22661-23-0Relevant academic research and scientific papers
S -Tetrazine: Robust and Green Photoorganocatalyst for Aerobic Oxidation of N,N-Disubstituted Hydroxylamines to Nitrones
Lyu, Jiyuan,Le, Tuan,Claraz, Aurélie,Allain, Clémence,Audebert, Pierre,Masson, Géraldine
supporting information, p. 177 - 181 (2021/12/06)
Efficient photocatalytic aerobic oxidative dehydrogenation reactions of N,N-disubstituted hydroxylamines to nitrones were developed with an in situ generated photocatalyst based on commercially available 3,6-dichlorotetrazine. This process affords a wide range of nitrones in high yields under mild conditions. In addition, an oxidative (3+3) cycloaddition between an oxyallyl cation precursor and a hydroxylamine was also developed.
Sc(OTf)3-catalyzed [3 + 2]-cycloaddition of nitrones with ynones
He, Chun-Ting,Han, Xiao-Li,Zhang, Yan-Xue,Du, Zhen-Ting,Si, Chang-Mei,Wei, Bang-Guo
, p. 457 - 466 (2021/01/29)
An efficient approach to access functionalized (2,3-dihydroisoxazol-4-yl) ketones has been developed by reacting nitrones 4 with ynones 7 or terminal ynones 10 in a one-pot fashion. The reaction went through a formal Sc(OTf)3-catalyzed [3 + 2]-cycloaddition process to generate a number of functionalized (2,3-dihydroisoxazol-4-yl) ketones 11aa-11aw, 11ba-11la and 12aa-12ae in moderate to good yields. This journal is
BPh3-Catalyzed [2+3] Cycloaddition of Ph3PCCO with Aldonitrones: Access to 5-Isoxazolidinones with Exocyclic Phosphonium Ylide Moieties
Brar, Amandeep,Unruh, Daniel K.,Ling, Natalie,Krempner, Clemens
, p. 6305 - 6309 (2019/08/20)
A method for the generation of 5-isoxazolidinones with exocyclic phosphonium ylide functionalities via [2+3] cycloaddition of Ph3PCCO and aldonitrones has been developed and applied in the synthesis of 4-alkylidene-5-isoxazolidinones via Wittig olefination. The reaction proceeds by BPh3 catalysis under mild conditions and with a broad substrate scope. A reaction pathway involving the activation of the aldonitrone via interactions with the Lewis acid BPh3 is proposed.
Accessing benzooxadiazepines: Via formal [4 + 3] cycloadditions of aza- o -quinone methides with nitrones
Zheng, Yong-Sheng,Tu, Liang,Gao, Li-Mei,Huang, Rong,Feng, Tao,Sun, Huan,Wang, Wen-Xuan,Li, Zheng-Hui,Liu, Ji-Kai
, p. 2639 - 2642 (2018/04/27)
An unprecedented and efficient [4 + 3] cycloaddition of N-(ortho-chloromethyl)aryl amides with nitrones has been developed. This approach provides easy access to a series of seven-membered benzooxadiazepine derivatives in good to excellent yields (up to 99% yield) under mild reaction conditions.
Synthesis of 4-Isoxazolines through Gold(I)-Catalyzed Cyclization of Propargylic N-Hydroxylamines
Chandrasekhar,Ahn, Sewon,Ryu, Jae-Sang
, p. 6740 - 6749 (2016/08/16)
New catalytic methods for the synthesis of 4-isoxazolines have been developed via catalytic intramolecular cyclizations of propargylic N-hydroxylamines. The reactions proceed rapidly in less than 1 h at room temperature in the presence of 5 mol % (PPh3)AuCl/5 mol % AgOTf or 5 mol % (PPh3)AuNTf2. This process features an efficient route to 4-isoxazolines with high yields, short reaction times, and mild reaction conditions.
Kinetics studies of rapid strain-promoted [3+2] cycloadditions of nitrones with bicyclo[6.1.0]nonyne
Mackenzie, Douglas A.,Pezacki, John Paul
, p. 337 - 340 (2014/05/06)
Strain-promoted alkyne-nitrone cycloaddition (SPANC) reactions represent a bioorthogonal labeling strategy that is both very rapid and at the same time efficient and selective. Nitrones provide increased reaction rates as well as greater susceptibility to
Nitrones as dipoles for rapid strain-promoted 1,3-dipolar cycloadditions with cyclooctynes
McKay, Craig S.,Moran, Joseph,Pezacki, John Paul
body text, p. 931 - 933 (2010/06/12)
Strain-promoted cycloadditions of nitrones with cyclooctynes (k2 = 1.5 M-1 s-1 at 25 °C) are up to 25 times more rapid than comparable reactions of azides. The Royal Society of Chemistry 2010.
Nafion supported molybdenum oxychloride: Recyclable catalyst for one-pot synthesis of nitrones via direct condensation/oxidation of primary amines and aldehydes using UHP as oxidant
Singh, Bhawan,Jain, Suman L.,Khatri, Praveen K.,Sain, Bir
scheme or table, p. 1941 - 1944 (2010/06/15)
Immobilization of molybdenum(vi) oxychloride to the surface of perfluorinated ion-exchange polymer "Nafion"via an ion exchange method was carried out for the first time. The prepared Nafion immobilized molybdenum(vi) oxychloride catalyst was used for the direct synthesis of nitrones via one-pot condensation/oxidation of primary amines with aldehydes using solid urea-hydrogen peroxide (UHP) as oxidant under very mild reaction conditions. The developed polymer immobilized catalyst showed better activity than its analogous homogeneous catalyst with the added benefits of facile recovery and recyclability of the catalyst without leaching and loss in catalytic activity.
The cycloaddition of nitrones with homochiral cyclopropanes
Sapeta, Katarina,Kerr, Michael A.
, p. 8597 - 8599 (2008/03/12)
(Chemical Equation Presented) The cycloaddition of nitrones and enantiomerically pure cyclopropane-1,1-dicarboxylates is examined. Transfer of optical activity to the adduct is dictated by thermal reaction conditions and nature of cyclopropane substitutio
Catalytic oxidation of imines based on methyltrioxorhenium/urea hydrogen peroxide: A mild and easy chemo- and regioselective entry to nitrones
Soldaini, Gianluca,Cardona, Francesca,Goti, Andrea
, p. 473 - 476 (2007/10/03)
The first successful catalytic oxidation procedure for the chemoselective conversion of imines to nitrones is reported. The reaction is general, high yielding, and user and environmentally friendly, and furnishes a solution to the yet unanswered issue of
