42974-61-8

Upstream product

• 59507-51-6 4-(N-cyclohexyl-amino-methyl)-nitrobenzene 
• 99-99-0 1-methyl-4-nitrobenzene 
• 108-91-8 cyclohexylamine 
• 619-73-8 4-nitrobenzyl chloride 
• 7506-46-9 N-cyclohexyl-4-nitrobenzamide 
• 555-16-8 4-nitrobenzaldehdye 

Downstream Products

• 56251-36-6 N-Cyclohexyl-p-nitrophenyl-α-chloracetamid 
• 59507-51-6 4-(N-cyclohexyl-amino-methyl)-nitrobenzene 
• 858661-93-5 (E)-2-cyclohexyl-3-p-nitrophenyloxaziridine 

Relevant academic research and scientific papers

Activated Self-Resolution and Error-Correction in Catalytic Reaction Networks**

Understanding the emergence of function in complex reaction networks is a primary goal of systems chemistry and origin-of-life studies. Especially challenging is to create systems that simultaneously exhibit several emergent functions that can be independently tuned. In this work, a multifunctional complex reaction network of nucleophilic small molecule catalysts for the Morita-Baylis-Hillman (MBH) reaction is demonstrated. The dynamic system exhibited triggered self-resolution, preferentially amplifying a specific catalyst/product set out of a many potential alternatives. By utilizing selective reversibility of the products of the reaction set, systemic thermodynamically driven error-correction could also be introduced. To achieve this, a dynamic covalent MBH reaction based on adducts with internal H-transfer capabilities was developed. By careful tuning of the substituents, rate accelerations of retro-MBH reactions of up to four orders of magnitude could be obtained. This study thus demonstrates how efficient self-sorting of catalytic systems can be achieved through an interplay of several complex emergent functionalities.

Vanadium-and chromium-catalyzed dehydrogenative synthesis of imines from alcohols and amines

Vanadium(IV) tetraphenylporphyrin dichloride and chromium(III) tetraphenylporphyrin chloride have been developed as catalysts for the acceptorless dehydrogenation of alcohols. The catalysts have been applied to the direct synthesis of imines in overall good yields from a variety of alcohols and amines. The transformations are proposed to proceed by metal?ligand bifunctional pathways with an outer-sphere transfer of two hydrogen atoms from the alcohol to the metal porphyrin complexes. The results show that vanadium and chromium catalysts can also be employed for the dehydrogenation of alcohols with the release of hydrogen gas, and they may represent valuable alternatives to other catalysts based on Earth-abundant metals.

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.

Synthesis and molecular docking studies of imines as α-glucosidase and α-amylase inhibitors

Imine functionality is found in many compounds with important biological activity. Thus, the development of novel synthetic approaches for imines is important. In this work, it is propose an easy, eco-friendly and straightforward synthesis pathway of aryl imines under microwave irradiation catalyzed by Alumina-sulfuric acid. In addition, the in vitro enzymatic inhibition, antioxidant activity and molecular docking studies were performed. The aryl imines were isolated with yields in the range of 37–94%. All aryl imines synthesized were evaluated for in vitro inhibitory potential against α-glucosidase and α-amylase enzymes and the results exhibited that the most of the compounds displayed inhibitory activity against both enzymes. The (E)-1-(4-nitrophenyl)-N-(pyridin-2-yl)methanimine (3d) was 1.15-fold more active than acarbose against α-amylase whilst the (E)-1-phenyl-N-(pyridin-2-yl)methanimine (3c) displayed similar activity that acarbose against α-glucosidase. The molecular docking studies in α-glucosidase and α-amylase reveal that aryl imines mainly establish an H-bond with the R2-subtituent and hydrophobic interactions with the R1-subtituent. The docking analysis reveals these synthetic aryl imines 3d-i interact in same active site than acarbose drug in both enzymes.

Development and mechanistic investigation of the manganese(iii) salen-catalyzed dehydrogenation of alcohols

The first example of a manganese(iii) catalyst for the acceptorless dehydrogenation of alcohols is presented. N,N′-Bis(salicylidene)-1,2-cyclohexanediaminomanganese(iii) chloride (2) has been shown to catalyze the direct synthesis of imines from a variety of alcohols and amines with the liberation of hydrogen gas. The mechanism has been investigated experimentally with labelled substrates and theoretically with DFT calculations. The results indicate a metal-ligand bifunctional pathway in which both imine groups in the salen ligand are first reduced to form a manganese(iii) amido complex as the catalytically active species. Dehydrogenation of the alcohol then takes place by a stepwise outer-sphere hydrogen transfer generating a manganese(iii) salan hydride from which hydrogen gas is released.

Manganese(III) Porphyrin-Catalyzed Dehydrogenation of Alcohols to form Imines, Tertiary Amines and Quinolines

Manganese(III) porphyrin chloride complexes have been developed for the first time as catalysts for the acceptorless dehydrogenative coupling of alcohols and amines. The reaction has been applied to the direct synthesis of imines, tertiary amines and quinolines where only hydrogen gas and/or water are formed as the by-product(s). The mechanism is believed to involve the formation of a manganese(III) alkoxide complex which degrades into the aldehyde and a manganese(III) hydride species. The latter reacts with the alcohol to form hydrogen gas and thereby regenerates the alkoxide complex.

Cobalt-Catalyzed Dehydrogenative Coupling of Amines into Imines

Primary amines have been subjected to an acceptorless dehydrogenative homo- and heterocoupling into imines with a cobalt catalyst. The catalytically active species are composed of cobalt nanoparticles, which are generated in situ by heating Co2(CO)8 in the presence of trioctylphosphine oxide as a surfactant. The nanoparticles have been characterized by transmission electron microscopy where the image showed spherical and small particles with a narrow size distribution. The catalyst can be recovered and used again with essentially no effect on the yield. The catalyst can also be used for the dehydrogenative coupling of alcohols and amines into imines.

In Situ Generated Cobalt Catalyst for the Dehydrogenative Coupling of Alcohols and Amines into Imines

An in situ formed cobalt catalyst is developed from cobalt(II)bromide, bis[2-(diisopropylphosphino)-4-methylphenyl]amine and zinc metal. The catalyst mediates the acceptorless dehydrogenative coupling of alcohols and amines into imines with the release of hydrogen gas and the transformation is applied to the synthesis of a variety of imines from different alcohols and amines. The mechanism is investigated with labelled substrates and based on the results a cobalt(I) PNP complex is believed to be the catalytically active species which abstracts hydrogen gas from the alcohol through a metal ligand bifunctional pathway.

Molybdenum-Catalyzed Dehydrogenative Synthesis of Imines from Alcohols and Amines

A molybdenum N-heterocyclic carbene catalyst has been developed for the synthesis of imines from primary alcohols and amines with the liberation of dihydrogen. The catalyst is generated in situ from molybdenum hexacarbonyl, 1,3-dicyclohexylimidazolium chloride and potassium tert-butoxide and is further stabilized by the phosphine ligand dppe. Imines are formed in moderate to good isolated yields and a variety of alcohols and amines can be employed in the reaction including anilines. The transformation constitutes the first example of a homogeneous molybdenum-catalyzed acceptorless dehydrogenative coupling with alcohols and is believed to proceed by formation of a cis-coordinated molybdenum bis-N-heterocyclic carbene complex, which performs an oxidative addition to the alcohol, β-hydride elimination and reductive elimination of dihydrogen.

Aerobic oxidative coupling of alcohols and amines towards imine formation by a dicopper(I,I) catalyst

A dicopper(I,I) complex [Cu2(L1) (Cl)2] (1), bearing a Cu2Cl2 core spanned by a naphthyridine–diimine ligand is synthesized by the treatment of CuCl with 2,7–bis(N–mesitylmethylimino)–1,8–naphthyridine (L1). The catalytic efficacy of 1 is assessed for aerobic oxidative synthesis of imines from alcohols and amines. The title complex is found to be an excellent catalyst for a wide variety of alcohols and amines. Kinetic experiments revealed the involvement of both copper ions in the aerobic oxidation process. The general utility of naphthyridine based ligands to favour a possible bimetallic pathway for a catalytic reaction is demonstrated here.