74083-63-9

Upstream product

• 591-31-1 3-methoxy-benzaldehyde 
• 100-46-9 benzylamine 
• 5071-96-5 3-METHOXYBENZYLAMINE 
• 6971-51-3 3-methoxybenzyl alcohol 
• 1527-89-5 3-methoxybenzonitrile 
• 115397-88-1 (3-methoxy-benzyl)-benzyliden-amine 
• 141-52-6 sodium ethanolate 

Downstream Products

• 906483-33-8 (R)-N-benzyl-2-amino-2-(3-methoxyphenyl)acetonitrile 
• 1227750-17-5 (S)-N-benzyl-2-amino-2-(3-methoxyphenyl)acetonitrile 
• 119421-25-9 N,N'-Dibenzyl-1,2-bis-(3-methoxy-phenyl)-ethane-1,2-diamine 
• 1437798-36-1 3-benzyl-8-methoxy-2-phenylquinazolin-4(3H)-one 
• 1437798-37-2 3-benzyl-6-methoxy-2-phenylquinazolin-4(3H)-one 

Relevant academic research and scientific papers

Polyoxometalate-Driven Ease Conversion of Valuable Furfural to trans- N, N-4,5-Diaminocyclopenten-2-ones

We investigated the catalytic efficacy of silicotungstic acid (H4SiW12O40) polyoxometalate (POM) toward the reaction between furfural and amines that selectively yields trans-N,N-4,5-substituted-diaminocyclopenten-2-ones (trans-DACPs). H4SiW12O40 facilita

Design, synthesis and biological evaluation of imidazole and oxazole fragments as HIV-1 integrase-LEDGF/p75 disruptors and inhibitors of microbial pathogens

We describe here the synthesis of libraries of novel 1-subtituted-5-aryl-1H-imidazole, 5-aryl-4-tosyl-4,5-dihydro-1,3-oxazole and 5-aryl-1,3-oxazole fragments via microwave (MW)-assisted cycloaddition of para-toluenesulfonylmethyl isocyanide (TosMIC) to imines and aldehydes. The compounds obtained were biologically evaluated in an AlphaScreen HIV-1 IN-LEDGF/p75 inhibition assay with six imidazole-based compounds (16c, 16f, 17c, 17f, 20a and 20d) displaying more than 50% inhibition at 10 μM, with IC50 values ranging from 7.0 to 30.4 μM. Additionally the hypothesis model developed predicts all active scaffolds except 20d to occupy similar areas as the N-heterocyclic (A) moiety and two aromatic rings (B and C) of previously identified inhibitor 5. These results indicate that the identified compounds represent a viable starting point for their use as templates in the design of next generation inhibitors targeting the HIV-1 IN and LEDGF/p75 protein-protein interaction. In addition, the in vitro antimicrobial properties of these fragments were tested by minimum inhibitory concentration (MIC) assays showing that compound 16f exhibited a MIC value of 15.6 μg/ml against S. aureus, while 17f displayed a similar MIC value against B. cereus, suggesting that these compounds could be further developed to specifically target those microbial pathogens.

Ru Nanoparticles-Loaded Covalent Organic Framework for Solvent-Free One-Pot Tandem Reactions in Air

Condensation of benzene-1,3,5-tricarbohydrazide with benzene-1,4-dicarboxaldehyde generated a new covalent organic framework, COF-ASB (1), in which the organic units are held together via hydrazone linkage to form porous frameworks. COF-ASB (1) is highly crystalline and displays good chemical and thermal stability and is permanently porous. In addition, 1 can be an ideal support to load Ru nanoparticles (Ru NPs) to generate Ru@COF-ASB (2). The obtained composite material is able to highly promote one-pot tandem synthesis of imine products from benzyl alcohols and corresponding amines under solvent-free conditions in air.

Novel transition bimetal-organic frameworks: Recyclable catalyst for the oxidative coupling of primary amines to imines at mild conditions

A novel type of transition bimetal-organic frameworks was described as a heterogeneous catalyst for the oxidative coupling of amines to imines under mild conditions, which was easily synthesized by the coordination assembly of manganese(ii) and cobalt(ii) with 1,3,5-benzenetricarboxylic acid (H3BTC) for the first time. The metal-organic framework material was characterized by scanning electron microscopy, energy dispersive spectroscopy, X-ray photoelectron spectroscopy, X-ray diffraction, thermogravimetry and N2 sorption. As an environmentally benign heterogeneous catalyst, the catalytic ability of the metal-organic framework material was then detected to be excellent for the tert-butyl hydroperoxide (TBHP) promoted direct oxidative coupling of benzylamines to imines in excellent yields (up to 100%) in methanol for 3 h. More importantly, it could be recycled up to six runs, while still maintaining its high catalytic activity.

Selective aerobic oxidation of alcohols to aldehydes, carboxylic acids, and imines catalyzed by a Ag-NHC complex

Silver NHC catalysts have been developed for the selective oxidation of alcohols to aldehydes or carboxylic acids in the presence of BnMe3NOH or KOH under dry air. The aerobic oxidation conditions are mild, and the yield is excellent. Further tandem catalysis enables the one-pot synthesis of imines in excellent yield. Only 0.1 mol % of the catalyst is required.

General, green, and scalable synthesis of imines from alcohols and amines by a mild and efficient copper-catalyzed aerobic oxidative reaction in open air at room temperature

A general, green, and scalable synthesis of the useful imines and a,b-unsaturated imines is successfully achieved by a low-loading and powerful, mild and efficient copper-catalyzed aerobic oxidative reaction of alcohols and amines in the open air at room temperature under base- and dehydrating reagent-free conditions. This practical reaction can use air as the economic and green oxidant, tolerates a wide range of substrates, can afford high yields of the target imines on a large scale, and produces water as the only by-product, and thus being the best imination method as yet using alcohols and amines directly.

Application of sequential Cu(I)/Pd(0)-catalysis to solution-phase parallel synthesis of combinatorial libraries of dihydroindeno[1,2-c]isoquinolines

Parallel solution-phase synthesis of combinatorial libraries of dihydroindenoisoquinolines employing a sequential Cu(I)/Pd(0)-catalyzed multicomponent coupling and annulation protocol was realized. The scope and limitations of the protocol with respect to the substitution pattern in the aryl ring of the indene core, as well as the N-substituent have been defined, revealing that the methodology is compatible with a wide-range of aliphatic linear, branched, and ester functionalized N-substituents. Unexpectedly, the formation of regioisomers featuring a 1,2,3-contiguous substitution pattern in the aromatic ring of the indene core was observed. Three distinct combinatorial libraries with a total of 111 of members were synthesized, and 80 highly substituted dihydroindenoisoquinolines structurally related to known medicinal agents including some consisting of mixtures of two regioisomers were made available for biological activity testing.

Asymmetric addition of trimethylsilylcyanide to N-benzylimines catalyzed by recyclable chiral dimeric V(V) salen complex

Chiral dimeric vanadium (V) salen complex (10 mol%) derived from 5,5-Methylene di-[(S,S)-{N-(3-tert-butyl salicylidine)-N′-(3′,5′-di-tert-butyl salicylidene)]-1,2-cyclohexanediamine] with vanadyl suphate followed by auto oxidation was used as efficient catalyst for enantioselective Strecker reaction of N-benzylimines with TMSCN at -30 °C. Excellent yield (92%) of α-aminonitrile and high chiral induction was achieved (ee up to 94%) in case of 2-methoxy substituted N-benzylimines in 10 h. The catalytic system worked well up to four cycles with retention of enantioselectivity.

Catalytic, asymmetric Strecker reactions catalysed by titaniumIV and vanadiumV(salen) complexes

VanadiumV(salen) complex 3 has been found to be an effective catalyst for the asymmetric addition of hydrogen cyanide (generated in situ from trimethylsilyl cyanide) to imines. The best results (up to 81% enantiomeric excess) were obtained for aromatic imines in which the nitrogen atom is protected with a benzyl group and in which the imine bond is not sterically encumbered.

Effective reductive amination of carbonyl compounds with hydrogen catalyzed by iridium complex in organic solvent and in ionic liquid

The direct reductive amination (DRA) of carbonyl compounds with amines has been achieved using homogenous iridium catalyst and gaseous hydrogen. It appeared that the cationic iridium catalyst, [Ir(cod)2]BF 4, without any other ligands was sufficient for the reaction. For the DRA of the ketone substrates, an ionic liquid, [Bmim]BF4, was found to be superior to the other organic solvent used. Especially, the counter anion of the ionic liquid has a significant influence on the selectivity, and at the same time, a high reaction temperature was found to be crucial for the excellent selectivity.