium at 70 °C as well as by the hydrolytic decomposition of glyoxal bis(nitrosemicarbazone) in aqueous medium at 70 °C in a one‐pot transformation. The structure of the resultant compound was confirmed by physicochemical analytical methods and X‐ray diffraction. We also obtained the first representative of the cyclic monohydrazone dimer 1,2,4,5,8,9,11,12‐octaazacyclotetradeca‐5,7,12,14‐tetraene‐3,10‐dione, which exists as lactam and lactim tautomers, through the reaction of glyoxal bis(nitrosemicarbazone) with glyoxal bis(hydrazone) in alkaline aqueous medium.