title: One-pot synthesis of 3-fluoro-4-(trifluoromethyl)quinolines from pentafluoropropen-2-ol and their molecular modification.
abstract: Pentafluoropropen-2-ol (PFP) was prepared by the reaction of hexafluoroacetone (HFA) with Mg/TMSCl. The one-pot tandem sequential reactions of PFP via Mannich addition with aldimines followed by Friedel-Crafts cyclization and aromatization afforded the title quinolines. A variety of corresponding 3-substituted quinolines were derived from the title quinoline by nucleophilic substitution of 3-fluorine with nucleophiles. A defluorinative transformation of the 4-trifluoromethyl group of the title quinoline with hydrazine afforded pyrazoloquinoline.
authors.affiliation: Department of Applied Chemistry, Faculty of Engineering, Okayama University, 3-1-1 Tsushimanaka, Okayama 700-8530, Japan.
authors.forename: Tsuyoshi
authors.initials: T
authors.lastname: Hosokawa
authors.forename: Akemi
authors.initials: A
authors.lastname: Matsumura
authors.forename: Toshimasa
authors.initials: T
authors.lastname: Katagiri
authors.forename: Kenji
authors.initials: K
authors.lastname: Uneyama
mesh_terms: D000475:Alkenes / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D011804:Quinolines / Q000138:chemical synthesis* / Q000737:chemistry; D021241:Spectrometry, Mass, Electrospray Ionization; D013055:Spectrophotometry, Infrared
chemical_list: D000475:Alkenes; D011804:Quinolines; C013658:propylene