期刊
JOURNAL OF ORGANIC CHEMISTRY
卷 86, 期 11, 页码 7832-7841出版社
AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.1c00717
关键词
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资金
- National Natural Science Foundation of China [21871218, 22050410277]
- Natural Science Basic Research Plan in Shaanxi Province of China [2020JM-003]
- Fundamental Research Funds for the Central Universities
- Key Laboratory Construction Program of Xi'an Municipal Bureau of Science and Technology [201805056ZD7CG40]
In this reaction, cyclic amidines act as C,N-bisnucleophiles for cyclization, while olefins play a dual role as reactants and oxidants.
Herein we describe a catalyst-free regioselective [3 + 3] annulation/oxidation reaction of cyclic amidines such as DBU (1,8-diazabicyclo(5.4.0)undec-7-ene) and DBN (1,5-diazabicyclo(4.3.0)non-5-ene) with activated olefins, i.e., 2-arylidenemalononitriles and 2-cyano-3-aryl acrylates, to afford tricyclic 2-pyridones and pyridin-2(1H)-imines, respectively. The mechanism has been proposed based on DFT calculations. In the reaction, the cyclic amidines serve as C,N-bisnucleophiles for the cyclization, while the olefins play a dual role by acting as both reactants and oxidants.
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