Journal of Organic Chemistry
Journal of Organic Chemistry
4 years ago

Synthesis of Functionalized Pyridines via Cu(II)-Catalyzed One-Pot Cascade Reactions of Inactivated Saturated Ketones with Electron-Deficient Enamines

Synthesis of Functionalized Pyridines via Cu(II)-Catalyzed One-Pot Cascade Reactions of Inactivated Saturated Ketones with Electron-Deficient Enamines
Ze Wang, Xinying Zhang, Guang Chen, Xuesen Fan
In this paper, a novel and efficient synthesis of 3-acylpyridines and pyridine-3-carboxylates through the oxidative one-pot sequential reactions of inactivated saturated ketones with electron-deficient enamines is presented. Mechanistically, the formation of the title compounds involves the in situ formation of an enone intermediate through an oxidative dehydrogenation of the saturated ketone substrate, followed by its [3+3] annulation with β-enaminone or β-enaminoester via a cascade process, including Michael addition, aldol type condensation, and oxidative aromatization.

Publisher URL: http://dx.doi.org/10.1021/acs.joc.7b01901

DOI: 10.1021/acs.joc.7b01901

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