73025-50-0

Upstream product

• 75-52-5 nitromethane 
• 100-47-0 benzonitrile 
• 16717-64-9 1-azidostyrene 
• 536-74-3 phenylacetylene 
• 614-21-1 2-nitroacetophenone 
• 100-52-7 benzaldehyde 
• 5153-67-3 nitrostyrene 
• 102-96-5 (2-nitroethenyl)benzene 
• 67-62-9 O-Methylhydroxylamin 

Downstream Products

• 94768-22-6 N-(2-nitro-1-phenylethyl)acetamide 
• 941602-11-5 tert-butyl N-(2-nitro-1-phenylethyl)carbamate 
• 614-21-1 2-nitroacetophenone 
• 137102-30-8 (S)-N₁-tert-butoxycarbonyl-1-phenyl-1,2-ethanediamine 
• 1334529-03-1 (R)-5-nitro-4,6-diphenyl-3,4-dihydropyridin-2(1H)-one 
• 95512-77-9 1-amino-2-bromo-2-nitro-1-phenylethylene 
• 95512-76-8 1-amino-2-chloro-2-nitro-1-phenylethylene 

Relevant academic research and scientific papers

Nitrile Hydration Reaction Using Copper Iodide/Cesium Carbonate/DBU in Nitromethane-Water

The catalytic nitrile hydration (amide formation) in a copper iodide/cesium carbonate/1,8-diazabicyclo[5.4.0]undec-7-ene/nitromethane-water system is described. The protocol is robust and reliable; it can be applied to a broad range of substrates with high chemoselectivity.

A Continuous-Flow, Two-Step, Metal-Free Process for the Synthesis of Differently Substituted Chiral 1,2-Diamino Derivatives

The enantioselective organocatalytic reduction of aryl-substituted nitroenamines was successfully performed under continuous-flow conditions. After a preliminary screening with a 10-μL microreactor, to establish the best reaction conditions, the reduction was scaled up in a 0.5-mL mesoreactor, without appreciable loss of enantioselectivity, that remained constantly higher than 90%. The in-flow nitro reduction was also accomplished, either by Raney nickel catalyzed hydrogenation or by a metal-free methodology based on the use of the very inexpensive and readily available reducing agent trichlorosilane. The final aim is to develop a two-step, continuous-flow process for the stereoselective, metal-free, catalytic synthesis of differently functionalized chiral 1,2-diamines.

Quinone-Fused Pyrazoles through 1,3-Dipolar Cycloadditions: Synthesis of Tricyclic Scaffolds and in vitro Cytotoxic Activity Evaluation on Glioblastoma Cancer Cells

A novel and straightforward synthesis of highly substituted isoquinoline-5,8-dione fused tricyclic pyrazoles is reported. The key step of the synthetic sequence is a regioselective, Ag2CO3 promoted, 1,3-dipolar cycloaddition of C-heteroaryl-N-aryl nitrilimines and substituted isoquinoline-5,8-diones. The broad functional group tolerability and mild reaction conditions were found to be suitable for the preparation of a small library of compounds. These scaffolds were designed to interact with multiple biological residues, and two of them, after brief synthetic elaborations, were analyzed by molecular docking studies as potential anticancer drugs. In vitro studies confirmed the potent anticancer effects, showing promising IC50 values as low as 2.5 μm against three different glioblastoma cell lines. Their cytotoxic activity was finally positively correlated to their ability to inhibit PI3K/mTOR kinases, which are responsible for the regulation of diverse cellular processes in human cancer cells.

Copper-Mediated Reactions of Nitriles with Nitromethanes: Aza-Henry Reactions and Nitrile Hydrations

In this study, the first aza-Henry reaction of nitriles with nitromethane in a CuI/Cs2CO3/DBU system is described. The process was conveniently and directly used for the synthesis of β-aminonitroalkenes 2a-x and tolerated aryl-, alkyl-, hetaryl-, alkenyl-, and alkynylnitriles. The resulting aminonitroalkenes 2 could be successfully transformed to the corresponding 2-nitroacetophenones, 2-amino-1-halonitroalkenes, 2-alkylaminonitroalkenes, or 3-nitropyridines. In the presence of H2O, the aza-Henry reaction turned the reaction path to the nitrile hydration to exclusively yield the amides 3a-s.

Radical Enamination of Vinyl Azides: Direct Synthesis of N-Unprotected Enamines

An electron-withdrawing-group-generable radical-induced enamination of vinyl azides is reported, which results in a variety of β-functionalized N-unprotected enamines in a stereoselective manner. A plausible mechanism involving an unusual 1,3-H transfer of in situ generated iminyl radical intermediate was proposed on the basis of experimental results and DFT calculations.

Organocatalytic Enantioselective Transfer Hydrogenation of β-Amino Nitroolefins

The asymmetric organocatalytic transfer hydrogenation of β-acylamino and β-tert-butyloxycarbonylamino nitroolefins has been successfully realised in excellent enantioselectivities and yields (up to >99% ee, 97% yield) with a simple thiourea catalyst and a Hantzsch ester as hydrogen source, giving a direct access to enantiomerically pure β-amino nitroalkanes. (Figure presented.).

INHIBITORS OF Akt ACTIVITY

Invented are novel 1 H-imidazo[4,5-c]pyridin-2-yI compounds, the use of such compounds as inhibitors of protein kinase B activity and in the treatment of cancer and arthritis.

A new synthesis of β-nitroenamines by animation of nitroolefins with methoxyamines

The amination of nitroolefins with methoxyamines in the presence of a base gives β-nitroenamines in good yields.