72552-76-2Relevant academic research and scientific papers
Reductive approach to nitrones from N-Siloxyamides and N-Hydroxyamides
Katahara, Seiya,Kobayashi, Shoichiro,Fujita, Kanami,Matsumoto, Tsutomu,Sato, Takaaki,Chida, Noritaka
, p. 893 - 904 (2017/08/07)
This article describes the full details of our reductive approach to nitrones from amides. Reduction of N-siloxyamides with the Schwartz reagent [Cp2ZrHCl], followed by addition of an acid provided functionalized nitrones. The developed conditi
Diruthenium Diacetate Catalysed Aerobic Oxidation of Hydroxylamines and Improved Chemoselectivity by Immobilisation to Lysozyme
Lupi, Flavia,Marzo, Tiziano,D'Adamio, Giampiero,Cretella, Sara,Cardona, Francesca,Messori, Luigi,Goti, Andrea
, p. 4225 - 4230 (2017/12/02)
A new green method for the preparation of nitrones through the aerobic oxidation of the corresponding N,N-disubstituted hydroxylamines has been developed upon exploring the catalytic activity of a diruthenium catalyst, that is, [Ru2(OAc)4Cl]), in aqueous or alcoholic solution under mild reaction conditions (0.1 to 1 mol % catalyst, air, 50 °C) and reasonable reaction times. Notably, the catalytic activity of the dimetallic centre is retained after its binding to the small protein lysozyme. Interestingly, this new artificial metalloenzyme conferred complete chemoselectivity to the oxidation of cyclic hydroxylamines, in contrast to the diruthenium catalyst.
An Iridium-Catalyzed Reductive Approach to Nitrones from N-Hydroxyamides
Katahara, Seiya,Kobayashi, Shoichiro,Fujita, Kanami,Matsumoto, Tsutomu,Sato, Takaaki,Chida, Noritaka
, p. 5246 - 5249 (2016/05/19)
An Ir-catalyzed reductive formation of functionalized nitrones from N-hydroxyamides was reported. The reaction took place through two types of iridium-catalyzed reactions including dehydrosilylation and hydrosilylation. The method showed high chemoselectivity in the presence of sensitive functional groups, such as methyl esters, and was successfully applied to the synthesis of cyclic and macrocyclic nitrones, which are known to be challenging compounds to access by conventional methods. 1H NMR studies strongly supported generation of an N-siloxyamide and an N,O-acetal as the actual intermediates.
Gold Supported on Silica Catalyzes the Aerobic Oxidation of N,N-Disubstituted Hydroxylamines to Nitrones
D'Adamio, Giampiero,Parmeggiani, Camilla,Goti, Andrea,Cardona, Francesca
supporting information, p. 6541 - 6546 (2015/10/19)
A new method for the preparation of nitrones through the aerobic oxidation of the corresponding N,N-disubstituted hydroxylamines has been developed by exploring a new catalytic reactivity of gold supported on silica. The oxidation occurs under very mild c
Oxidation of N,N-Disubstituted Hydroxylamines to Nitrones with Hypervalent Iodine Reagents
Matassini, Camilla,Parmeggiani, Camilla,Cardona, Francesca,Goti, Andrea
supporting information, p. 4082 - 4085 (2015/09/01)
Hypervalent iodine compounds are viable reagents for the oxidation of N,N-disubstituted hydroxylamines to the corresponding nitrones, with IBX performing best. The procedure is very simple and user-friendly and affords the target compounds with high effic
Synthesis and X-ray Analysis of Dihydro-1,2,4,5-trioxazine. Evidence of a Steowise Mechanism for the Cycloaddition of Carbonyl Oxides with Nitrones
Mori, Mitsuyuki,Sugiyama, Tomohito,Nojima, Masatomo,Kusabayashi, Shigekazu,McCullough, Kevin J.
, p. 2285 - 2294 (2007/10/02)
Carbonyl oxides, derived by ozonolysis of vinyl ethers, readily undergo cycloaddition reactions with nitrones affording dihydro-1,2,4,5-trioxazines in fair to excellent yield.The structures of dihydro-3,5,6-triphenyl-1,2,4,5-trioxazine (5f) and dihydro-3-cyclohexyl-5-methyl-6,6-diphenyl-1,2,4,5-trioxazine (5t) were unambiguously determined by X-ray analysis.Ozonolysis of 1-cyclohexyl-2-methoxyethene in the presence of either (E)- or (Z)-α-(4-methylphenyl)-α-phenyl-N-methylnitrone gave a 1:1 mixture of two stereoisomeric cycloadducts.This result, in conjunction with the structure of the relevant 5t, suggests that the cycloaddition proceeds by a stepwise mechanism.
