2570-98-1

Upstream product

• 873-74-5 4-Aminobenzonitrile 
• 925-90-6 ethylmagnesium bromide 
• 35704-19-9 N-(4-cyanophenyl)acetamide 
• 619-72-7 4-nitrobenzonitrile 

Downstream Products

• 125802-53-1 4-(9-Benzyl-2-chloro-9H-purin-6-ylamino)-benzonitrile 
• 143090-18-0 tert-butyl N-(4-cyanophenyl)carbamate 
• 916151-00-3 4-carboxaldehyde-1-(4-cyanophenyl)-1H-1,2,3-triazole 
• 1234896-90-2 C₁₆H₉ClN₄O₂ 
• 862876-05-9 N-(4-cyanophenyl)-2-methyl-2-phenylpropanamide 
• 1400976-49-9 C₂₀H₁₂N₄O₂ 
• 924962-08-3 4-methylquinoline-6-carbonitrile 
• 88485-89-6 4-[(Cyano-phenyl-methyl)-amino]-benzonitrile 
• 373690-68-7 4-cyanophenyl guanidine hydrochloride 
• 124573-84-8 C₁₅H₁₀N₂O₄ 
• 124573-78-0 4-[(Carboxy-phenyl-methyl)-amino]-benzoic acid 

Relevant academic research and scientific papers

Mild N-deacylation of secondary amides by alkylation with organocerium reagents

Secondary amides are a class of highly stable compounds serving as versatile starting materials, intermediates and directing groups (amido groups) in organic synthesis. The direct deacylation of secondary amides to release amines is an important transformation in organic synthesis. Here, we report a protocol for the deacylation of secondary amides and isolation of amines. The method is based on the activation of amides with Tf2O, followed by addition of organocerium reagents, and acidic work-up. The reaction proceeded under mild conditions and afforded the corresponding amines, isolated as their hydrochloride salts, in good yields. In combination with the C-H activation functionalization methodology, the method is applicable to the functionalization of aniline as well as conversion of carboxylic derivatives to functionalized ketones.

Deoxygenation of Nitrous Oxide and Nitro Compounds Using Bis(N-Heterocyclic Silylene)Amido Iron Complexes as Catalysts

Herein, we report the efficient degradation of N2O with a well-defined bis(silylene)amido iron complex as catalyst. The deoxygenation of N2O using the iron silanone complex 4 as a catalyst and pinacolborane (HBpin) as a sacrificial reagent proceeds smoothly at 50 °C to form N2, H2, and (pinB)2O. Mechanistic studies suggest that the iron–silicon cooperativity is the key to this catalytic transformation, which involves N2O activation, H atom transfer, H2 release and oxygenation of the boron sites. This approach has been further developed to enable catalytic reductions of nitro compounds, producing amino-boranes with good functional-group tolerance and excellent chemoselectivity.

Selective and Additive-Free Hydrogenation of Nitroarenes Mediated by a DMSO-Tagged Molecular Cobalt Corrole Catalyst

We report on the first cobalt corrole that effectively mediates the homogeneous hydrogenation of structurally diverse nitroarenes to afford the corresponding amines. The given catalyst is easily assembled prior to use from 4-tert-butylbenzaldehyde and pyrrole followed by metalation of the resulting corrole macrocycle with cobalt(II) acetate. The thus-prepared complex is self-contained in that the hydrogenation protocol is free from the requirement for adding any auxiliary reagent to elicit the catalytic activity of the applied metal complex. Moreover, a containment system is not required for the assembly of the hydrogenation reaction set-up as both the autoclave and the reaction vessels are readily charged under a regular laboratory atmosphere.

JAK2 JH2 Fluorescence Polarization Assay and Crystal Structures for Complexes with Three Small Molecules

A competitive fluorescence polarization (FP) assay is reported for determining binding affinities of probe molecules with the pseudokinase JAK2 JH2 allosteric site. The syntheses of the fluorescent 5 and 6 used in the assay are reported as well as Kd results for 10 compounds, including JNJ7706621, NVP-BSK805, and filgotinib (GLPG0634). X-ray crystal structures of JAK2 JH2 in complex with NVP-BSK805, filgotinib, and diaminopyrimidine 8 elucidate the binding poses.

High graphite N content in nitrogen-doped graphene as an efficient metal-free catalyst for reduction of nitroarenes in water

Four kinds of nitrogen-doped graphene (NG) as metal-free catalysts are synthesized by a one-step hydrothermal reaction and thermal treatment using graphene oxide and urea as precursors. It is found that the reduction of nitroarenes can be catalyzed by using a low NG loading and a small amount of NaBH4 in water with high yield. The type of nitrogen species in NG has an important effect on the reduction reaction. The NG catalyst containing the most graphite N shows the highest catalytic activity during reduction of nitroarenes, which demonstrates that the graphite N of NG plays a key role in impelling this reaction. The reaction mechanism is proven by GC-MS experiments, and DFT calculations reveal the reasons for the graphite N showing better catalytic activity. It is worth noting that no dehalogenation phenomenon occurs during the reduction process for halogen-substituted nitroarenes in contrast to conventional metal catalysts. In addition, the NG catalyst can be simply recycled and efficiently used for eight consecutive runs with no significant decrease in activity.

Iron-catalysed, general and operationally simple formal hydrogenation using Fe(OTf)3 and NaBH4

An operationally simple and environmentally benign formal hydrogenation protocol has been developed using highly abundant iron(iii) salts and an inexpensive, bench stable, stoichiometric reductant, NaBH4, in ethanol, under ambient conditions. This reaction has been applied to the reduction of terminal alkenes (22 examples, up to 95% yield) and nitro-groups (26 examples, up to 95% yield). Deuterium labelling studies indicate that this reaction proceeds via an ionic rather than radical mechanism.

1,2,3-Trimethoxypropane, a glycerol-based solvent with low toxicity: New utilization for the reduction of nitrile, nitro, ester, and acid functional groups with TMDS and a metal catalyst

1,2,3-Trimethoxypropane (1,2,3-TMP) was prepared from glycerol in one step in good yield and selectivity by phase transfer catalysis. According to OECD guidelines, a toxicity study was realized for this compound. It revealed that 1,2,3-TMP has a low acute toxicity, no skin sensitization, no mutagenicity and no ecotoxicity in an aquatic environment. This compound was also used as a solvent for the reduction of organic functions using either aluminium hydride or 1,1,3,3-tetramethyldisiloxane (TMDS) as a benign hydride source. In particular, a new process for the reduction of nitriles to amines in 2-MeTHF and in 1,2,3-TMP was developed, using TMDS in combination with copper triflate (Cu(OTf)2).

Alternative method for the reduction of aromatic nitro to amine using TMDS-iron catalyst system

The system 1,1,3,3-tetramethyldisiloxane (TMDS)/Fe(acac)3 is reported here as a new method to obtain amines from aromatic nitro compounds. Amines are synthetized in a straightforward step and are isolated as hydrochloride salts with good to excellent yields. This system has shown a good selectivity toward aryl-chloride, aryl-bromide, ester, carboxylic acid, and cyano groups. The reduction of alkylnitro compounds was unfortunately not possible using this method, only a mixture of mono and dialkylated amine was obtained.

Iron-catalyzed selective reduction of nitro compounds to amines

An efficient reduction of the nitro group with a catalytic amount of Fe(acac)3 and TMDS in THF at 60 °C affording the corresponding amine is described.