M. Jorgensen et al., Easy access to 3,8-diaryldifurano[2,3-a : 2 ',3 '-f]naphthalenes. A new extended aromatic system, J ORG CHEM, 65(25), 2000, pp. 8783-8785
3,8-Diaryldifurano[2,3-a:2',3'-f]naphthalenes were prepared in two simple s
teps. First, 1,5-dihydroxynaphthalene and 1-aryl-2-bromodecan- 1-ones were
condensed to the corresponding naphthalene 1,5-diethers. Second, these inte
rmediates were cyclized using methanesulfonic acid in methylene chloride. S
even examples are given, three of which are doubly substituted with octyl c
hains to enhance the solubility. This increased solubility allowed further
modification of the 3,8-aryl groups to attach electron-withdrawing groups (
formyl, nitrile, dicyanovinyl, and benzoyl).