Access to polysubstituted naphthalenes and anthracenes via a retro-Diels–Alder reaction

Article abstract of DOI:10.1016/j.tet.2017.07.058

Naphthalene and anthracene nuclei are present in several natural and synthetic compounds. Due to their unique physical and chemical properties, access to functionalized naphthalenes and anthracenes has attracted the attention of both synthetic and medicinal chemists over the decades. In this study, successive Diels–Alder/retro-Diels–Alder reactions of dimethyl 1,2,4,5-tetrazine-3,6-dicarboxylate with various bicyclic alkenes in one pot to yield naphthalene and anthracene derivatives are reported. Using anti- and syn-cyclotrimers derived from the cyclotrimerization of benzobarrelene as alkene partner enabled efficient synthesis of trinaphthylene.