Flexible strategy for differentially 3,5-disubstituted 4-oxypyridin-2(1H)-ones based on site-selective Pd-catalyzed cross-coupling reactions.
3,5-Dihalogeno-4-methoxy-N-methylpyridin-2(1H)-ones have been shown to undergo single Suzuki coupling reactions in a site-selective fashion. Monoarylations occur at the C-5 position preferentially, thus leaving the remaining C-3 halide free for further functionalization, to finally access differentially 3,5-disubstituted 2-pyridones. This two-step strategy has been applied to the elaboration of the 3-acyl-5-aryl-4-oxy-2-pyridone subunit that is prevalent in numerous bioactive natural products. [reaction: see text].
Conreaux
David
D
Laboratoire de Synthèse Organométallique et Molécules Bioactives, CNRS UMR 5181, Université Claude Bernard-Lyon 1, ESCPE Lyon 43, Boulevard du 11 Novembre 1918, 69622 Villeurbanne, France.
Bossharth
Emmanuel
E
Monteiro
Nuno
N
Desbordes
Philippe
P
Vors
Jean-Pierre
JP
Balme
Geneviève
G
D000085:Acetates / Q000737:chemistry*; D002384:Catalysis; D015394:Molecular Structure; D010165:Palladium / Q000737:chemistry*; D011728:Pyridones / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
D000085:Acetates; D011728:Pyridones; D010165:Palladium