title: A three-component synthesis of beta-alkoxy-beta-keto-enamides--flexible precursors for 4-hydroxypyridine derivatives and their palladium-catalysed reactions.
abstract: The flexible three-component reaction of lithiated alkoxyallenes with nitriles and carboxylic acids provided a series of highly functionalised beta-alkoxy-beta-ketoenamide derivatives. Upon base induced cyclisation and conversion to 4-pyridyl nonaflates various palladium-catalysed coupling reactions could be employed. The efficacy of this approach to functionalised pyridine derivatives was demonstrated by a fairly short route to a key intermediate suitable for a Glenvastatin synthesis. After Sonogashira couplings of alkynes with 4-pyridyl nonaflates subsequent cyclisations led to highly fluorescent [2,3c]furopyridine derivatives, whereas Suzuki reactions afforded 4-pyridyl stilbenes and by photocyclisation a highly substituted benzoisoquinoline derivative.
authors.affiliation: Institut für Chemie und Biochemie, Freie Universität Berlin, Takustr. 3, 14195, Berlin, Germany.
authors.forename: Tilman
authors.initials: T
authors.lastname: Lechel
authors.forename: Jyotirmayee
authors.initials: J
authors.lastname: Dash
authors.forename: Christian
authors.initials: C
authors.lastname: Eidamshaus
authors.forename: Irene
authors.initials: I
authors.lastname: Brüdgam
authors.forename: Dieter
authors.initials: D
authors.lastname: Lentz
authors.forename: Hans-Ulrich
authors.initials: HU
authors.lastname: Reissig