期刊
JOURNAL OF ORGANIC CHEMISTRY
卷 82, 期 16, 页码 8628-8633出版社
AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.7b01516
关键词
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资金
- National Natural Science Foundation of China [21502177]
- Science and Technology Research Key Project of the Department of Education of Henan Province [15A150005]
- Doctoral Research Foundation of Zhengzhou University of Light Industry [2014BSJJ032]
- Youth Backbone Teachers Training Object of Zhengzhou University of Light Industry
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 beta-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(sp(3))-H bond cleavage of N-methylamides was the rate-determining step.
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