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Superacid-catalysed arylation and rearrangement in 2-hydroxy-2,2′- biindan-1,1′,3,3′-tetrone and facile synthesis of 4-substituted phthalazinones
Published in -
Issue: 1
Pages: 5 - 10
2-Hydroxy-2,2′-biindan-1,1′,3,3′-tetrone 1 upon stirring with moderately activated and deactivated arenes in superacidic triflic acid (CF3SO3H, TfOH) medium produces arylated adducts 2-aryl-2,2′-biindan-1,1′,3,3′-tetrones 3 within 1-2 h. Prolonged stirring (12-24 h) of the same reaction mixture gives rearranged products 3-(aryl-1,3-indanedionylmethylene)isobenzofuranones 4 involving three types of regioselectivity. The arylated adducts 3 and rearranged products 4 undergo nucleophilic ring opening and condensation with hydrazine hydrate to produce 4-substituted mono- and diphthalazinones depending upon the reaction temperature.
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JournalJournal of Chemical Research
Open AccessNo