Facile synthetic protocols for perfluoroalkyl-substituted diazapentaphenes |
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| Authors: | Shigeyuki Yamada Shota Iwama Keita Kinoshita Takashi Yamazaki Toshio Kubota Tomoko Yajima |
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| Affiliation: | 1. Division of Applied Chemistry, Graduate School of Engineering, Tokyo University of Agriculture and Technology, 2-24-16 Nakamachi, Koganei 184-8588, Japan;2. Department of Biomolecular Functional Engineering, Ibaraki University, Nakanarusawa 4-12-1, Hitachi 316-8511, Japan;3. Department of Chemistry, Faculty of Science, Ochanomizu University, Otsuka, Bunkyo-ku, Tokyo 112-8610, Japan |
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| 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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| Keywords: | Fluoroalkylated compounds Nitrogen-containing heterocycles Polyaromatic hydrocarbons Benzyne insertion Friedel&ndash Crafts cyclization |
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