40117-30-4

Upstream product

• 86402-00-8 (E)-N-tert-butyl-1-(4-chlorophenyl)methanimine 
• 57497-39-9 N-tertbutylhydroxylamine hydrochloride 
• 104-88-1 4-chlorobenzaldehyde 
• 16649-50-6 N-tert-Butylhydroxylamine 
• 594-70-7 2-Methyl-2-nitropropane 
• 943-72-6 (p-chlorobenzylidene)(tert-butyl)amine 
• 23898-60-4 2-tert-butyl-3-(p-chlorophenyl)oxaziridine 
• 46234-01-9 N-(4′-chlorobenzyl)-2-methylpropan-2-amine 

Downstream Products

• 135485-62-0 C₁₈H₁₉ClNO₃ 
• 642481-98-9 (+)-2-tert-butyl-4,4-dimethyl-3-p-chlorophenylisoxazolidin-5-one 
• 642481-76-3 2-tert-butyl-4,4-dimethyl-3-p-chlorophenylisoxazolidin-5-one 

Relevant academic research and scientific papers

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.].

Dual Role of Pyrrolidine and Cooperative Pyrrolidine/Pyrrolidinium Effect in Nitrone Formation

The formation of nitrones by direct condensation between equimolecular amounts of N-substituted hydroxylamine hydrochlorides and aromatic or aliphatic aldehydes is efficiently promoted by pyrrolidine in a matter of minutes under very mild conditions in almost quantitative yields after a simple filtration through a short pad of silica gel. According to theoretical, spectroscopic, and experimental studies, this success is due to the ability of pyrrolidine to liberate the hydrochloride of the hydroxylamine and catalyze the reaction via iminium activation ion. Moreover, a cooperative pyrrolidine/pyrrolidinium chloride effect facilitates several steps of the catalytic cycle through proton transfer without hampering the nucleophilicity of the hydroxylamine by protonation.

Iridium-Catalyzed Direct C-H Sulfamidation of Aryl Nitrones with Sulfonyl Azides at Room Temperature

Ir(III)-catalyzed direct C-H sulfamidation of aryl nitrones has been developed to synthesize various sulfamidated nitrones in moderate to excellent yields with excellent regioselectivity and broad functional group tolerance. This transformation could proceed smoothly at room temperature with low catalyst loading in the absence of external oxidants, acids, or bases. Molecular nitrogen was released as the sole byproduct, thus providing an environmentally benign sulfamidation process. And this protocol could efficiently apply to synthesize the substituted benzisoxazoline via one-step transformation from the product.

Activation of C-H bonds in nitrones leads to iridium hydrides with antitumor activity

We report the design and synthesis of a series of new cyclometalated iridium hydrides derived from the C-H bond activation of aromatic nitrones and the biological evaluation of these iridium hydrides as antitumor agents. The nitrone ligands are based on the structure of a popular antioxidant, α-phenyl-N-tert-butylnitrone (PBN). Compared to cisplatin, the iridium hydrides exhibit excellent antitumor activity on HepG2 cells. The metal-coordinated compound with the most potent anticancer activity, 2f, was selected for further analysis because of its ability to induce apoptosis and interact with DNA. During in vitro studies and in vivo efficacy analysis with tumor xenograft models in Institute of Cancer Research (ICR) mice, complex 2f exhibited antitumor activity that was markedly superior to that of cisplatin. Our results suggest, for the first time, that metal hydrides could be a new type of metal-based antitumor agent.

N-tert-Butyl and N-methyl nitrones derived from aromatic aldehydes inhibit macromolecular permeability increase induced by ischemia/reperfusion in hamsters

N-Alquil nitrones 1c and 3-6 were prepared from aromatic aldehydes and N-tert-butylhydroxylamine or N-methylhydroxylamine in good yields and soft conditions. Their protective effect against microvascular damages caused by ischemia/reperfusion in 'hamster

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.

A novel route to substituted 4-methylene-4,5-dihydroisoxazoles mediated by hafnium(IV) chloride

Heating alkyl vinyl ketones and N-tert-butylarylmethylide-neamine N-oxides in the presence of HfCl4 results in the formation of 4-methylene-4,5-dihydroisoxazoles in good yield.

Chromium and Tungsten Pentacarbonyl Groups as Reactivity and Selectivity Auxiliaries in Cycloaddition of Alkynyl Fischer Carbene Complexes with N-Alkyl Nitrones

Alkynyl Fischer carbene complexes were found to undergo chemoselective, regioselective, and rate-enhanced 1,3-dipolar cycloaddition with nitrones to give 2,3-dihydroisoxazole carbene complexes in excellent yields.These alkynyl complexes can serve as synth

Synthesis and Characterization of Phenyl-Substituted C-Phenyl-N-tert-butylnitrones and Some of Their Radical Adducts

Synthesis of C-phenyl-N-tert-butylnitrone (PBN) and several of its analogues with substituents in the 2-, 3-, or 4-position on the phenyl ring is described.While a one-pot reduction/condensation method proved suitable for the most compounds, it was necessary to prepare some examples by direct condensation or through oxidation of the appropriate imine.The 1H NMR data for the 3-X- and 4-X-PBN's can be correlated with the Hammett equation.For the 3-X series Δδ for the α-proton correlates best with ?+ and has a correlation coefficient of 0.90.For the 4-X series a dual substituent parameter equation using ?R0 gives the best correlation with r = 0.99.The hyperfine splitting constants (hfsc's) of HO and HOO adducts of serveral substituted PBN's are also included and their correlation with the Hammett equation is discussed.

Imines and Derivatives. Part 24. Nitrone Synthesis by Imine Oxidation using either a Peroxyacid or Dimethyldioxirane

The oxidation of N-alkyl imines by m-chloroperoxybenzoic acid to yield nitrones was facilitated by (i) the presence of C-aryl substituents, (ii) steric inhibition of attack at the imino C-atom, (iii) electron donating para-substituents on the C-aryl substituent, (iv) non-hydroxylic solvents, (v) optimal conjugation between C-aryl substituents and the imino group, and (vi) less bulky N-alkyl groups. The oxidation of N-alkyl imines by dimethyldioxirane (DMD) in dichloromethane-acetone solution yielded nitrones without evidence of oxaziridine formation.The yields of isolated nitrones were higher for C,C-diaryl imines and for imines bearing less bulky N-alkyl substituents.N-H substituted ketimines were found to yield oximes after reaction with dimethyldioxirane.