Journal of Organic Chemistry
Journal of Organic Chemistry
5 years ago

Copper-Catalyzed Oxidative Coupling of β-Keto Esters with N-Methylamides for the Synthesis of Symmetrical 2,3,5,6-Tetrasubstituted Pyridines

Copper-Catalyzed Oxidative Coupling of β-Keto Esters with N-Methylamides for the Synthesis of Symmetrical 2,3,5,6-Tetrasubstituted Pyridines
Zheng Li, Hongyi Li, Miaomiao Shi, Yizhe Yan, Yanqi Liu, Bin Niu
A copper-catalyzed oxidative formal [2+2+1+1] cycloaddition for the synthesis of symmetrical tetrasubstituted pyridines was first demonstrated. The reaction is involved in a domino cross-dehydrogenative coupling (CDC) of β-keto esters and N-methylamides, the C–N bond cleavage, the Michael addition, and a condensation and oxidative aromatization process. Multiple C–C and C–N bonds were constructed in one pot via the C–H and C–N cleavage of N-methylamides, which were employed as the carbon source of pyridines. The preliminary mechanistic studies revealed that the C(sp3)–H bond cleavage of N-methylamides was the rate-determining step.

Publisher URL: http://dx.doi.org/10.1021/acs.joc.7b01516

DOI: 10.1021/acs.joc.7b01516

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