18731-45-8

Upstream product

• 75-52-5 nitromethane 
• 99-61-6 3-nitro-benzaldehyde 

Downstream Products

• 618-95-1 methyl 3-nitrobenzoate 
• 14367-80-7 2-nitro-1-(3-nitrophenyl)ethan-1-one 
• 854180-09-9 2-nitro-1-(3-nitrophenyl)ethyl acetate 
• 1336918-17-2 (R)-2-nitro-1-(3-nitrophenyl)ethyl acetate 
• 882-26-8 (E)-1-nitro-3-(2-nitrovinyl)benzene 
• 20105-50-4 (+/-)-2-(m-Amino-phenyl)-2-phenyl-ethylamin 
• 882-26-8 3-nitro-β-nitrostyrene 

Relevant academic research and scientific papers

Chiral oxazoline ligands with two different six-membered azaheteroaromatic rings - Synthesis and application in the Cu-catalyzed nitroaldol reaction

Synthesis and catalytic activity of chiral ligands 5,6-diphenyl-3-{3-[(4S/R)-4-R/Ar-4,5-dihydro-1,3-oxazol-2-yl]pyridin-2-yl}amino-1,2,4-triazines 2 and their analogs 3 possessing an N-oxide function in the pyridine ring are described. The pivotal step in the synthesis of ligands 2 is the Buchwald-Hartwig Pd-catalyzed cross-coupling reaction between 3-bromo-5,6-diphenyl-1,2,4-triazine (7a) and enantiopure 3-(4,5-dihydro-1,3-oxazol-2-yl)pyridin-2-amines 6a-d. Aromatic nucleophilic substitution of chlorine in 3-chloro-5,6-diphenyl-1,2,4-triazine (7b) with 3-(4,5-dihydro-1,3-oxazol-2-yl)pyridin-2-amine 1-oxides 12 was investigated as the key reaction in the synthesis of ligands 3. Two undesired derivatives 13 or 14, resulting from unexpected reactions of 3, were isolated depending on reaction conditions. Compounds 2 and 3 as well as the side products 13 and 14 were screened as chiral ligands in the copper catalyzed enatioselective nitroaldol reaction.

Structural characterization of copper complexes with chiral 1,2,4-triazine-oxazoline ligands

The crystal structure determination of oxazoline-1,2,4-triazine ligand 1f and pyridine-oxazoline ligand 2g was used to analyze their conformational preferences when forming complexes with metals. Proton nuclear magnetic resonance (1H NMR), electrospray ionization mass spectrometry and UV-vis spectroscopy as well as theoretical calculation using molecular mechanics (MM) were adopted to study the composition and geometry of oxazoline-1,2,4-triazine ligands 1 complexes with copper(II) acetate monohydrate. The study revealed that during the complexation, (i) Cu(II) ion is reduced to Cu(I) upon the ligand-to-metal charge transfer transition and (ii) the ligands form with copper(I) 2:1 (L:Cu) complexes of tetrahedral geometry. On the basis of the findings, the catalytic cycle and the active transition state for the enantioselective nitroaldol reaction (the Henry reaction) catalyzed by 1-Cu are proposed.

Highly efficient nanosized mesoporous CuMgAl ternary oxide catalyst

Highly efficient nanosized mesoporous CuMgAl ternary oxide catalysts are provided.

Polymeric nanoassembly of imine functionalized magnetite for loading copper salts to catalyze Henry and A3-coupling reactions

Poly(ethylenimine) was grafted on the magnetite (Fe3O4) nanoparticles, and subsequently reacted with different aldehydes to form the imine functionalities (Fe3O4-Imine NPs). Thus formed Fe3O4/su

Synthesis of nitroaldols through the Henry reaction using a copper(II)–Schiff base complex anchored on magnetite nanoparticles as a heterogeneous nanocatalyst

A Cu(II)-Schiff base complex supported on functionalized Fe3O4 magnetic nanoparticles (MNPs@Salen-Cu(II)) was obtained as a new heterogeneous nanocatalyst. The nanocomposite materials were characterized by vibrating sample magnetometer (VSM), X-ray diffraction (XRD), scanning electron microscopy (SEM), energy dispersive X-ray (EDX), Fourier transform infrared spectroscopy (FT-IR), and thermogravimetric analysis (TGA). The catalyst was used in the Henry reaction in order to accomplish one-pot synthesis of nitroaldol derivatives in green conditions. This nanocatalyst can be easily separated from media of reaction using an external magnet and reused several times without loss of its catalytic activity. Furthermore, the non-toxicity of the catalysts and the high yield of the products are other advantages of this method.

Design, synthesis and structure-activity evaluation of novel 2-pyridone-based inhibitors of α-synuclein aggregation with potentially improved BBB permeability

The treatment of Parkinson's disease (PD), the second most common neurodegenerative human disorder, continues to be symptomatic. Development of drugs able to stop or at least slowdown PD progression would benefit several million people worldwide. SynuClea

Accelerating the optimization of enzyme-catalyzed synthesis conditionsviamachine learning and reactivity descriptors

Enzyme-catalyzed synthesis reactions are of crucial importance for a wide range of applications. An accurate and rapid selection of optimal synthesis conditions is crucial and challenging for both human knowledge and computer predictions. In this work, a

One-Pot Enzyme Cascade Catalyzed Asymmetrization of Primary Alcohols: Synthesis of Enantiocomplementary Chiral β-Nitroalcohols

Biocatalytic asymmetrization of inexpensive and stable primary alcohols to prepare enantioenriched β-nitroalcohols is an important development in green chemistry for the production of chiral pharmaceutical intermediates. Herein, we report a one-pot, two-step cascade reaction sequence in which first benzylic alcohols were oxidized to produce corresponding benzaldehydes using horse liver alcohol dehydrogenase (HLADH). The in situ generated aldehydes were then reacted in a biphasic medium with nitromethane by Arabidopsis thaliana hydroxynitrile lyase (AtHNL) or Baliospermum montanum HNL (BmHNL) catalyzed Henry reaction to produce stereoselective β-nitroalcohols with (R) or (S) configuration, respectively. Using HLADH-AtHNL, (R)-β-nitroalcohols were obtained in up to 64% conversion, and HLADH-BmHNL, (S)-β-nitroalcohols in up to 70% conversion, while in both cases excellent stereoselectivity (up to >99% ee) was achieved. The concept was proven by functionalization of sp3 C?H bond of ten simple achiral benzylic alcohols to enantiocomplementary chiral β-nitroalcohols. (Figure presented.).

A urea-containing metal-organic framework as a multifunctional heterogeneous hydrogen bond-donating catalyst

A urea-containing metal-organic framework (MOF) was synthesized from a V-shaped dicarboxylate ligand and Cu(II) ions. As the undesirable self-aggregation of the urea moiety has been prohibited in the framework, this MOF can act as a heterogeneous hydrogen

Waste-to-useful: A biowaste-derived heterogeneous catalyst for a green and sustainable Henry reaction

Owing to the depletion of resources coupled with increasing waste generation, the conversion of waste biomass to value-added materials has gained interest. Here, we report for the first time the application of Musa acuminata (banana) peel ash (MAPA) as a heterogeneous catalyst for C-C bond formation via a Henry reaction under solvent-free conditions at ambient temperature. The catalyst was well characterized using different analytical techniques like FT-IR, SEM, TEM-EDS, XRD, XRF, XPS, BET and TGA, along with basicity determination by a Hammett indicator test and titration method. An excellent yield of nitroalcohol was obtained within 15-30 minutes. No dehydrated product was observed. The catalyst used in these studies has the advantage of being a waste material and is hence low-cost, easily prepared, recyclable and environmentally friendly. In addition, the use of a biogenic renewable catalyst, its atom economy, and room temperature and solvent-free reaction conditions and the avoidance of column chromatography make the protocol highly significant from green and sustainable chemistry perspectives.