1228682-57-2Relevant academic research and scientific papers
Thermally-induced skeletal rearrangement of (Z)-O-propargylic α,β-unsaturated aldoximes to multisubstituted pyridine oxides
Nakamura, Itaru,Zhang, Dong,Terada, Masahiro
, p. 6470 - 6472 (2011/12/16)
(Z)-Propargylic oxime ethers derived from α,β-unsaturated aldehydes were converted to the corresponding 2,3,6-trisubstituted pyridine oxides in moderate to acceptable yields with high regioselectivity. The reaction proceeds via a tandem thermal [2,3] rear
Copper-catalyzed tandem [2,3]-Rearrangement and 6π-3-Azatriene electrocyclization in (E) -O -Propargylic α,β-Unsaturated oximes
Nakamura, Itaru,Zhang, Dong,Terada, Masahiro
supporting information; experimental part, p. 7884 - 7886 (2010/07/16)
Cu-catalyzed cyclizations of (E)-O-propargylic oximes of α,β-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 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 6-3-azatriene electrocyclization.
