1197-48-4

Upstream product

• 99840-51-4 2-benzylamino-2-methylpropionitrile 
• 45579-91-7 benzylamine hydroiodide 
• 67-64-1 acetone 
• 100-46-9 benzylamine 
• 67-63-0 isopropyl alcohol 
• 100-47-0 benzonitrile 
• 78-84-2 isobutyraldehyde 
• 1077-18-5 N-benzylidenebutan-1-amine 

Downstream Products

• 144863-24-1 N-Benzyl-N-isopropenyl-2-chloropyridine-3-carboxamide 
• 124716-35-4 (R)-1-Benzyl-3-((R)-2,2-dimethyl-4-phenyl-oxazolidin-3-yl)-4,4-dimethyl-azetidin-2-one 
• 124716-36-5 (S)-1-Benzyl-3-((R)-2,2-dimethyl-4-phenyl-oxazolidin-3-yl)-4,4-dimethyl-azetidin-2-one 
• 51137-49-6 methyl N-isopropenyl-N-benzylcarbamate 
• 188302-43-4 N-benzyl-2-methylpent-4-en-2-ylamine 
• 361521-48-4 tert-butyl benzyl(prop-1-en-2-yl)carbamate 
• 75359-72-7 acetonyl-2 cyclopentanone 
• 124716-46-7 1-benzyl-4,4-dimethyl-β-azetidinone 
• 124716-45-6 1-benzyl-4,4-dimethyl-β-azetidinone 

Relevant academic research and scientific papers

High-Throughput reaction optimisation and activity screening of ferrocene-based lewis acid-catalyst complexes by using continuous-flow reaction detection mass spectrometry

Optimising synthetic conversions and assessing catalyst performance is a tedious and laborious endeavour. Herein, we present an automated alternative to the commonly applied sequential approaches that are used to increase catalyst discovery process efficiencies by increasing the number of entities that can be tested. This new approach combines conversion of the reactants and determination of product formation into a single comprehensive reaction detection system that can be operated with minimal catalyst and reactant consumption. With this approach, rudimentary reaction conditions can be quickly optimised and the same system can then be used to screen for the optimal homogenous catalyst in a selected solution-phase synthetic conversion. The system, which is composed of standard HPLC components, can be used to screen catalyst libraries at a repetition rate of five minutes and can be run unsupervised. The sensitive mass spectrometric detection that is implemented in the reaction detection methodology can be used for the simultaneous monitoring of reactants, catalysts and product ions. In the experiments, the three-component reaction that gives a substituted 2imidazoline was optimised. Afterwards, the same method was used to assess a library of ferrocene-based Lewis acid catalysts for performance in the aforementioned conversion in six different solvents. We demonstrate the feasibility of using this methodology to directly compare the performance results obtained in different solvents by calibrating the solvent-specific MS responses.

Modular Photocatalytic Synthesis of α-Trialkyl-α-Tertiary Amines

Molecules displaying an α-trialkyl-α-tertiary amine motif provide access to an important and versatile area of biologically relevant chemical space but are challenging to access through existing synthetic methods. Here, we report an operationally straightforward, multicomponent protocol for the synthesis of a range of functionally and structurally diverse α-trialkyl-α-tertiary amines, which makes use of three readily available components: dialkyl ketones, benzylamines, and alkenes. The strategy relies on the of use visible-light-mediated photocatalysis with readily available Ir(III) complexes to bring about single-electron reduction of an all-alkyl ketimine species to an α-amino radical intermediate; the α-amino radical undergoes Giese-type addition with a variety of alkenes to forge the α-trialkyl-α-tertiary amine center. The mechanism of this process is believed to proceed through an overall redox neutral pathway that involves photocatalytic redox-relay of the imine, generated from the starting amine-ketone condensation, through to an imine-derived product. This is possible because the presence of a benzylic amine component in the intermediate scaffold drives a 1,5-hydrogen atom transfer step after the Giese addition to form a stable benzylic α-amino radical, which is able to close the photocatalytic cycle. These studies detail the evolution of the reaction platform, an extensive investigation of the substrate scope, and preliminary investigation of some of the mechanistic features of this distinct photocatalytic process. We believe this transformation will provide convenient access to previously unexplored α-trialkyl-α-tertiary amine scaffolds that should be of considerable interest to practitioners of synthetic and medicinal chemistry in academic and industrial institutions.

Poisoning effect of N-containing compounds on performance of Raney nickel in transfer hydrogenation

The effect of amines, imines and heterocycle compounds on conversion has been studied in transfer hydrogenation of camphor and 2-PrOH catalyzed by Raney nickel. Small amount (5 mol% to nickel) of N-containing compound significantly decreases catalyst activity. It has been shown that the poisoning effect mostly depends on molecular size of amines and heterocyclic compounds. For aniline and cyclohexylamine the dependence of camphor conversion on poison/nickel ratio was obtained. Additionally, benzaldehyde, cinnamaldehyde demonstrated higher reactivity compared corresponding imines under transfer hydrogenation conditions. Obtained data explain low activity of nickel-based catalysts when N-containing compounds are presented in reaction mixture.

Nucleophilic Imines and Electrophilic o-Quinone Methides, a Three-Component Assembly of Assorted 3,4-Dihydro-2 H-1,3-benzoxazines

A one-pot method for joining three separate components leading to an assortment of N-substituted 3,4-dihydro-2H-1,3-benzoxazines is described. The method involves the addition of a Grignard reagent to an o-OBoc salicylaldehyde in the presence of an imine. With a variety of components, 15 examples are presented, including the diastereoselective incorporation of chiral imines.

Ru-Catalyzed Transfer Hydrogenation of Nitriles, Aromatics, Olefins, Alkynes and Esters

This paper reports the preparation of new ruthenium(II) complexes supported by a pyrazole-phosphine ligand and their application to transfer hydrogenation of various substrates. These Ru complexes were found to be efficient catalysts for the reduction of nitriles and olefins. Heterocyclic compounds undergo transfer hydrogenation with good to moderate yields, affording examples of unusual hydrogenation of all-carbon-rings. Internal alkynes with bulky substituents show selective reduction to olefins with the unusual E–selectivity. Esters with strong electron-withdrawing groups can be reduced to the corresponding alcohols, if ethanol is used as the solvent. Possible mechanisms of hydrogenation and olefin isomerization are suggested on the basis of kinetic studies and labelling experiments.

Asymmetric Synthesis of Six-Membered Cyclic Sulfamides via Palladium-Catalyzed Alkene Carboamination Reactions

The asymmetric synthesis of six-membered cyclic sulfamides via palladium-catalyzed alkene carboamination reactions of N -homoallylsulfamides with aryl halides is described. High levels of enantioselectivity were obtained with a catalyst composed of Pd 2 dba 3 and (S)-Siphos-PE.

Optimum bifunctionality in a 2-(2-pyridyl-2-ol)-1,10-phenanthroline based ruthenium complex for transfer hydrogenation of ketones and nitriles: Impact of the number of 2-hydroxypyridine fragments

Considerable differences in reactivity and selectivity for 2-hydroxypyridine (2-HP) derived ruthenium complexes in transfer hydrogenation are described. Bifunctional Ru(ii)-(phenpy-OH) [phenpy-OH: 2-(2-pyridyl-2-ol)-1,10-phenanthroline] complex (2) exhibited excellent catalytic activity in transfer hydrogenation (TH) of ketones and nitriles. Notably, in comparison with all the reported 2-hydroxypyridine (2-HP) derived ruthenium complexes in transfer hydrogenation, complex 2 displayed significantly higher activity. Additionally, exploiting the metal-ligand cooperativity in complex 2, chemoselective TH of ketones was achieved and sterically demanding ketones were readily reduced. An outer-sphere mechanism is proposed for this system as exogenous PPh3 has no significant effect on the rate of this reaction. This is a rare example of a highly active bifunctional Ru(ii) catalyst bearing only one 2-HP unit.

Transfer Hydrogenation of Nitriles, Olefins, and N-Heterocycles Catalyzed by an N-Heterocyclic Carbene-Supported Half-Sandwich Complex of Ruthenium

In the presence of KOBut, N-heterocyclic carbene-supported half-sandwich complex [Cp(IPr)Ru(pyr)2][PF6] (3) (IPr = 1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene) catalyzes transfer hydrogenation (TH) of nitriles, activated N-heterocycles, olefins, and conjugated olefins in isopropanol at the catalyst loading of 0.5%. The TH of nitriles leads to imines, produced as a result of coupling of the initially formed amines with acetone (produced from isopropanol), and showed good chemoselectivity. Reduction of N-heterocycles occurs for activated polycyclic substrates (e.g., quinoline) and takes place exclusively in the heterocycle. The TH also works well for linear and cyclic olefins but fails for trisubstituted substrates. However, the C = C bond of α,β-unsaturated esters, amides, and acids is easily reduced even for trisubstituted species, such as isovaleriates. Mechanistic studies suggest that the active species in these catalytic reactions is the trihydride Cp(IPr)RuH3 (5), which can catalyze these reactions in the absence of any base. Kinetic studies are consistent with a classical inner sphere hydride-based mechanism of TH.

Long-chain NHC-stabilized RuNPs as versatile catalysts for one-pot oxidation/hydrogenation reactions

The synthesis and catalytic activity of long-chain NHC-stabilized RuNPs are presented. Full characterization of these novel nanostructures including surface state studies show that the ligand influences the number and the location of Ru active sites which impacts the NP catalytic activity, especially in hydrogenation reactions. The high stability and versatility of these nanosystems make them successful catalysts for both oxidation and hydrogenation reactions that can even be performed successively in a one pot-fashion.

NITROGEN-CONTAINING SATURATED HETEROCYCLIC COMPOUND

The present invention provides a compound represented by the following formula (I) or its pharmaceutically acceptable salt: [wherein, R1 represents optionally substituted C1-4 alkyl, n shows integer of 1 to 4, R2 represents optionally substituted C1-4 alkyl or hydrogen atom, R3 represents optionally substituted C1-4 alkyl, R4a, R4b, R4c, and R4d, similarly or differently, represent optionally substituted C6-14 aryl, optionally substituted C1-4 alkyl, or hydrogen atom and the like, A represents optionally substituted C6-14 aryl or optionally substituted 5 to 11 membered heteroaryl].