Twin Annulation of Naphthalene via a 1,5-Naphthodiyne Synthon. New Syntheses of Chrysene and Dibenzochrysene

Article abstract of DOI:10.1021/jo00158a019

New, efficient syntheses of chrysene (1), dibenzochrysene (16), and derivatives are described that feature, as the key step, the formal cycloaddition between 1,5-naphthodiyne (3) and a heterocyclic diene (furan, pyrroles, isoindoles).Subsequent manipulation affords the arene in 26-49percent overall yield from commercially available 2,6-dibromo-1,5-dihydroxynaphthalene (5).The latter is easily converted to ditosylate 6, which, with phenyllithium, serves as a synthon for 3.