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

Guang Chen, Ze Wang, Xinying Zhang* and Xuesen Fan*

*School of Chemistry and Chemical Engineering, Henan Normal University, Xinxiang, Henan 453007, China, Email: xinyingzhanghtu.cn, xuesen.fanhtu.cn,

G. Chen, Z. Wang, X. Zhang, X. Fan, J. Org. Chem., 2017, 82, 11230-11237.

DOI: 10.1021/acs.joc.7b01901

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Abstract

Oxidative one-pot sequential reactions of inactivated saturated ketones with electron-deficient enamines enable an efficient synthesis of 3-acylpyridines and pyridine-3-carboxylates. The reaction involve oxidative dehydrogenation of the saturated ketone substrate, followed by [3+3] annulation with β-enaminone or β-enaminoester via a cascade process, including Michael addition, aldol type condensation, and oxidative aromatization.

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proposed mechanism

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Access to 4,6-Diarylpicolinates via a Domino Reaction of Cyclic Sulfamidate Imines with Morita-Baylis-Hillman Acetates of Nitroolefins/Nitrodienes

D. Majee, S. Biswas, S. M. Mobin, S. Samanta, J. Org. Chem., 2016, 81, 4378-4385.

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Key Words

pyridines, TEMPO, oxygen

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ID: J42-Y2017