Novel synthesis of 7-fluoro-8-(trifluoromethyl)- 1H-1,6-naphthyridin-4-one derivatives: intermolecular cyclization of an N-silyl-1-azaallyl anion with perfluoroalkene and subsequent intramolecular skeletal transformation of the resulting pentasubstituted pyridines |
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Authors: | Suzuki Hiroyuki Sakai Norio Iwahara Ryohei Fujiwaka Takayuki Satoh Mitsunobu Kakehi Akikazu Konakahara Takeo |
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Institution: | Department of Pure and Applied Chemistry, Faculty of Science and Technology, Tokyo University of Science (RIKADAI), Noda, Chiba 278-8510, Japan. |
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Abstract: | In this study, fluorine-containing pentasubstituted pyridine derivatives 9a-m were prepared regioselectively in good yields by the intermolecular cyclization of a variety of N-silyl-1-azaallylic anion intermediates 7, which were generated from a functionalized silane 5 and an aromatic/aliphatic nitrile 6 with perfluoroalkene 8. Also, 7-fluoro-8-(trifluoromethyl)-1H-1,6-naphthyridin-4-one derivatives 11a-k were synthesized in excellent yields by the subsequent base-promoted intramolecular skeletal transformation of the resulting pyridine derivatives 10a-k. |
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