26595-63-1

Upstream product

• 17876-90-3 3-trimethylsilylanisol 
• 90-04-0 2-methoxy-phenylamine 
• 10365-98-7 3-methoxyphenylboronic acid 
• 555-03-3 3-nitroanisole 
• 145490-71-7 2C₄₂H₇₀O₃₅*C₈H₁₁N*C₇H₇NO₃ 
• 536-90-3 m-Anisidine 

Downstream Products

• 73009-69-5 4,5α-epoxy-3,6-dimethoxy-18-(3-methoxy-phenyl)-17-methyl-6β,14-oxaazaethano-morphin-7-ene 
• 76869-88-0 C₉H₁₀N₂O₄ 
• 555-03-3 3-nitroanisole 
• 6933-49-9 2-methoxy-9H-carbazole 
• 6933-50-2 4-methoxy-9H-carbazole 
• 81265-89-6 2-(3-methoxyphenyl)-2H-indazole 
• 62257-15-2 2-fluoro-5-methoxyaniline 

Relevant academic research and scientific papers

Photoswitchable Antagonists for a Precise Spatiotemporal Control of β2-Adrenoceptors

β2-Adrenoceptors (β2-AR) are prototypical G-protein-coupled receptors and important pharmacological targets with relevant roles in physiological processes and diseases. Herein, we introduce Photoazolol-1-3, a series of photoswitchable azobenzene β2-AR ant

Azobioisosteres of Curcumin with Pronounced Activity against Amyloid Aggregation, Intracellular Oxidative Stress, and Neuroinflammation

Many (poly-)phenolic natural products, for example, curcumin and taxifolin, have been studied for their activity against specific hallmarks of neurodegeneration, such as amyloid-β 42 (Aβ42) aggregation and neuroinflammation. Due to their drawbacks, arising from poor pharmacokinetics, rapid metabolism, and even instability in aqueous medium, the biological activity of azobenzene compounds carrying a pharmacophoric catechol group, which have been designed as bioisoteres of curcumin has been examined. Molecular simulations reveal the ability of these compounds to form a hydrophobic cluster with Aβ42, which adopts different folds, affecting the propensity to populate fibril-like conformations. Furthermore, the curcumin bioisosteres exceeded the parent compound in activity against Aβ42 aggregation inhibition, glutamate-induced intracellular oxidative stress in HT22 cells, and neuroinflammation in microglial BV-2 cells. The most active compound prevented apoptosis of HT22 cells at a concentration of 2.5 μm (83 % cell survival), whereas curcumin only showed very low protection at 10 μm (21 % cell survival).

Rhodium-Catalyzed Reaction of Azobenzenes and Nitrosoarenes toward Phenazines

A rhodium-catalyzed annulative reaction between azobenzenes and nitrosoarenes has been developed, leading to a series of phenazines in moderate to good yields. This procedure proceeds with sequential chelation-assisted addition of aryl C-H to nitrosoarenes and ring closure by electrophilic attack of azo group to aryl. During this transformation, the azo group served as not only a traceless directing group but also a building block in the final products.

Anion ligand promoted selective C-F bond reductive elimination enables C(sp2)-H fluorination

A detailed mechanism study on the anion ligand promoted selective C-H bond fluorination is reported. The role of the anion ligand has been clarified by experimental evidence and DFT calculations. Moreover, the nitrate promoted C-F bond reductive elimination enabled a selective C-H bond fluorination of various symmetric and asymmetric azobenzenes to access diverse o-fluoroanilines.

Synthesis of Nitrosobenzene Derivatives via Nitrosodesilylation Reaction

The electrophilic ipso-substitution of trimethylsilyl-substituted benzene derivatives into nitrosobenzene derivatives is reported. The optimization of the reaction conditions was performed for moderately electron-deficient, electron-rich, and sterically hindered starting materials by varying reaction time, temperature, and equivalents of NOBF4. Also, a stable intermediate of the nitrosation reaction could be characterized by 19F NMR which can be assigned to a NO+ adduct with the nitrosobenzene derivative. This complex decomposes upon aqueous workup and liberates the desired nitrosobenzene derivative.

Titania-Supported Gold Nanoparticles Catalyze the Selective Oxidation of Amines into Nitroso Compounds in the Presence of Hydrogen Peroxide

In this article, the catalytic activity of titania-supported gold nanoparticles (Au/TiO2) was studied for the selective oxidation of amines into nitroso compounds using hydrogen peroxide (H2O2). Gold nanoparticles deposited on Degussa P25 polymorphs of titania (TiO2) have been found to promote the selective formation of a variety of nitroso arenes in high yields and selectivities, even in a large-scale synthesis. In contrast, alkyl amines are oxidized to the corresponding oximes under the examined conditions. Kinetic studies indicated that aryl amines substituted with electron-donating groups are oxidized faster than the corresponding amines bearing an electron-withdrawing functionality. A Hammett-type kinetic analysis of a range of para-X-substituted aryl amines implicates an electron transfer (ET) mechanism (ρ=-1.15) for oxidation reactions with concomitant formation of the corresponding N-aryl hydroxylamine as possible intermediate. We also show that the oxidation protocol of aryl amines in the presence of 1,3-cyclohexadiene leads in excellent yields to the corresponding hetero Diels-Alder adducts between the diene and the in situ formed nitrosoarenes.

Enantioselective Nitroso Aldol Reaction Catalyzed by a Chiral Phosphine–Silver Complex

A catalytic asymmetric O-nitroso aldol reaction of alkenyl trifluoroacetates with nitrosoarenes was achieved by using QuinoxP*·AgOAc [(R,R)-QuinoxP* = (–)-(R,R)-2,3-bis(tert-butylmethylphosphino)quinoxaline] as the chiral precatalyst and N,N-diisopropylethylamine as the base precatalyst in the presence of methanol. Optically active α-aminooxy ketones with up to 99 % ee were regioselectively obtained in moderate to high yields by the in situ generated chiral silver enolates.

Cobalt(III)-catalyzed synthesis of indazoles and furans by C-H bond functionalization/addition/cyclization cascades

The development of operationally straightforward and cost-effective routes for the assembly of heterocycles from simple inputs is important for many scientific endeavors, including pharmaceutical, agrochemical, and materials research. In this article we describe the development of a new air-stable cationic Co(III) catalyst for convergent, one-step benchtop syntheses of N-aryl-2H-indazoles and furans by C-H bond additions to aldehydes followed by in situ cyclization and aromatization. Only a substoichiometric amount of AcOH is required as an additive that is both low-cost and convenient to handle. The syntheses of these heterocycles are the first examples of Co(III)-catalyzed additions to aldehydes, and reactions are demonstrated for a variety of aromatic, heteroaromatic, and aliphatic derivatives. The syntheses of both N-aryl-2H-indazoles and furans have been performed on 20 mmol scales and should be readily applicable to larger scales. The reported heterocycle syntheses also demonstrate the use of directing groups that have not previously been applied to Co(III)-catalyzed C-H bond functionalizations. Additionally, the synthesis of furans demonstrates the first example of Co(III)-catalyzed functionalization of alkenyl C-H bonds.

Nitrosation of aryl and heteroaryltrifluoroborates with nitrosonium tetrafluoroborate

Organotrifluoroborates have emerged as an alternative to toxic and air- and moisture-sensitive organometallic species for the synthesis of functionalized aryl and heteroaryl compounds. It has been shown that the trifluoroborate moiety can be easily converted into a variety of different substituents in a late synthetic stage. In this paper, we disclose a mild, selective, and convenient method for the ipso-nitrosation of organotrifluoroborates using nitrosonium tetrafluoroborate (NOBF4). Aryl- and heteroaryltrifluoroborates were converted into the corresponding nitroso products in good to excellent yields. This method proved to be tolerant of a broad range of functional groups.

Selective photoreduction of nitrophenyl ethers by amines in ternary β-cyclodextrin complexes. A spectroscopic and mechanistic study

The photoreduction of nitrophenyl ethers by amines has been studied in aqueous solution in the presence of β-cyclodextrin (β-CD), and in ternary β-cyclodextrin complexes in the solid state. NMR (NOESY) and induced circular dichroism (ICD) studies in solution suggest the operation of a cooperative effect by the amine in the complexation of the nitrophenyl ether by the β-CD, evidencing the existence of interactions between complementary groups that govern the structure of the ternary complexes. Irradiation of the solutions shows an inhibitory effect of the β-CD, together with a significant increase in the chimioselectivity of the photoreaction. This tendency is confirmed by irradiation of the solid ternary complexes that show a complete selectivity, only producing the nitroso derivative. A time-resolved diffuse reflectance laser flash photolysis (DRLFP) mechanistic study on the solid complexes has demonstrated that in the ternary β-CD complexes, the evolution of the first transient (assigned to the triplet excited state of the nitropheny ether) is completely different than in solution or in mechanical cellulose mixtures, this approach being a very valuable tool to investigate bimolecular photoinduced reactions difficult to study in solution due to the existence of other competitive processes.