Categories: Synthesis of N-Heterocycles >
Synthesis of 2-pyridones
Recent Literature
The chemo- and regioselective reaction of the Blaise intermediate, generated in
situ from Reformatsky reagent and nitrile, with propiolates affords 2-pyridone
derivatives in good to excellent yields.
Y. S. Chun, K. Y. Ryu, Y. O. Ko, J. Y. Hong, J. Hong, H. Shin, S.-g. Lee, J. Org. Chem., 2009,
74, 7556-7558.
Formation of N-alkenyl alkynylamides by N-acylation of imines with
alkynoyl chlorides and the subsequent cationic Au(I)/PPh3-catalyzed
cycloisomerization allows a convergent and rapid assembly of substituted
2-pyridones.
H. Imase, K. Noguchi, M. Hirano, K. Tanaka, Org. Lett.,
2008,
10, 3563-3566.
CuI-catalyzed coupling reactions of tetrabutylammonium pyridin-2-olates with
aryl iodides allow an efficient synthesis of N-aryl pyridine-2-ones. This
coupling reaction is mild, high-yielding, remarkably chemoselective (N- vs.
O-arylation), and tolerates labile functional groups.
H. Zhang, B.-C. Chen, B. Wang, S. T. Chao, R. Zhao, N. Lim, B. Balasubramanian, Synthesis, 2008,
1523-1524.
A tandem condensation of propiolamide and cyclic β-keto methyl esters in water,
followed by acid- or base-promoted intramolecular ring closure and
decarboxylation enables an efficient synthesis of a 5,6-fused 2-pyridone
ring system.
A. B. Smith, III, O. Atasoylu, D. C. Beshore, Synlett, 2009,
2643-2646.
