Organic Chemistry Portal



Synthesis of 6-Substituted-4-Hydroxy-2-pyridinones via Intramolecular Ketene Trapping of Functionalized Enamine-Dioxinones

Bhavesh H. Patel, Andrew M. Mason and Anthony G. M. Barrett*

*Department of Chemistry, Imperial College, London SW7 2AZ, U.K., and GlaxoSmithKline R&D, Gunnels Wood Road, Stevenage, Herts SG1 2NY, U.K., Email:

B. H. Patel, A. M. Mason, A. G. M. Barrett, Org. Lett., 2011, 13, 5156-5159.

DOI: 10.1021/ol202028t


Enamine formation of substituted keto-dioxinones followed by thermolysis and cyclization-aromatization enables the synthesis of various 6-substituted-4-hydroxy-2-pyridinones in good yields. The functionalized keto-dioxinones were constructed via a diethylzinc mediated crossed Claisen condensation reaction.

see article for more examples

Key Words


ID: J54-Y2011-2860