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.
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.
Suzuki
Hiroyuki
H
Department of Pure and Applied Chemistry, Faculty of Science and Technology, Tokyo University of Science (RIKADAI), Noda, Chiba 278-8510, Japan.
Sakai
Norio
N
Iwahara
Ryohei
R
Fujiwaka
Takayuki
T
Satoh
Mitsunobu
M
Kakehi
Akikazu
A
Konakahara
Takeo
T
D000838:Anions; D003500:Cyclization; D005466:Fluorocarbons / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D009287:Naphthyridines / Q000138:chemical synthesis* / Q000737:chemistry; D011725:Pyridines / Q000737:chemistry*; D016339:Spectrometry, Mass, Fast Atom Bombardment
D000838:Anions; D005466:Fluorocarbons; D009287:Naphthyridines; D011725:Pyridines