title: Concise synthesis of multisubstituted isoquinolines from pyridines by regioselective Diels-Alder reactions of 2-silyl-3,4-pyridynes.
abstract: A four-step regioselective synthesis of multisubstituted isoquinoline derivatives from 3-bromopyridines was developed by the Diels-Alder (DA) reactions of 2-silyl-3,4-pyridynes with furans, followed by functional-group transformations. In particular, the silyl group at the C2-position of the 3,4-pyridynes played two important roles: firstly, it functioned as the directing group for the DA reaction, and secondly, it served to introduce diverse substituents at the C1-position of the isoquinolines by electrophilic ipso-substitution.
authors.affiliation: Graduate School of Pharmaceutical Sciences, Osaka University, 1-6 Yamadaoka, Suita, Osaka 565-0871 (Japan), Fax: (+81) 6-6879-8212, (+81) 6-6879-8210. ikawa@phs.osaka-u.ac.jp.
authors.forename: Takashi
authors.initials: T
authors.lastname: Ikawa
authors.forename: Hirohito
authors.initials: H
authors.lastname: Urata
authors.forename: Yutaka
authors.initials: Y
authors.lastname: Fukumoto
authors.forename: Yuta
authors.initials: Y
authors.lastname: Sumii
authors.forename: Tsuyoshi
authors.initials: T
authors.lastname: Nishiyama
authors.forename: Shuji
authors.initials: S
authors.lastname: Akai
mesh_terms: D061565:Cycloaddition Reaction; D005663:Furans / Q000737:chemistry; D007546:Isoquinolines / Q000138:chemical synthesis* / Q000737:chemistry; D011725:Pyridines / Q000737:chemistry*; D012821:Silanes / Q000737:chemistry
chemical_list: D005663:Furans; D007546:Isoquinolines; D011725:Pyridines; D012821:Silanes; C517741:3-bromopyridine
keywords: cycloaddition; furans; isoquinolines; pyridynes; silyl groups