13548-24-8

Upstream product

• 100-52-7 benzaldehyde 
• 6315-89-5 3,4-dimethoxyaniline 
• 100-51-6 benzyl alcohol 

Downstream Products

• 1259379-44-6 C₁₈H₂₃NO₃ 
• 1259379-69-5 C₁₈H₂₁NO₂ 
• 1419351-72-6 benzyl ((E)-2-((2S,4R)-6,7-dimethoxy-2-phenyl-1,2,3,4-tetrahydroquinolin-4-yl)vinyl)carbamate 
• 1419351-73-7 C₂₇H₂₈N₂O₄ 
• 1140966-35-3 (6,7-dimethoxy-2-phenyl-1,2,3,4-tetrahydro-quinolin-4-yl)-carbamic acid benzyl ester 
• 619319-76-5 N-benzyl-3,4-dimethoxychloroacetanilide 
• 39217-14-6 N-(3,4-dimethoxyphenyl)-N-benzylamine 
• 857584-15-7 9,10-dimethoxy-12-phenyl-7,12-dihydro-benz[a]acridine 

Relevant academic research and scientific papers

Copper-catalyzed highly efficient aerobic oxidative synthesis of imines from alcohols and amines

A highly efficient and green tandem imine synthesis from alcohol and amine with molecular oxygen as oxidant was achieved by using a remarkable low catalyst-loading, with a commercially available and environmentally benign copper catalyst.

Azetidinimines as a novel series of non-covalent broad-spectrum inhibitors of β-lactamases with submicromolar activities against carbapenemases KPC-2 (class A), NDM-1 (class B) and OXA-48 (class D)

The occurrence of resistances in Gram negative bacteria is steadily increasing to reach extremely worrying levels and one of the main causes of resistance is the massive spread of very efficient β-lactamases which render most β-lactam antibiotics useless. Herein, we report the development of a series of imino-analogues of β-lactams (namely azetidinimines) as efficient non-covalent inhibitors of β-lactamases. Despite the structural and mechanistic differences between serine-β-lactamases KPC-2 and OXA-48 and metallo-β-lactamase NDM-1, all three enzymes can be inhibited at a submicromolar level by compound 7dfm, which can also repotentiate imipenem against a resistant strain of Escherichia coli expressing NDM-1. We show that 7dfm can efficiently inhibit not only the three main clinically-relevant carbapenemases of Ambler classes A (KPC-2), B (NDM-1) and D (OXA-48) with Ki's below 0.3 μM, but also the cephalosporinase CMY-2 (class C, 86% inhibition at 10 μM). Our results pave the way for the development of a new structurally original family of non-covalent broad-spectrum inhibitors of β-lactamases.

Metal-Free Ring Opening Cyclization of Cyclopropane Carbaldehydes and N-Benzyl Anilines: An Eco-Friendly Access to Functionalized Benzo[b]azepine Derivatives

Herein, we report a p-toluenesulfonic acid (PTSA) initiated mild and user-friendly ring opening/domino ring opening cyclization reaction (depends on substituent present in N-benzyl aniline) of cyclopropane carbaldehyde and N-benzyl aniline towards the formation of substituted 4-amino butanal/2,3-dihydro-1H-benzo[b]azepine. The product dihydro-1H-benzo[b]azepine was also converted into the corresponding tetrahydro-1H-benzo[b]azepine. (Figure presented.).

Synthesis of optically active 1,2,3-trisubstituted azetidines employing an organocatalytic approach with L-proline

A concise organocatalytic approach towards optically active 1,2,3-trisubstituted azetidines, including a study of the scope and limitations of the synthetic sequence, is reported. The synthesis comprises the one-pot L-proline promoted three-component reac

Synthesis and antifungal activity of N-aryl-N-benzylamines and of their homoallyl analogues

Ten N-aryl-N-benzylamines were synthesized and evaluated for their antifungal activity, which was compared with their homoallylamine analogues that possessed an allyl group in the carbon next to the nitrogen atom. Results indicated that the absence of the allyl group caused an enhancement of the antifungal activity which could be correlated with the flexibility of the alkyl chain between both aromatic groups. DFT calculations supported these differences in activity. ARKAT-USA, Inc.

Organocatalytic asymmetric Povarov reactions with 2- and 3-vinylindoles

The asymmetric Povarov reaction of N-arylimines with 2- and 3-vinylindoles has been developed using a chiral phosphoric acid ((S)-TRIP) as catalyst. The peculiar reactivity of vinylindoles allowed also the disclosure of a Povarov Friedel-Crafts sequence,

π-π Stacking versus steric effects in stereoselectivity control: Highly diastereoselective synthesis of syn-1,2-diarpropylamines

N-Arylarylideneamines react with sulfinylbenzyl carbanions derived from 2-(p-tolylsulfinyl)toluenes (S)-1 and (S)-2, affording epimeric mixtures at C1 of 1,2-diarylethyl- and 1,2-diarylpropylamine derivatives. The sulfinyl group completely controls the configuration at C2 in the reactions of (S)-2. The configuration at Cl depends on the electron density of the ring adjacent to the iminic carbon atom which is modulated by π-π stacking interactions with the ring joined to the carbanionic centre. The stereoselectivity was controlled by modifying the acceptor character of the arylideneamine ring with appropriate substituents, the formation of the highly selective (R) configuration at C1 being made possible by electron-donating groups. N-(2,4,6-Trimethoxyphenyl) arylideneamines have been shown to be suitable starting materials for the preparation of (R)-1,2-diarylethyl- and (1R,2S)-1,2-diarylpropylamines (syn epimers) in a highly stereoselective manner.

Highly stereoselective reactions of γ-sulfinyl carbanions with achiral imines

Lithium 2-p-tolylsulfinylbenzyl carbanions react with different N-substituted imines affording 1,2-diaryl ethyl (and propyl) amines with a high stereoselectivity control at both benzyllic (only dependent of the sulfur configuration) and iminic carbons. The anti:syn ratio, ranging between >96:98, dependent on the electronic density at nitrogen. Copyright Taylor & Francis Inc.

In vitro antifungal activity of new series of homoallylamines and related compounds with inhibitory properties of the synthesis of fungal cell wall polymers

The synthesis, in vitro antifungal evaluation and SAR studies of 101 compounds of the 4-aryl-, 4-alkyl-, 4-pyridyl or -quinolinyl-4-N-arylamino-1-butenes series and related compounds, are reported here. Active structures showed to inhibit (1,3)-β-D-glucan and mainly chitin synthases, enzymes that catalyze the synthesis of the major fungal cell wall polymers.

Synthesis of substituted oxindoles from α-chloroacetanilides via palladium-catalyzed C - H functionalization

A novel method for the synthesis of oxindoles is described. In the presence of catalytic palladium acetate and 2-(di-tert-butylphosphino)biphenyl, α-chloroacetanilides are converted to oxindoles in good to excellent yields with high functional group compatibility using triethylamine as a stoichiometric base. The cyclization is highly regioselective, obviating the need for prefunctionalized arenes. Plausible mechanistic pathways for the reaction are discussed. Copyright