57527-58-9

Upstream product

• 100-52-7 benzaldehyde 
• 75-31-0 isopropylamine 
• 6852-56-8 N-benzylideneisopropylamine 
• 27845-51-8 (E)-N-benzylidenepropan-2-amine 

Downstream Products

• 5440-69-7 N-isopropylbenzamide 
• 50484-16-7 4-butyl-2-isopropyl-3-phenyl-[1,2,4]oxadiazolidin-5-one 
• 50484-11-2 2-benzhydrylidene-3-isopropyl-5,5-diphenyl-oxazolidin-4-one 
• 50506-93-9 5-isopropylimino-2,4-diphenyl-[1,2,4]thiadiazolidine-3-thione 
• 50506-89-3 4-isopropyl-2-phenyl-5-phenylimino-[1,2,4]thiadiazolidine-3-thione 
• 50484-15-6 2-isopropyl-3,4-diphenyl-[1,2,4]oxadiazolidin-5-one 

Relevant academic research and scientific papers

Weak base-promoted selective rearrangement of oxaziridines to amidesviavisible-light photoredox catalysis

The selective rearrangement of oxaziridines to amidesviaa single electron transfer (SET) pathway is unexplored. In this study, we present a weak base-promoted selective rearrangement of oxaziridines to amidesviavisible-light photoredox catalysis. The developed method shows excellent functional group tolerance with a broad substrate scope and good to excellent yields. Furthermore, control experiments and density functional theory (DFT) calculations are performed to gain insight into the reactivity and selectivity.

Atom economical synthesis of: N -alkylbenzamides via the iron(III) sulfate catalyzed rearrangement of 2-alkyl-3-aryloxaziridines in water and in the presence of a surfactant

A green and mild synthetic route to N-alkylbenzamides involves eco-friendly one pot synthesis of 2-alkyl-3-aryloxaziridines from N-alkylamines and benzaldehydes followed by iron(iii) sulfate catalyzed rearrangement to the corresponding amides in water as the solvent and in the presence of sodium dodecyl sulfate as the surfactant. This green approach affords N-alkylbenzamides in high overall yields under simple and minimum manipulation.

Hydrogen peroxide/dimethyl carbonate: A green system for epoxidation of: N -alkylimines and N -sulfonylimines. One-pot synthesis of N -alkyloxaziridines from N -alkylamines and (hetero)aromatic aldehydes

A green method for epoxidation of imines using an environmentally benign oxidant system, H2O2/dimethyl carbonate, was developed. N-Alkyloxaziridines were prepared in high yields from N-alkylamines and (hetero)aromatic aldehydes in one-pot fashion, whereas N-sulfonyloxaziridines have been prepared by using the same oxidant system and 5 mol% of Zn(OAc)2·2H2O as catalyst.

Ring Expansion of Donor-Acceptor Cyclopropane via Substituent Controlled Selective N-Transfer of Oxaziridine: Synthetic and Mechanistic Insights

A distinctive N-substituent controlled electrophilic N-transfer of oxaziridines with donor-acceptor cyclopropanes in the presence of MgI2 is reported. Contrary to earlier reports, the oxaziridine having bulkier N-substituents can also give N-transferred product instead of the O-transferred one. Interestingly, the oxaziridines having α-H containing N-substituents lead to the pyrrolidine derivatives through [3 + 2] cycloaddition. A mechanistic reasoning for this divergent reactivity is depicted by density functional theory calculations and validated through energy decomposition analysis.

Synthesis of dihydrobenzisoxazoles by the [3 + 2] cycloaddition of arynes and oxaziridines

Dihydrobenzisoxazoles are readily prepared in good yields by the [3 + 2] cycloaddition of oxaziridines and arynes. The reaction involves an unusual cleavage of the C-O bond of the oxaziridine and tolerates a variety of substituents on the oxaziridine and the o-(trimethylsilyl)aryl triflate to form aryl-, heteroaryl-, alkyl-, and naphthyl-substituted dihydrobenzisoxazoles. The resulting halogen-substituted dihydrobenzisoxazoles are readily elaborated to more complex products using palladium-catalyzed crossing-coupling processes.

Synthesis of stable isoxazolines by [3+2] cycloaddition of oxaziridines with alkynes

N-Alkyl substituted oxaziridines undergo a [3+2] cycloaddition reaction with a variety of terminal alkynes to give the product isoxazolines, whose stability appears to depend on the electronic properties of the groups on the C-3 and C-5 positions. The presence of an electron withdrawing group on C-5 and/or an electron donating group on C-3 causes isomerization of the isoxazolines to β-amino enones.

[Bmim]BF4-immobilized rhenium-catalyzed highly efficient oxygenation of aldimines to oxaziridines using solid peroxides as oxidants

Various rhenium-based catalysts immobilized in [bmim]BF4 were found to be efficient for oxygenation of various aldimines to the corresponding oxaziridines in excellent yields under mild conditions using solid peroxides like UHP, SPC and SPB as oxidants. Among the various rhenium-based catalysts studied, MTO was found to be most efficient. The reusability and recyclability of MTO immobilized in [bmim]BF4 was established by using it for three subsequent cycles for oxygenation of benzylidine-tert-butylamine using UHP as oxidant.

An environmentally friendly oxidation system for the selective oxygenation of aldimines to oxaziridines with anhydrous TBHP and alumina-supported MoO 3 as a recyclable heterogeneous catalyst

A highly efficient and selective protocol for the oxygenation of various aldimines to oxaziridines, which proceeds in excellent yields with enhanced selectivity by using alumina-supported M0O3 as a recyclable heterogeneous catalyst and anhydrous TBHP as the ultimate oxidant, is described. Wiley-VCH Verlag GmbH & Co. KGaA, 2007.

Activation of oxaziridines by Lewis acids: Application in enantioselective sulfoxidation

(Chemical Equation Presented). The preparation of new and easily accessible chiral N-alkyloxaziridines for asymmetric sulfides oxidation was investigated. Most significantly, we report here that inert N-alkyloxaziridines can be activated by Lewis acids to

An inexpensive and selective oxygenation of N-alkyl imines to oxaziridines

A range of N-alkyl imines was oxidised to corresponding oxaziridines in a highly selective manner with sodium tungstate-30% H2O2 in acetonitrile under mild conditions.