7372-59-0

Upstream product

• 420-37-1 trimethoxonium tetrafluoroborate 
• 103559-03-1 O-(trimethylsilyl)-E-benzaldoxime 
• 57777-70-5 α,α-adamantylidene-N-methyl nitrone 
• 100-52-7 benzaldehyde 
• 22737-33-3 N-Methyl-N,O-bis(trimethylsilyl)hydroxylamine 
• 103-67-3 benzyl-methyl-amine 
• 4229-44-1 N-methylhydroxyamine hydrochloride 
• 3555-72-4 N-benzyl-N-methylhydroxylamine 
• 75-52-5 nitromethane 
• 3376-23-6 N-(benzylidene)methylamine N-oxide 
• 50455-59-9 2,2',2',4',4'-pentamethyl-3-phenylspiro<(1,4,2)-oxathiazolidine-5,3'-cyclobutane>-1'-one 
• 622-29-7 N-Benzylidenemethylamine 
• 3400-12-2 2-methyl-3-phenyl-oxaziridine 
• 333-27-7 methyl trifluoromethanesulfonate 

Downstream Products

• 51289-46-4 4-ethyl-2-methyl-3-phenyl-5-(2,2,2-trifluoro-1-trifluoromethyl-ethylidene)-[1,2,4]oxadiazolidine 
• 108817-73-8 2-methyl-5-methylene-3-phenyl-4-isoxazolidinecarbonitrile 
• 106544-25-6 2-methyl-3-phenyl-5-(1-cyano-1-methylethyl)-Δ⁴-1,2,4-oxadiazoline 
• 153392-54-2 tetrahydro-2'-methyl-3'-phenylspiro(cyclopentane-1,5'-isoxazole) 
• 144433-30-7 2,5-dimethyl-3-phenyl-2,3-dihydroisoxazole 
• 144433-21-6 trans-2,5-dimethyl-3-phenyl-5-(trimethylsiloxy)isoxazolidine 
• 144433-21-6 cis-2,5-dimethyl-3-phenyl-5-(trimethylsiloxy)isoxazolidine 
• 119099-16-0 (R,S)-<α-benzyl>phosphonsaeure-diethylester 
• 146256-57-7 1-((3S,4R)-2-Methyl-3-phenyl-isoxazolidin-4-yl)-ethanone 
• 486-25-9 9-fluorenone 
• 33226-81-2 N-fluorenylidene methylamine N-oxide 
• 100-52-7 benzaldehyde 
• 76256-14-9 2'-methyl-3'-phenylfluorene-9-spiro-4'-(1',2'-thiazolidine)-5'-spiro-9-fluorene 
• 50455-50-0 2'-methyl-3'-phenyl-spiro[adamantane-2,5'-[1,4,2]oxathiazolidine] 

Relevant academic research and scientific papers

Regio- and Enantioselective (3+3) Cycloaddition of Nitrones with 2-Indolylmethanols Enabled by Cooperative Organocatalysis

The regio- and enantioselective (3+3) cycloaddition of nitrones with 2-indolylmethanols was accomplished by the cooperative catalysis of hexafluoroisopropanol (HFIP) and chiral phosphoric acid (CPA). Using this approach, a series of indole-fused six-membered heterocycles were synthesized in high yields (up to 98 %), with excellent enantioselectivities (up to 96 % ee) and exclusive regiospecificity. This approach enabled not only the first organocatalytic asymmetric (3+3) cycloaddition of nitrones but also the first C3-nucleophilic asymmetric (3+3) cycloaddition of 2-indolylmethanols. More importantly, theoretical calculations elucidated the role of the cocatalyst HFIP in helping CPA control the reactivity and enantioselectivity of the reaction, demonstrating a new mode of cooperative catalysis.

Synthesis of 1,2,4-oxadiazolidines via [3+2] cycloaddition of nitrones with carbodiimides

An efficient [3+2] cycloaddition of nitrones and carbodiimides has been developed. This 1,3-dipolar cycloaddition features high regioselectivity, mild and metal-free conditions, excellent functional group compatibility, and a broad substrate scope. The X-ray structures of two regio-isomers confirmed the regioselectivity of this transformation.

(3 + 3) Cycloaddition of Oxyallyl Cations with Nitrones: Diastereoselective Access to 1,2-Oxazinanes

Oxyallyl cations are prepared in situ from readily available α-tosyloxy ketones and act as transient electrophilic partners in (3 + 3) cycloaddition with nitrones. Under mild conditions, this method provides a chemoselective and diastereoselective route t

Zinc mediated direct transformation of propargyl N-hydroxylamines to α,β-unsaturated ketones and mechanistic insight

A Lewis acid catalyzed direct transformation of propargyl N-hydroxylamines to α,β-unsaturated ketones in the presence of aqueous Zn(II)-salts has been described. This investigation also provides a novel observation for the stoichiometric role of Zn-halides over what is known to date for catalytic processes. A thorough mechanistic study has been established based on the experiment using18O-labeled water in optimized reaction conditions; the incorporation of18O in the desired product was also substantiated by HRMS. This methodology is also a mild, inexpensive, and an efficient approach for this unusual conversion.

Controlling Asymmetric Remote and Cascade 1,3-Dipolar Cycloaddition Reactions by Organocatalysis

The regio- and stereoselective control of cycloaddition reactions to polyconjugated systems has been demonstrated by applying asymmetric organocatalysis. Reaction of 2,4-dienals with nitrones allows for a highly regio- and stereoselective 1,3-dipolar cycl

One-pot oxidation and rearrangement of propargylamines and in situ pyrazole synthesis

Reported here are procedures for a one-pot oxidation and rearrangement of propargylamines to synthesize enaminones, with supporting mechanistic studies. Also reported are the extended one-pot syntheses of pyrazoles, including celecoxib and various heterocyclic compounds.

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

A magnetoclick imidazolidinone nanocatalyst for asymmetric 1,3-dipolar cycloadditions

A 1,3-dipolar azide-alkyne cycloaddition has been used to prepare a magnetic nanoparticle immobilized MacMillan catalyst that catalyzes the enantioselective 1,3-dipolar cycloaddition between nitrones and α,β-unsaturated aldehydes. The catalyst can be recovered and recycled for five consecutive runs without any significant loss in yields and diastereo- and enantioselectivities of the isoxazolidines. Copyright

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%.

1,3-Dipolar cycloadditions. Part XVII: Experimental and theoretical spectroscopic investigations of C-aryl-N-methyl nitrones

Detailed experimental and theoretical spectroscopic studies of C-aryl-N-methyl nitrones have been reported. The optimized geometries have been calculated by DFT/B3LYP level of theory with 6-31+G(d,p) basis set. The theoretically computed frontier orbital