107175-80-4

Upstream product

• 77499-86-6 1-benzyl-4-phenyl-1-aza-1,3-butadiene 
• 104-54-1 3-Phenylpropenol 
• 57620-22-1 N-benzyl-2,4-dinitro-benzenesulfonamide 
• 85217-69-2 cinnamyl methyl carbonate 
• 62-53-3 aniline 
• 100-46-9 benzylamine 
• 68-12-2 N,N-dimethyl-formamide 
• 7217-71-2 1-phenyl-2-propenyl acetate 
• 103-54-8 cinnamyl acetate 
• 104-55-2 3-phenyl-propenal 
• 4407-36-7 (2E)-3-phenyl-2-propen-1-ol 
• 536-74-3 phenylacetylene 
• 511286-64-9 (+/-) 3,5-dibenzyl[1,2,3]oxathiazolidine-2,2-dioxide 
• 2687-12-9 cinnamyl chloride 

Downstream Products

• 231606-12-5 C₂₀H₂₁Cl₂NO 
• 100-61-8 N-methylaniline 

Relevant academic research and scientific papers

Cycloamidination of Aminoalkenes with Nitriles: Synthesis of Substituted 2-Imidazolines and Tetrahydropyrimidines

The first catalytic cycloamidination of aminoalkenes with nitriles has been achieved by using rare-earth complexes. This reaction is equivalent to the desired intramolecular hydroamination of alkenylamidines, and allows a new direct access to substituted 2-imidazolines and tetrahydropyrimidines in high yields under operationally simple reaction conditions. Moreover, the methodology is also efficient for synthesis of symmetric and unsymmetric bridged diimidazolines. Compared with the traditional stepwise-mediated synthetic approaches, the present method avoids the use of additives and harsh reaction conditions, and thus leads to a completely different product distribution. Mechanistic data suggest that the reaction involves the initial NH activation by lanthanide complex followed by nitrile insertion into a Ln-N bond to form an amidinate lanthanide intermediate which undergoes the cyclization.

Palladium-Catalyzed Allyl-Allyl Reductive Coupling of Allylamines or Allylic Alcohols with H2as Sole Reductant

Catalytic carbon-carbon bond formation building on reductive coupling is a powerful method for the preparation of organic compounds. The identification of environmentally benign reductants is key for establishing an efficient reductive coupling reaction. Herein an efficient strategy enabling H2 as the sole reductant for the palladium-catalyzed allyl-allyl reductive coupling reaction is described. A wide range of allylamines and allylic alcohols as well as allylic ethers proceed smoothly to deliver the C-C coupling products under 1 atm of H2. Kinetic studies suggested that the dinuclear palladium species was involved in the catalytic cycle.

A proton-responsive annulated mesoionic carbene (MIC) scaffold on IR complex for proton/hydride shuttle: An experimental and computational investigation on reductive amination of aldehyde

A Cp*Ir(III) complex (1) bearing a proton-responsive hydroxy unit on an annulated imidazo[1,2-a][1,8]naphthyridine based mesoionic carbene scaffold was synthesized by two different synthetic routes. The molecular structure of 1 revealed an anionic lactam form of the ligand. The acid?base equilibrium between the lactam-lactim tautomers on the ligand scaffold was examined by 1H NMR and UV?vis spectra. The pKa of the appendage ?OH group in the lactim form of 1 was estimated to assess the proton transfer property of the catalyst. The catalytic efficacy of 1 for reductive amination of aldehyde was evaluated by utilizing three different hydrogen sources: molecular H2iPrOH/KOtBu combination, and HCOOH/Et3N (5:2) azeotropic mixture. The HCOOH/Et3N (5:2) azeotropic mixture rotocol was found to be the best amon the three different h dro enation methods. Catalyst 1 hydrogenates imines chemoselectively over carbonyls under the reaction conditions. A range of aldehydes was reductively aminated to the corresponding secondary amines using the HCOOH/Et3N (5:2) azeotropic mixture. Further, catalyst 1 showed high efficiency for the reduction of a wide variety of N-heterocyclic imine derivatives. The lactam-lactim tautomerization of the ligand system is proposed for direct hydrogenation, whereas only the lactam form operates in the strongly basic medium (iPrOH/KOtBu). Under HCOOH/Et3N (5:2) conditions, the lactam scaffold is not protonated; rather, an outer-sphere hydride transfer from formate to the Ir is proposed, which is supported by 1H NMR and DFT calculations. Finally, ligand-promoted hydride transfer from metal-hydride to the protonated imine affords the corresponding amine. A close agreement between the experimentally estimated and computed thermodynamic/kinetic parameters gives credence to the metal-ligand cooperative mechanism for the imine hydrogenation reaction using the HCOOH/Et3N (5:2) azeotropic mixture.

Silylative Reductive Amination of α,β-Unsaturated Aldehydes: A Convenient Synthetic Route to β-Silylated Secondary Amines

Described here is a reductive amination/hydrosilylation cascade of α,β-unsaturated aldehydes mediated by a Lewis acidic borane catalyst. The present reaction system provides an one-pot synthetic route towards β-silylated secondary amines that have not been accessible by other previous catalysis. Comparative 1H NMR studies on the silylative reduction of enimines revealed that steric bulkiness of primary amine reactants strongly affects both catalytic efficiency and regioselectivity. This strategy was applicable to a broad range of substrates and amenable to one-pot gram-scale synthesis. Moreover, a diastereoselective introduction of the β-silyl group was also found to be feasible (d.r. up to 71:29).

A Simple, Broad-Scope Nickel(0) Precatalyst System for the Direct Amination of Allyl Alcohols

The preparation of allylic amines is traditionally accomplished by reactions of amines with reactive electrophiles, such as allylic halides, sulfonates, or oxyphosphonium species; such methods involve hazardous reagents, generate stoichiometric waste streams, and often suffer from side reactions (such as overalkylation). We report here the first broad-scope nickel-catalysed direct amination of allyl alcohols: An inexpensive NiII/Zn couple enables the allylation of primary, secondary, and electron-deficient amines without the need for glove-box techniques. Under mild conditions, primary and secondary aliphatic amines react smoothly with a range of allyl alcohols, giving secondary and tertiary amines efficiently. This “totally catalytic” method can also be applied to electron-deficient nitrogen nucleophiles; the practicality of the process was demonstrated in an efficient, gram-scale preparation of the calcium antagonist drug substance flunarizine (Sibelium).

Synthesis of N?H Bearing Imidazolidinones and Dihydroimidazolones Using Aza-Heck Cyclizations

The synthesis of unsaturated, unprotected imidazolidinones via an aza-Heck reaction is described. This palladium-catalyzed process allows for the cyclization of N-phenoxy ureas onto pendant alkenes. The reaction has broad functional group tolerance, can b

Containing dinaphthyl [1, 2-b; 5, 6-b '] chiral phosphine nitrogen skeleton and cyclooctatetraene π-ene propyl iridium complex, synthesis method and application

The invention provides an optically pure pi-allyl iridium complex containing dinaphthyl [1,2-b;5,6-b'] cyclooctatetraene and a chiral phosphine nitrogen framework as well as a synthesizing method and application of the complex in an asymmetric allyl subst

Immobilized catalysts for iridium-catalyzed allylic amination: Rate enhancement by immobilization

The first immobilized catalyst for Ir-catalyzed asymmetric allylic aminations is described. The catalyst is a cationic (π-allyl)Ir complex bound by cation exchange to an anionic silica gel support. Preparation of the catalyst is facile, and the supported

Synthesis, characterization and in vitro antibacterial activity of cinnamyl amine derivatives

A series of cinnamyl amine derivatives have been synthesized and characterized by their MS, 1H and 13C NMR spectral data. Antibacterial activity has been evaluated against three Grampositive (Bacillus subtilis MTCC 121, Staphylococcus aureus MTCC 96 and Staphylococcus epidermidis MTCC 435) and two Gram-negative (Escherichia coli MTCC 723 and Pseudomonas aeruginosa MTCC 741) bacteria. The Schiff base derivatives benzyl-(3- phenylallylidene)amine 3, phenyl-(3-phenylallylidene)amine 4 and amine derivatives 2-[benzyl-(3-phenylallyl)-amino]-1-(4-methoxyphenyl)ethanone 8c and 1-(4-bromophenyl)-2-[phenyl-(3-phenylallyl)-amino]ethanone 9c showed remarkable antibacterial activity against B. subtilis, S. aureus and S. epidermidis bacterial strains even at low concentration and are close to the standard antibiotic streptomycin (MIC 3.3-7.0 μg mL-1). Furthermore, methoxy substitution at phenacyl nucleus increased the antibacterial activity as compared to the methyl and bromo substituents under identical conditions.

N-Allylation of amines with allyl acetates using chitosan-immobilized palladium

A simple procedure for N-allylation of amines with allyl acetates has been developed using a biodegradable and easily recyclable heterogeneous chitosan-supported palladium catalyst. The general methodology, applicable to a wide range of substrates, has sustainable features that include a ligand-free reaction with simple workup, recycling and reusability of the catalyst.