22661-26-3

Upstream product

• 66-99-9 β-naphthaldehyde 
• 622-30-0 N-benzyl hydroxylalmine 
• 29601-98-7 N-benzylhydroxylamine hydrochloride 
• 932-90-1 Benzaldoxime 
• 141120-50-5 (E)-N-benzyl-1-(naphthalen-2-yl)methanimine 

Downstream Products

• 1255534-69-0 (3S,4R,5S)-(2-benzyl-5-methyl-3-(naphthalen-2-yl)isoxazolidin-4-yl)(3,5-dimethyl-1H-pyrazol-1-yl)methanone 
• 1255534-53-2 (R)-(2-benzyl-5-methyl-3-(naphthalen-2-yl)-2,3-dihydroisoxazol-4-yl)(3,5-dimethyl-1H-pyrazol-1-yl)methanone 
• 1255534-70-3 (3S,4R)-(2-benzyl-3-(naphthalen-2-yl)isoxazolidin-4-yl)(3,5-dimethyl-1H-pyrazol-1-yl)methanone 
• 1255534-63-4 (R)-(2-benzyl-3-(naphthalen-2-yl)-2,3-dihydroisoxazol-4-yl)(3,5-dimethyl-1H-pyrazol-1-yl)methanone 
• 1255534-65-6 (R)-(2-benzyl-5-(chloromethyl)-3-(naphthalen-2-yl)-2,3-dihydroisoxazol-4-yl)(3,5-dimethyl-1H-pyrazol-1-yl)methanone 

Relevant academic research and scientific papers

Accessing benzooxadiazepines: Via formal [4 + 3] cycloadditions of aza- o -quinone methides with nitrones

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.

α,β-Unsaturated Amides as Dipolarophiles: Catalytic Asymmetric exo-Selective 1,3-Dipolar Cycloaddition with Nitrones

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.

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

Efficient combination of task-specific ionic liquid and microwave dielectric heating applied to synthesis of a large variety of nitrones

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

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).

Catalytic oxidation of imines based on methyltrioxorhenium/urea hydrogen peroxide: A mild and easy chemo- and regioselective entry to nitrones

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

Enantioselective nitrone cycloadditions of α,β-unsaturated 2-acyl imidazoles catalyzed by bis(oxazolinyl)pyridine-cerium(IV) triflate complexes

Enantioselective nitrone cycloadditions with β-substituted α,β-unsaturated 2-acyl imidazoles catalyzed by bis(oxazolinyl) pyridine-cerium(IV) triflate complexes 1 have been reported. The isoxazolidine products were efficiently transformed into densely functionalized β′-hydroxy-β-amino acid derivatives.

Asymmetric 1,3-dipolar cycloaddition reaction of nitrones and acrolein with a bis-titanium catalyst as chiral Lewis acid

A μ-oxo-type chiral bis-Ti(IV) oxide (S,S)-1 can be successfully utilized in the asymmetric 1,3-dipolar cycloaddition reactions between various nitrones 2 and acrolein to give the corresponding isoxazolidines with high to excellent enantioselectivities. F