Diazafluoranthene Derivatives via Diels-Alder Reaction

Significance

Reported is the Diels-Alder reaction between 3,6-disubstituted 1,2,4,5-tetrazines and either acenaphthylene or 3,8-dimethyl­acenaphthylene. The resulting diazafluoranthene products are mostly new compounds. Two equivalents of the tetrazine are required for the reaction, as one acts as the Diels-Alder partner, whilst the other acts as an oxidant. The scope of the tetrazines was well explored, with substitution to investigate a wide range of electronic effects, as well as heteroaromatics. Ultimately this chemistry could provide a route to diazacorannulene.