Lechel, Tilman ; Dash, Jyotirmayee ; Eidamshaus, Christian ; Brüdgam, Irene ; Lentz, Dieter ; Reissig, Hans-Ulrich (2010) A three-component synthesis of β-alkoxy-β-keto-enamides—flexible precursors for 4-hydroxypyridine derivatives and their palladium-catalysed reactions Organic and Biomolecular Chemistry, 8 (13). p. 3007. ISSN 1477-0520
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Official URL: http://doi.org/10.1039/B925468D
Related URL: http://dx.doi.org/10.1039/B925468D
Abstract
The flexible three-component reaction of lithiated alkoxyallenes with nitriles and carboxylic acids provided a series of highly functionalised β-alkoxy-β-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.
Item Type: | Article |
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Source: | Copyright of this article belongs to Royal Society of Chemistry. |
ID Code: | 126549 |
Deposited On: | 17 Oct 2022 05:50 |
Last Modified: | 17 Oct 2022 05:50 |
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