854602-03-2

Upstream product

• 612-23-7 2-nitrobenzyl chloride 
• 106-49-0 p-toluidine 
• 552-89-6 2-nitro-benzaldehyde 
• 17064-82-3 4-methyl-(2-nitrobenzylidene)aniline 

Downstream Products

• 3682-73-3 2-(4-methylphenyl)-2H-indazole 
• 857002-47-2 N-(2-aminobenzyl)-4-methylaniline 
• 723289-60-9 4-methyl-2,6,N-trinitro-N-(2-nitro-benzyl)-aniline 
• 94242-54-3 3-(4-carboxylphenyl)quinazolin-4(3H)-one 
• 127662-26-4 3-p-tolyl-1,2,3,4-tetrahydro-quinazoline 
• 24122-33-6 3-(4-methylphenyl)-4(3H)-quinazolinone 

Relevant academic research and scientific papers

Rhodium catalysts with cofactor mimics for the biomimetic reduction of CN bonds

A strategy based on the cooperation between metal and bonded cofactor mimics was applied to the transfer hydrogenation of CN bonds. We designed and synthesized a rhodium complex containing a 1,3-dimethylbenzoimidazole moiety, which could transfer hydride from a rhodium center to imine substrates in a biomimetic way. Under both transfer hydrogenation and reductive amination reaction conditions, the catalyst exhibited good selectivity towards CN bonds. With the catalyst, 34 imines were transfer hydrogenated to corresponding amines and a key intermediate of retigabine was prepared via reductive amination in a greener way. According to the NMR observations and isotope experiments, a plausible mechanism for this biomimetic reduction of CN bonds were proposed.

Facile synthesis of 4-substituted 1,2,4,5-tetrahydro-1,4-benzodiazepin-3-ones by reductive cyclization of 2-chloro-N-(2-nitrobenzyl)acetamides

A facile and efficient method was developed for the synthesis of 1,2,4,5-tetrahydro-1,4-benzodiazepine-3-ones from 2-chloro-N-(2-nitrobenzyl)acetamides through a reductive cyclization using iron-ammonium chloride in ethanol–water in good yields. This method provides a simple approach to these benzodiazepine-3-ones which are of high value in the field of medicinal chemistry research.

Integration of Bromine and Cyanogen Bromide Generators for the Continuous-Flow Synthesis of Cyclic Guanidines

A continuous-flow process for the in situ on-demand generation of cyanogen bromide (BrCN) from bromine and potassium cyanide that makes use of membrane-separation technology is described. In order to circumvent the handling, storage, and transportation of elemental bromine, a continuous bromine generator using bromate–bromide synproportionation can optionally be attached upstream. Monitoring and quantification of BrCN generation was enabled through the implementation of in-line FTIR technology. With the Br2 and BrCN generators connected in series, 0.2 mmol BrCN per minute was produced, which corresponds to a 0.8 m solution of BrCN in dichloromethane. The modular Br2/BrCN generator was employed for the synthesis of a diverse set of biologically relevant five- and six-membered cyclic amidines and guanidines. The set-up can either be operated in a fully integrated continuous format or, where reactive crystallization is beneficial, in semi-batch mode.

Preparation of arylamines form aldehydes by Zn(BH4)2/MgBr2

Reductive aminationa varietyof aldehydes with different anilines has been performed by Zn(BH4)2/MgBr2as reducing system in THF at room temperature in high to excellent yields of the corresponding secondary amines (80-90%).

Solvent-free mechanochemical and one-pot reductive benzylizations of malononitrile and 4-methylaniline using Hantzsch 1,4-dihydropyridine as the reductantt

The properties of Hantzsch 1,4-dihydropyridine, which possesses excellent reducibility, were investigated. The synthesis of benzyl malononitriles and anilines were also studied. Direct reductive benzylizations of malononitrile and 4-methylaniline by aromatic aldehydes were achieved using a Hantzsch 1,4-dihydropyridine as the reductant. It was observed that there is no need for the separation of the in situ generated benzylidene malononitriles and p-tolylamines.