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A RhIII-catalysed ortho C-H amination of phenidones under mild conditions was developed using N-alkyl- O-benzoyl-hydroxylamines as aminating agents, and with a cyclic hydrazine moiety as a directing group, yields of up to 97 % and a high functional group tolerance were observed. This strategy offers an alternative route for the synthesis of amino analogues of the 5-lipoxygenase inhibitor phenidone, and the products are valuable for further functional group transformations. [ABSTRACT FROM AUTHOR]

A tandem one-pot Friedel-Crafts alkylation/double cyclization process to conveniently assemble diaryl-fused 2,8-dioxabicyclo[3.3.1]nonanes with aryl substituents at the C-1 position was developed. 2-Hydroxychalcones and naphthol derivatives reacted in refluxing toluene with ( D, L)-10-camphorsulfonic acid (CSA) as the catalyst. The transformation conveniently provided the corresponding 2,8-dioxabicyclo[3.3.1]nonanes fused with one phenyl and one naphthyl group in moderate to good yields, and various substitutions on both reaction partners were tolerated. More importantly, aryl- and aza-aryl-fused 2,8-dioxabicyclo[3.3.1]nonanes were prepared for the first time using this procedure. [ABSTRACT FROM AUTHOR]