A three-component synthesis of beta-alkoxy-beta-keto-enamides-flexible precursors for 4-hydroxypyridine derivatives and their palladium-catalysed reactions

作者：Lechel Tilman; Dash Jyotirmayee; Eidamshaus Christian; Bruedgam Irene; Lentz Dieter; Reissig Hans Ulrich^*

来源：Organic and Biomolecular Chemistry, 2010, 8(13): 3007-3014.

DOI：10.1039/b925468d

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.

• 出版日期2010