6833-18-7

Usage

InChI:InChI=1/C14H13NO/c1-11-7-9-12(10-8-11)14(16)15-13-5-3-2-4-6-13/h2-10H,1H3,(H,15,16)

Upstream product

• 79-37-8 oxalyl dichloride 
• 60-29-7 diethyl ether 
• 2998-92-7 (Z)-phenyl(p-tolyl)methanone oxime 
• 2998-91-6 p-tolyl phenyl ketoxime 
• 21443-49-2 3,4-bis(p-methylbenzoyl)-1,2,5-oxadiazole-N-oxide 
• 62-53-3 aniline 
• 104-87-0 4-methyl-benzaldehyde 
• 14338-21-7 tri-(4-methylphenyl)aluminum 
• 103-71-9 phenyl isocyanate 
• 108-88-3 toluene 
• 874-60-2 4-methyl-benzoyl chloride 
• 369-57-3 benzenediazonium tetrafluoroborate 
• 104-85-8 para-methylbenzonitrile 
• 1900-85-2 phenyl p-methylbenzoate 

Downstream Products

• 34916-13-7 N-(chloro(p-tolyl)methylene)benzenamine 
• 25110-49-0 4-methyl-N,N'-diphenyl-benzamidine 
• 5866-76-2 (4-Methyl-benzoyl)-phenyl-carbamic acid isopropyl ester 
• 40686-26-8 4-Methyl-N,N-diphenylbenzamide 
• 1027895-70-0 2-[Hydroxy-(3-methoxy-phenyl)-methyl]-4-methyl-N-phenyl-benzamide 
• 329969-90-6 [1-Benzotriazol-1-yl-1-p-tolyl-meth-(E)-ylidene]-phenyl-amine 
• 34916-13-7 N-Phenyl-p-toluol-carboximidsaeure-chlorid 
• 93-98-1 N-phenyl benzoyl amide 
• 5436-83-9 N-benzyl-4-methylbenzamide 
• 294644-43-2 N¹-{[(methyl)(phenyl)amino](selenocarbonyl)}-4-methyl-N²-phenylbenzimidamide 
• 294644-59-0 ethyl 4-(4-methylphenyl)-2-(morpholin-4-yl)-1,3-selenazole-5-carboxylate 
• 294644-40-9 4-methyl-N²-[(morpholin-4-yl)(selenocarbonyl)]-N¹-phenylbenzimidamide 

Relevant academic research and scientific papers

Water-Soluble Non-Classical Benzene Mimetics

A new generation of saturated benzene mimetics, 2-oxabicyclo[2.1.1]hexanes, was developed. These compounds were designed as analogues of bicyclo[1.1.1]pentane with an improved water solubility. Crystallographic analysis of 2-oxabicyclo[2.1.1]hexanes revea

Amide Bond Formation via the Rearrangement of Nitrile Imines Derived from N-2-Nitrophenyl Hydrazonyl Bromides

We report how the rearrangement of highly reactive nitrile imines derived from N-2-nitrophenyl hydrazonyl bromides can be harnessed for the facile construction of amide bonds. This amidation reaction was found to be widely applicable to the synthesis of primary, secondary, and tertiary amides and was used as the key step in the synthesis of the lipid-lowering agent bezafibrate. The orthogonality and functional group tolerance of this approach was exemplified by the N-acylation of unprotected amino acids.

Visible-Light Carbon Nitride-Catalyzed Aerobic Cyclization of Thiobenzanilides under Ambient Air Conditions

A metal-free heterogeneous photocatalysis has been developed for the synthesis of benzothiazoles via intramolecular C-H functionalization/C-S bond formation of thiobenzanilides by inexpensive graphitic carbon nitride (g-C3N4) under visible-light irradiation. This reaction provides access to a broad range of 2-substituted benzothiazoles in high yields under an air atmosphere at room temperature without addition of a strong base or organic oxidizing reagents. In addition, the catalyst was found to be stable and reusable after five reaction cycles.

Fe-mediated synthesis of: N -aryl amides from nitroarenes and acyl chlorides

Amides are prevalent in nature and valuable functional compounds in agrochemical, pharmaceutical, and materials industries. In this work, we developed a selective and mild method for the synthesis of N-aryl amides. Starting from commercially available nitroarenes and acyl halides, N-aryl amides with good yields can be obtained in water. Especially in the process of transformation, Fe dust is the only reductant and additive, and the reaction can be easily performed on a large scale.

Chromium-catalyzed ligand-free amidation of esters with anilines

Amides are important structural motifs in pharmaceutical and agrochemical chemistry because of the intriguing biological active properties. We report here the amidation of commercially available esters with anilines that was promoted by low-cost and air-stable chromium(III) pre-catalyst combined with magnesium, providing access to amides. This reaction occurs without the use of external ligands in a simple operation. Mechanistic studies indicate that a reactive aminated Cr species responsible for the amidation can be considered, which may be formed by reaction of low-valent Cr with aniline followed by reduction with hydrogen evolution.

Selective hydrogenation dehalogenation method of ortho-halogenated acylaniline

The invention discloses a selective hydrogenation dehalogenation method of copper-catalyzed ortho-halogenated acylaniline. The method comprises the following steps: by using ortho-halogenated acylaniline as a starting raw material and copper acetylacetonate/vasicine as a catalyst, adding an organic alkali, reacting in an alcoholic solution at 80-100 DEG C for 12 hours, and regioselectively catalytically hydrogenating ortho-bromine and iodine atoms. The preparation method has the characteristics of simplicity and convenience in operation, wide substrate application range, low cost, high regioselectivity and the like, and has practicability.

Exploration of Cu-catalyzed regioselective hydrodehalogenation of o-haloanilides using EtOH as hydrogen source

In present work, we have explored a Cu(acac)2/vasicine-catalyzed regioselective hydrodehalogenation methodology of o-haloanilides using EtOH as hydrogen source and solvent. The catalytic system could selectively dehalogenate 2-Br and 2-I, and features regioselective, efficient and functional group tolerance.

CuO-decorated magnetite-reduced graphene oxide: a robust and promising heterogeneous catalyst for the oxidative amidation of methylarenes in waterviabenzylic sp3C-H activation

A magnetite-reduced graphene oxide-supported CuO nanocomposite (rGO/Fe3O4-CuO) was preparedviaa facile chemical method and characterized by Fourier-transform infrared spectroscopy (FTIR), X-ray diffraction (XRD), UV-vis spectroscopy, scanning electron microscopy (SEM), transmission electron microscopy (TEM), energy dispersive spectroscopy (EDS), Brunauer-Emmett-Teller (BET) analysis, vibrating-sample magnetometry (VSM), and thermogravimetric (TG) analysis. The catalytic activity of the rGO/Fe3O4-CuO nanocomposite was probed in the direct oxidative amidation reaction of methylarenes with free amines. Various aromatic and aliphatic amides were prepared efficiently at room temperature from cheap raw chemicals usingtert-butyl hydroperoxide (TBHP) as a “green” oxidant and low-toxicity TBAI in water. This method combines the oxidation of methylarenes and amide bond formation into a single operation. Moreover, the synthesized nanocomposites can be separated from the reaction mixtures using an external magnet and reused in six consecutive runs without a noticeable decrease in the catalytic activity.

Regioselective Synthesis of 2° Amides Using Visible-Light-Induced Photoredox-Catalyzed Nonaqueous Oxidative C-N Cleavage of N, N-Dibenzylanilines

A visible-light-driven photoredox-catalyzed nonaqueous oxidative C-N cleavage of N,N-dibenzylanilines to 2° amides is reported. Further, we have applied this protocol on 2-(dibenzylamino)benzamide to afford quinazolinones with (NH4)2S2O8 as an additive. Mechanistic studies imply that the reaction might undergo in situ generation of α-amino radical to imine by C-N bond cleavage followed by the addition of superoxide ion to form amides.

Palladium-Catalyzed Desulfurative Hiyama Coupling of Thioureas to Achieve Amides via Selective C-N Bond Cleavage

Palladium-catalyzed Hiyama coupling of active thioureas via selective C-N bond cleavage is reported. Notably, the new approach employed active thioureas as coupling partners in the presence of arylsilanes to give amides in good yield. Further, this strategy, which utilized CuF 2as a key oxidant and activator, afforded various amide products under mild conditions and an easy to handle procedure without extra base.