27895-80-3

Upstream product

• 99-61-6 3-nitro-benzaldehyde 
• 75-31-0 isopropylamine 
• 110079-32-8 C₁₀H₁₃ClN₂O₂ 

Downstream Products

• 90390-05-9 Isopropyl-(3-nitro-benzyl)-amine 
• 117617-29-5 (4S,5S)-4-(3-Nitro-phenyl)-2-oxy-4,5-dihydro-isoxazole-3,5-dicarboxylic acid diethyl ester 

Relevant academic research and scientific papers

Microwave-assisted diastereoselective two-step three-component synthesis for rapid access to drug-like libraries of substituted 3-amino-β-lactams

Large, diverse compound libraries are an essential requisite in target-based drug development. In this work, a robust microwave-assisted synthesis for the diastereoselective generation of 3-saccharinyl-trans-β-lactams is reported. The method is optimised

Thiazolidinones derived from dynamic systemic resolution of complex reversible-reaction networks

A complex dynamic system based on a network of multiple reversible reactions has been established. The network was applied to a dynamic systemic resolution protocol based on kinetically controlled lipase-catalyzed transformations. This resulted in the formation of cyclized products, where two thiazolidinone compounds were efficiently produced from a range of potential transformations.

Kinetics and mechanism of the Pudovik reaction in the azomethine series: I. Addition of dimethyl hydrogen phosphite to N-isopropylbenzalimines

For a series of phenyl-substituted N-isopropylbenzalimines, the effect of substituent on their capability to add dimethyl hydrogen phosphite was studied qualitatively in the condensed phase (DTA) and quantitatively (with determination of the kinetic and activation parameters) in 2-propanol solutions with spectrophotometric monitoring of the reaction. A reaction mechanism was proposed, involving formation of a highly organized four-membered transition state.

Reactions of N-Chloro-N-alkylbenzylamines with Amines in Acetonitrile. Origin of Steric Effect in Imine-Forming Elimination

Reaction of N-chloro-N-alkylbenzylamines in which the alkyl group is Me, Et, i-Pr, sec-Bu, and t-Bu with MeNH2 and Et2NH in MeCN have been studied kinetically.The eliminations are quantitative and regiospecific, producing only N-benzylidenealkylamines.The relative rates of elimination for Me/Et/i-Pr/sec-Bu/t-Bu alkyl substituents are 1/0.6/0.4/0.3/0.1 with MeNH2 and 1/0.5/0.3/0.2/0.03 with Et2NH, respectively.Comparison with published data reveals that Charton's value for the imine-forming elimination decreases with the variation of the base-solvent from MeONa-MeOH to MeNH2-MeCN but increases when the base is changed from MeNH2 to Et2NH.For a given base, Hammett ρ and kH/kD values decrease and the ΔH(excit.) and ΔS(excit.) values increase with bulkier alkyl substituents.From these results, the origin of the steric effect in imine-forming elimination is attributed to the repulsive interaction between the alkyl group and the base in the transition state.

A Convenient One-Pot Synthesis of 4-Substituted 3,5-Bis(alkoxycarbonyl)-4,5-dihydroisoxazole 2-Oxides from Aldehydes and Nitroacetic Esters in a Solid-Liquid Reaction System and Subsequent Deoxygenation

4-Substituted 3,5-bis(alkoxycarbonyl)-4,5-dihydroisoxazole 2-oxides are obtained from nitroacetic esters and imines which are prepared from aldehydes and isopropylamine in the presence of molecular sieves.Reduction of the N-oxides with trimethyl phosphite

Reactions of N-Chlorobenzylalkylamines with Sodium Methoxide in Methanol. Steric Effects in Elimination Reactions

Reactions of N-chlorobenzylalkylamines in which the alkyl group is Me, Et, i-Pr, t-Bu, and sec-Bu with MeONa-MeOH have been investigated kinetically.The eliminations are quantitative and regiospecific, producing only benzylidenealkylamines.The reactions are first order in base and first order in substrate, and an E2 mechanism is evident.The relative rates of elimination at 25 deg C are 1/0.5/0.3/0.2/0.01 for Me/Et/i-Pr/sec-Bu/t-Bu alkyl substituents, respectively.The results are attributed to repulsive interaction between the alkyl group and the base in the transition state.Hammett ρ and kH/kD values decreased, but the ΔH(excit.) and ΔS(excit.) values increased with bulkier alkyl substituents.Changes in the transition-state parameters with the substrate steric effect are interpreted with variation in structure of the imine-forming transition states.

Benzylamines: Synthesis and evaluation of antimycobacterial properties

The synthesis of benzylamines with various N-alkyl chains and substituents in the aromatic system as well as their evaluation on Mycobacterium tuberculosis H 37 Ra are described. The most active compounds in this test, N-methyl-3-chlorobenzylamine (MIC 10.2 μg/mL), N-methyl-3,5-dichlorobenzylamine (93, MIC 10.2 μg/mL), and N-butyl-3,5-difluorobenzylamine (MIC 6.4 μg/mL), also exhibited a marked inhibitory effect on Mycobacterium marinum and Mycobacterium lufu used for the determination of antileprotic properties. The combination of 93 with aminosalicylic acid, streptomycin, or dapsone exert marked supra-additive effects on M. tuberculosis H 37 Ra.