American Chemical Society
jo070564m_si_003.cif (12.32 kB)

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

Download (12.32 kB)
posted on 2007-07-20, 00:00 authored by Hiroyuki Suzuki, Norio Sakai, Ryohei Iwahara, Takayuki Fujiwaka, Mitsunobu Satoh, Akikazu Kakehi, Takeo Konakahara
In this study, fluorine-containing pentasubstituted pyridine derivatives 9am 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 11ak were synthesized in excellent yields by the subsequent base-promoted intramolecular skeletal transformation of the resulting pyridine derivatives 10ak.