Easy access to 3,8-diaryldifurano[2,3-a : 2 ',3 '-f]naphthalenes. A new extended aromatic system

Citation
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
Citations number
9
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
JOURNAL OF ORGANIC CHEMISTRY
ISSN journal
00223263 → ACNP
Volume
65
Issue
25
Year of publication
2000
Pages
8783 - 8785
Database
ISI
SICI code
0022-3263(200012)65:25<8783:EAT3:2>2.0.ZU;2-E
Abstract
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).