910896-82-1Relevant academic research and scientific papers
Copper-catalyzed cycloisomerization of unactivated allene-tethered O-propargyl oximes: A domino reaction sequence toward the synthesis of hexahydropyrrolo[3,4- b]azepin-5(4 H)-ones
Nikbakht, Ali,Amiri, Kamran,Khosravi, Hormoz,Zhou, Yirong,Balalaie, Saeed,Breit, Bernhard
supporting information, p. 3343 - 3348 (2021/05/07)
A novel copper-catalyzed cycloisomerization of unactivated allene-tethered O-propargyl oximes has been developed for the synthesis of hexahydropyrrolo[3,4-b]azepin-5(4H)-ones. This one-pot domino reaction proceeds via a [2,3]-sigmatropic rearrangement, a
Gold-Catalyzed Cyclization/Intermolecular Methylene Transfer Sequence of O-Propargylic Oximes Derived from Glyoxylates
Gima, Shinya,Shiga, Keigo,Terada, Masahiro,Nakamura, Itaru
supporting information, p. 393 - 395 (2019/02/26)
We successfully extended our gold-catalyzed skeletal rearrangement reaction of O -propargylic oximes through C=N bond cleavage to include substrates having an ester group on the oxime moiety, affording the corresponding 2-isoxazolines having an alkoxycarb
Copper-catalyzed skeletal rearrangement of o -propargylic aryloximes into four-membered cyclic nitrones - Chirality transfer and mechanistic insight
Nakamura, Itaru,Kudo, Yu,Araki, Toshiharu,Zhang, Dong,Kwon, Eunsang,Terada, Masahiro
supporting information; experimental part, p. 1542 - 1550 (2012/06/18)
Copper-catalyzed skeletal rearrangement of O-propargylic aryloximes (E)-1 were carried out to afford the corresponding four-membered cyclic nitrones 2 in good to excellent yields. The optimal reactions conditions of the highly regioselective reactions inv
Thermally-induced skeletal rearrangement of (Z)-O-propargylic α,β-unsaturated aldoximes to multisubstituted pyridine oxides
Nakamura, Itaru,Zhang, Dong,Terada, Masahiro
supporting information; experimental part, 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
Regioselective transformation of O-propargylic arylaldoximes to four-membered cyclic nitrones by copper-catalyzed skeletal rearrangement
Nakamura, Itaru,Araki, Toshiharu,Zhang, Dong,Kudo, Yu,Kwon, Eunsang,Terada, Masahiro
supporting information; experimental part, p. 3616 - 3619 (2011/09/15)
(E)-O-Propargylic arylaldoximes were regioselectively converted, in the presence of copper catalysts, into their corresponding four-membered cyclic nitrones in good to excellent yields. The reactions proceeded via a tandem [2,3]-rearrangement and 4π-elect
New regiospecific catalytic approaches to 4,5-dihydroisoxazoles and 2,5-dihydroisoxazoles from o-propargylic hydroxylamines
Knight, David W.,Proctor, Anthony J.,Clough, John M.
scheme or table, p. 628 - 632 (2010/09/18)
Unprotected O-propargylic hydroxylamines undergo generally essentially quantitative cyclisations when exposed briefly to silver nitrate adsorbed onto silica gel to give 4,5-dihydroisox-azoles [2-isoxazolines], while N-protected derivatives give the corres
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.
On the viability of 5-endo-dig cyclisations of O-propargylic hydroxylamine derivatives, leading to 2,5-dihydroisoxazoles (3-isoxazolines)
Foot, Oliver F.,Knight, David W.,Low, Ai Cheng Lilian,Li, YingFa
, p. 647 - 650 (2007/10/03)
O-Propargylic hydroxylamines undergo smooth 5-endo-dig cyclisations upon exposure to 3 equiv of molecular iodine to give respectable yields of the corresponding 4-iodo-2,5-dihydroisoxazoles, which should find a number of applications as intermediates for syntheses amongst this useful class of heterocycles.
