85225-53-2

Upstream product

• 3378-72-1 N-tert-butylbenzylamine 
• 6852-58-0 (E)-N-benzylidene-2-methylpropan-2-amine 
• 3585-81-7 2-tert-butyl-3-phenyloxaziridine 
• 57497-39-9 N-tertbutylhydroxylamine hydrochloride 
• 100-52-7 benzaldehyde 
• 917-95-3 t-butylnitrite 
• 66045-11-2 aci-nitromethyl-benzene; potassium-compound 
• 594-70-7 2-Methyl-2-nitropropane 
• 118891-49-9 C₇H₁₆NO₂⁽¹⁺⁾*CF₃O₃S^(1-) 
• 118891-54-6 methyl N-(1,1-dimethylethyl)benzenecarboximidate N-oxide 
• 16649-50-6 N-tert-Butylhydroxylamine 

Downstream Products

• 6852-58-0 N-benzylidene tert-butylamine 
• 34234-86-1 α-Methoxybenzyl-tert-butyl-nitroxyl-Radikal 
• 34280-33-6 methanol adduct of α-phenyl-N-t-butylnitrone 
• 72023-85-9 C₁₄H₂₂NO₂ 
• 102564-44-3 N-tert-Butyl-N-(1-phenylethyl)hydroxylamine 
• 21894-26-8 C₁₂H₁₅F₃NO 
• 134390-29-7 2-tert-butyl-4-carbomethoxy-5-<<(2,4-dinitrophenyl)sulfenyloxy>methyl>-3-phenyl-Δ⁴-isoxazoline 
• 137578-85-9 2-tert-butyl-4-methylcarboxy-3,5-diphenyl-4-isoxazoline 
• 3585-81-7 2-tert-butyl-3-phenyloxaziridine 
• 5894-65-5 N-t-butylbenzamide 
• 35822-90-3 benzoyl-tert-butylnitroxyl radical 
• 55482-05-8 α-Hydroxybenzyl-tert-butyl-nitroxyl 
• 24293-08-1 N-tert-butyl-N-benzylnitroxyl 
• 16649-50-6 N-tert-Butylhydroxylamine 

Relevant academic research and scientific papers

Synthesis of nitrones by methyltrioxorhenium catalyzed direct oxidation of secondary amines

Oxidation of secondary amines catalyzed by methyltrioxorhenium (MTO) with H2O2 or urea-hydrogen peroxide complex (UHP) at room temperature gives the corresponding nitrones in good yields.

Aliphatic nitro compounds chemistry: oximes–nitrones tunable production through directed tandem synthesis

Abstract: Reduction of aliphatic nitro compounds in the presence of aldehydes and dialdehydes for tunable directed synthesis of oximes, nitrones, nitrone–oximes, and dinitrones was reported. The slow and nonselective reduction of aliphatic nitro compounds was directed by condensation of in situ prepared alkylhydroxylamines with aromatic aldehydes. Mononitrones and dinitrones were synthesized at reflux and at 55?°C conditions, respectively, in tetrahydrofuran using SnCl2?2H2O and Na2CO3. It was found that the presence of a catalytic amount of carboxylic acid such as 3-phenylpropanoic acid increases the yield of dinitrones versus nitrone–oxime and dioxime when dialdehydes were used as aldehyde source. Graphical abstract: [Figure not available: see fulltext.].

An asymmetric pericyclic cascade approach to 3-alkyl-3-aryloxindoles: Generality, applications and mechanistic investigations

The reaction of L-serine derived N-arylnitrones with alkylarylketenes generates asymmetric 3-alkyl-3-aryloxindoles in good to excellent yields (up to 93%) and excellent enantioselectivity (up to 98% ee) via a pericyclic cascade process. The optimization, scope and applications of this transformation are reported, alongside further synthetic and computational investigations. The preparation of the enantiomer of a Roche anti-cancer agent (RO4999200) 1 (96% ee) in three steps demonstrates the potential utility of this methodology.

Stereoselective synthesis of fluoroalkenoates and fluorinated isoxazolidinones: N-substituents governing the dual reactivity of nitrones

α-Fluoroalkenoates and 4-fluoro-5-isoxazolidinones are of vast interest due to their potential biological applications. We now demonstrate the syntheses of (E)-α-fluoroalkenoates and 4-fluoro-5-isoxazolidinones by the reactions between nitrones and α-fluoro-α-bromoacetate. By altering N-substituents in nitrones, (E)-α-fluoroalkenoates and 4-fluoro-5-isoxazolidinones can be achieved, respectively, with high chemo- and stereoselectivities. Experimental and computational studies have been conducted to elucidate the reaction mechanisms. Linear free energy relationship studies further revealed that the N-substituent effects are primarily of electronic origin. Copyright

Microwave-assisted synthesis of hydroxyphenyl nitrones with protective action against oxidative stress

Oxidative stress plays an important role in neuronal death in neurodegenerative disorders such as Parkinson's disease (PD). Hydroxyphenyl nitrones, derivatives of the nitrone spin trap alpha-phenyl-N-tert-butylnitrone (PBN), were synthesized and their antioxidant, anti-inflammatory and neuroprotective activity in neural cells evaluated. These hydroxyphenyl nitrones 5-7 were synthesized by reaction of the corresponding hydroxybenzaldehyde with N-tert-butyl hydroxylamine under microwave irradiation. They showed good peroxyl free radical scavenger capacities, analyzed by oxygen radical absorbance capacity (ORAC). Also inhibited peroxynitrite-mediated tyrosine nitration of alpha-synuclein in vitro and protected human neuroblastoma (SH-SY5Y) cells against SIN-1 and 6-OHDA toxicity when micromolar concentrations were used. Besides, the hydroxyphenyl nitrones evaluated showed anti-inflammatory activity modulating nitrite production in primary neural cell cultures of astrocytes and microglia treated with lipopolysaccharide (LPS), a potent inflammatory agent. These experimental data suggest a potential therapeutic use of these hydroxyphenyl nitrones against oxygen and nitrogen reactive species involved in neurodegenerative pathology.

Synthesis, structure, theoretical and experimental in vitro antioxidant/pharmacological properties of α-aryl, N-alkyl nitrones, as potential agents for the treatment of cerebral ischemia

The synthesis, structure, theoretical and experimental in vitro antioxidant properties using the DPPH, ORAC, and benzoic acid, as well as preliminary in vitro pharmacological activities of (Z)-α-aryl and heteroaryl N-alkyl-nitrones 6-15, 18, 19, 21, and 23, is reported. In the in vitro antioxidant activity, for the DPPH radical test, only nitrones bearing free phenol groups gave the best RSA (%) values, nitrones 13 and 14 showing the highest values in this assay. In the ORAC analysis, the most potent radical scavenger was nitrone indole 21, followed by the N-benzyl benzene-type nitrones 10 and 15. Interestingly enough, the archetypal nitrone 7 (PBN) gave a low RSA value (1.4%) in the DPPH test, or was inactive in the ORAC assay. Concerning the ability to scavenge the hydroxyl radical, all the nitrones studied proved active in this experiment, showing high values in the 94-97% range, the most potent being nitrone 14. The theoretical calculations for the prediction of the antioxidant power, and the potential of ionization confirm that nitrones 9 and 10 are among the best compounds in electron transfer processes, a result that is also in good agreement with the experimental values in the DPPH assay. The calculated energy values for the reaction of ROS (hydroxyl, peroxyl) with the nitrones predict that the most favourable adduct-spin will take place between nitrones 9, 10, and 21, a fact that would be in agreement with their experimentally observed scavenger ability. The in vitro pharmacological analysis showed that the neuroprotective profile of the target molecules was in general low, with values ranging from 0% to 18.7%, in human neuroblastoma cells stressed with a mixture of rotenone/oligomycin-A, being nitrones 18, and 6-8 the most potent, as they show values in the range 24-18.4%.

Solvent-free synthesis of nitrones in a ball-mill

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).

Exploiting microwave-assisted neat procedures: synthesis of N-aryl and N-alkylnitrones and their cycloaddition en route for isoxazolidines

Microwave irradiation allows increasing the speed of several reactions and also offers the possibility of eliminating poisoning organic solvents. In this work we report the microwave-assisted neat synthesis of α-phenyl-tert-butylnitrone (PBN) and other alkyl and aryl nitrones and also the rapid synthesis of isoxazolidines resulting from 1,3-dipolar cycloaddition of nitrones to ethyl trans-crotonate.

Synthesis of new 3,5-diarylisoxazolidines by cycloaddition of oxaziridines and alkenes

This article reports a novel process of cycloaddition of C-aryloxaziridines with a variety of alkenes to afford stable, five-membered heterocycles 13-24. The steric hindrance of the tert-butyl group on the nitrogen atom of the oxaziridine is responsible for the high stereoselectivity of the cycloaddition reaction.

Ti(IV)/trialkanolamine catalytic polymeric membranes: Preparation, characterization, and use in oxygen transfer reactions

New heterogeneous oxidation catalysts have been obtained by entrapping Ti(IV)/trialkanolamine complexes within polymeric membranes. The catalytic membranes were prepared by a nonsolvent-induced phase-inversion technique. Three polymers, polyvinylidene fluoride (PVDF), a modified polyetherketone (PEEK-WC), and polyacrylonitrile (PAN), with different functional groups and chemical-physical properties, were used to tune the reactivity of the catalytic polymeric membranes in the stereoselective oxidation to sulfoxide and chemoselective oxidation of secondary amines to nitrones by alkyl hidroperoxides. The chemical-physical analysis of the new catalytic membranes was carried out by SEM, EDX, IR, CAM, and XPS techniques. In particular, the XPS spectra showed a very interesting orientation effect of PVDF membranes on the entrapped Ti(IV)/trialkanolamine complex. PVDF-based catalytic membranes gave the best results, affording products in shorter reaction times, higher yields, and better selectivity compared with the corresponding homogeneous systems. The membranes can be recycled up to five runs with no loss of activity.