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.