61298-18-8

Upstream product

• 89-98-5 2-chloro-benzaldehyde 
• 104-94-9 4-methoxy-aniline 
• 17099-11-5 N-(4-methoxyphenyl)-2-chlorobenzylidenimine 
• 2039-87-4 2-chlorostyrene 
• 2101-87-3 p-methoxy-phenylazide 
• 83306-64-3 (E)-1-(2-chlorophenyl)-N-(4-methoxyphenyl)methanimine 

Downstream Products

• 1184446-14-7 2-(2-chlorophenyl)-2-((4-methoxyphenyl)amino)acetonitrile 
• 1507344-46-8 C₁₅H₁₃ClN₂O 

Relevant academic research and scientific papers

Iron-Catalyzed Nitrene Transfer Reaction of 4-Hydroxystilbenes with Aryl Azides: Synthesis of Imines via C=C Bond Cleavage

C=C bond breaking to access the C=N bond remains an underdeveloped area. A new protocol for C=C bond cleavage of alkenes under nonoxidative conditions to produce imines via an iron-catalyzed nitrene transfer reaction of 4-hydroxystilbenes with aryl azides is reported. The success of various sequential one-pot reactions reveals that the good compatibility of this method makes it very attractive for synthetic applications. On the basis of experimental observations, a plausible reaction mechanism is also proposed.

Enhanced Catalytic Activity of Oxygen-Tethered IrIII NHC Complexes in Aqueous Transfer Hydrogenative Reductive Amination Reactions: Experimental Kinetic and Mechanistic Study

The synthesis and characterization of seven new IrIII complexes containing o-phenoxide or o-naphthoxide chelated N-heterocyclic carbene ligands is reported herein. The crystal structures of six of the complexes have been determined. These complexes efficiently catalyze the transfer hydrogenative reductive amination (RA) of carbonyls and amines in water. Amongst the complexes tested, the introduction of o-naphthoxide on a nitrogen atom of imidazole based NHC ligand greatly increased the catalytic activity. The catalytic system has a broad substrate scope, which allows the synthesis of a variety of amines in excellent yields and with high turnover numbers up to 490 (for ketones) and 14800 (for aldehydes). The mechanism of aqueous RA reaction with an o-aryloxide chelated NHC-IrIII catalyst has been investigated by NMR spectroscopy and kinetic measurements. These studies suggest that the transfer hydrogenation (TH) is turnover-limited by the hydride formation step. As a result of the 1H NMR studies, the higher catalytic activity of o-naphthoxide chelated catalyst (3 g) over o-phenoxide chelated one (3 b) can be attributed partly due to the faster formation of an iridium hydride, the key intermediate in the RA reactions.

Ruthenium-catalyzed reductive amination without an external hydrogen source

A ruthenium-catalyzed reductive amination without an external hydrogen source has been developed using carbon monoxide as the reductant and ruthenium(III) chloride (0.008-2 mol %) as the catalyst. The method was applied to the synthesis of antianxiety agent ladasten.

Solvent- and catalyst-free direct reductive amination of aldehydes and ketones with Hantzsch ester: Synthesis of secondary and tertiary amines

A facile and rapid method for the parallel synthesis of a series of secondary and tertiary amines by the direct reductive amination of aldehydes and ketones with Hantzsch ester under solvent- and catalyst-free has been developed. The scope and limitation of this method are described.

Transfer hydrogenation of imines with carboxyl-tailed benzothiazoline as readily removable hydrogen donor

A benzothiazoline bearing 4-carboxyphenyl group at 2-position was developed as an efficient hydrogen donor for the transfer hydrogenation reaction. Introduction of the carboxyl group significantly facilitated the removal of the residual benzothiazoline an

Br?nsted acid catalyzed reductive amination with benzothiazoline as a highly efficient hydrogen donor

Reductive amination of aldehyde and amine proceeded smoothly in the presence of benzothiazoline as efficient hydrogen source by means of 20 mol% trifluoroacetic acid to give the corresponding amines in excellent yields. Hydrogen-donor abilities of benzothiazoline, benzimidazoline, and benzoxazoline were compared. Georg Thieme Verlag Stuttgart - New York.

Inexpensive protocol for reduction of imines to amines using polymethylhydrosiloxane (PMHS)

Amines have been prepared by reduction of imines using inexpensive Polymethylhydrosiloxane (PMHS) a ; a hydride source activated by ZnCl2.

Analgesic compositions containing 1,2-dihydro-2-oxoquinol-4-ylpropionic acid derivatives

Novel 1,2-dihydro-2-oxoquinol-4-ylalkanoic acid derivatives bearing a variety of substituents on the quinoline nucleus but including, at position 1, an aromatic radical linked directly or through a C1-4 -alkylene or a C2-4 -alkenylene radical. Representative compounds of the invention are 1-(3,4-dichlorobenzyl)-3-methyl-1,2-dihydro-2-oxoquinol-4-ylacetic acid and α-(1-benzyl-1,2-dihydro-2-oxoquinol-4-yl)propionic acid. The compounds possess anti-inflammatory or analgesic properties, or are inhibitors of the enzyme aldose reductase.