22661-25-2Relevant articles and documents
A green synthesis of nitrones in glycerol
Shariatipour, Monire,Jadidinejad, Masoumeh,Heydari, Akbar
, (2019/11/11)
Abstract: An eco-friendly and efficient synthesis of nitrones is presented by condensation of an equimolar amount of aldehydes and N-substituted hydroxylamine hydrochlorides in glycerol as a recyclable solvent-catalyst. This novel protocol provides rapid and mild access to a series of nitrone derivatives in good to excellent yields in the absence of catalyst and base. Graphic abstract: SYNOPSIS In this study, a base-free protocol by using glycerol as the solvent-catalyst was applied for an eco-friendly synthesis of nitrones from the condensation of aldehydes and N-substituted hydroxylaminehydrochlorides.[Figure not available: see fulltext.].
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.
Highly Stereoselective Synthesis of New Aziridines via Baldwin Rearrangement and Their Potential Biological Activities
Chakraborty, Bhaskar,Chhetri, Manjit Singh,Chhetri, Esmita
, p. 110 - 120 (2017/02/03)
An atom-economical conversion of N-substituted isoxazoline derivatives to new N-substituted aziridines has been described using microwave irradiation through Baldwin rearrangement. N-substituted isoxazoline derivatives have been synthesized using a variet
α,β-Unsaturated Amides as Dipolarophiles: Catalytic Asymmetric exo-Selective 1,3-Dipolar Cycloaddition with Nitrones
Zhang, Ming,Kumagai, Naoya,Shibasaki, Masakatsu
supporting information, p. 12450 - 12455 (2017/09/18)
1,3-Dipolar cycloaddition is a commonly exploited method to access 5-membered chemical entities with a variety of peripheral functionalities and their stereochemical arrangements. Nitrones are isolable 1,3-dipoles that exhibit sufficient reactivity toward electron-deficient olefins in the presence of Lewis acids to deliver highly substituted isoxazolidines. Herein we document that α,β-unsaturated amides, generally regarded as barely reactive in a 1,3-dipolar reaction manifold, were effectively activated using the designed 7-azaindoline auxiliary in an In(OTf)3/bishydroxamic acid catalytic system. The broad substrate scope and clean removal of the 7-azaindoline auxiliary from the product highlight the synthetic utility of the present catalysis.
Efficient combination of task-specific ionic liquid and microwave dielectric heating applied to synthesis of a large variety of nitrones
Valizadeh, Hassan
experimental part, p. 78 - 83 (2011/04/16)
Under mild microwave irradiation conditions and without any additional organic solvents, a large variety of nitrones were prepared in a weak Lewis base phosphinite task-specific ionic liquid (TSILOPPh2) in excellent yields. This catalytic TSIL was also re
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.
Solvent-free synthesis of nitrones in a ball-mill
Colacino, Evelina,Nun, Pierrick,Colacino, Francesco Maria,Martinez, Jean,Lamaty, Frédéric
, p. 5569 - 5576 (2008/09/21)
Various C-aryl and C-alkyl-nitrones were synthesized within 0.5-2 h via condensation of an equimolar amount of aldehydes and N-substituted-hydroxylamines under solvent-free conditions in?a ball-mill apparatus. Reactions can be performed without the need of excluding air and moisture and yields the expected products with no need for further purification. The study has been complemented by Differential Scanning Calorimetry (DSC) and solid-state 13C MAS nuclear magnetic resonance experiments. We have also studied the temperature profile during the reaction. A comparative study with the corresponding solvent-free microwave activated reaction showed the superiority of the ball-milling method; 31 examples are described, including the synthesis of the anti-aging agent C-phenyl-N-tert-butyl nitrone (PBN) and one of its analogues C-2-pyridyl-N-tert-butylnitrone (2-PyBN).
1,3-Dipolar cycloadditions of N-benzyl furfuryl nitrones with electron-rich alkenes
Merino, Pedro,Anoro, Sonia,Merchan, Francisco L.,Tejero, Tomas
, p. 132 - 152 (2007/10/03)
The 1,3-dipolar cycloaddition reaction of N-benzyl-C-(2-furyl)nitrones with electron-rich alkenes gives preferentially trans-substituted 3,5-disubstituted isoxazolidines (endo approach). These experimental results are in good qualitative agreement with th
