期刊
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
卷 132, 期 23, 页码 7884-+出版社
AMER CHEMICAL SOC
DOI: 10.1021/ja102436z
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资金
- Japan Society for Promotion in Science (JSPS)
Cu-catalyzed cyclizations of (E)-O-propargylic oximes of alpha,B-unsaturated aldehydes were successfully carried out to afford the corresponding pyridine oxides in good to high yields. As an example, (E)-acrylaldehyde O-1,3-diphenylprop-2-ynyl oxime (1b) was reacted for 5 h in the presence of CuBr(PPh3)(3) (10 mol %) and PPh3 (10 mol %) in DMSO at 120 degrees C to afford 3-benzyl-2-phenylpyridine-N-oxide (2b) in 84% yield. In this case, the reaction proceeded via Cu-catalyzed propargyl oxime-allenyl nitrone rearrangement followed by 6 pi-3-azatriene electrocyclization.
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