Easy Access to 3,8-Diaryldifurano[2,3-a:2‘,3‘-f]naphthalenes. A New Extended Aromatic System
- 15 November 2000
- journal article
- research article
- Published by American Chemical Society (ACS) in The Journal of Organic Chemistry
- Vol. 65 (25) , 8783-8785
- https://doi.org/10.1021/jo005646o
Abstract
3,8-Diaryldifurano[2,3-a:2‘,3‘-f]naphthalenes were prepared in two simple steps. First, 1,5-dihydroxynaphthalene and 1-aryl-2-bromodecan-1-ones were condensed to the corresponding naphthalene 1,5-diethers. Second, these intermediates were cyclized using methanesulfonic acid in methylene chloride. Seven examples are given, three of which are doubly substituted with octyl chains 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).Keywords
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