Abstract
Novel syntheses of 13,14-bis(perfluoroalkyl)-substituted 5,8-diazapentaphene derivatives were realized by such a facile two-step protocol as consecutive benzyne insertion into C(O)–NH bonds of p-phenylene-bis(perfluoroalkanamides), followed by Friedel–Crafts type cyclization reaction, yielding the corresponding title compounds especially for the case of Rf=CF3 or C2F5. Additionally, an alternative approach based on condensation of cyclohexane-1,4-dione with (o-aminophenyl) perfluoroalkyl ketones, followed by dehydrogenation enabled us to effectively access to the same final products in better yields.
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