title: Ring-fluorinated isoquinoline and quinoline synthesis: intramolecular cyclization of o-cyano- and o-isocyano-beta,beta-difluorostyrenes.
abstract: o-Cyano-beta,beta-difluorostyrenes react with organolithiums selectively at the cyano carbon to generate the corresponding sp(2) nitrogen anions, which in turn undergo intramolecular replacement of the vinylic fluorine to afford 3-fluoroisoquinolines. Similarly, the reaction of beta,beta-difluoro-o-isocyanostyrenes with organomagnesiums or -lithiums generates the corresponding sp(2) carbanions on the isocyano carbon. Subsequent cyclization via substitution of the fluorine leads to 3-fluoroquinolines. [reaction: see text]
authors.affiliation: Department of Chemistry, Graduate School of Science, The University of Tokyo, Hongo, Bunkyo-ku, Tokyo 113-0033, Japan. junji@chem.s.u-tokyo.ac.jp
authors.forename: Junji
authors.initials: J
authors.lastname: Ichikawa
authors.forename: Yukinori
authors.initials: Y
authors.lastname: Wada
authors.forename: Hiroyuki
authors.initials: H
authors.lastname: Miyazaki
authors.forename: Takashi
authors.initials: T
authors.lastname: Mori
authors.forename: Hiroyuki
authors.initials: H
authors.lastname: Kuroki
mesh_terms: D003500:Cyclization; D006845:Hydrocarbons, Fluorinated / Q000138:chemical synthesis*; D007546:Isoquinolines / Q000138:chemical synthesis*; D009570:Nitriles / Q000737:chemistry*; D011804:Quinolines / Q000138:chemical synthesis*; D013343:Styrenes / Q000737:chemistry*
chemical_list: D006845:Hydrocarbons, Fluorinated; D007546:Isoquinolines; D009570:Nitriles; D011804:Quinolines; D013343:Styrenes