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 
• 874-60-2 4-methyl-benzoyl chloride 
• 369-57-3 benzenediazonium tetrafluoroborate 
• 104-85-8 para-methylbenzonitrile 
• 13222-85-0 p-methylbenzoic anhydride 
• 14271-73-9 4-methylbenzoyl cyanide 
• 4837-33-6 o-nitrobenzenesulfenanilide 
• 14933-91-6 N-phenyl-benzenesulphenamide 
• 25569-87-3 benzoic-p-methylbenzoic anhydride 

Downstream Products

• 34916-13-7 N-(chloro(p-tolyl)methylene)benzenamine 
• 25110-49-0 4-methyl-N,N'-diphenyl-benzamidine 
• 20199-06-8 4-methylthiobenzanilide 
• 100990-65-6 4-methyl-N-(4-(4-methylbenzamido)phenyl)-N-phenylbenzamide 
• 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 
• 100-21-0 terephthalic acid 
• 161768-67-8 N-[(Z)-1H-1,2,3-benzotriazol-1-yl(4-methylphenyl)methylidene]aniline 
• 1069123-79-0 2-p-tolyl-1H-indole-3-carboxylic acid ethyl ester 
• 1207356-66-8 C₂₀H₂₇NOSi 
• 1253388-62-3 C₂₈H₂₁NO 
• 1256360-82-3 C₂₄H₂₁NO₃ 
• 200417-08-9 methyl 2-(4-methyl-N-phenylbenzamido)benzoate 

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.

Visible-Light-Promoted Iron-Catalyzed N-Arylation of Dioxazolones with Arylboronic Acids

A visible-light-promoted and simple iron salt-catalyzed N-arylation was achieved efficiently under external photosensitizer-free conditions. Arylboronic acids and bench-stable dioxazolones were used for this cross-coupling reaction. This reaction features high reactivity, wide substrate scope, good functional group tolerance, simple operation procedure, and mild reaction conditions. Preliminary mechanistic investigations were conducted to support a radical pathway. This method may contribute to shift the paradigm of iron-catalyzed C-N bond construction and nitrene transfer chemistry.

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.

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.

Iron-catalyzed oxidative amidation of acylhydrazines with amines

A new approach for amide bond formation via a mild and efficient Iron-catalyzed cross-coupling reaction of acylhydrazines and amines using TBHP as oxidant is described. This protocol is compatible with a wide range of amines and acylhydrazines. In addition, the synthetic application of the reaction is presented.

Metal-free transamidation of benzoylpyrrolidin-2-one and amines under aqueous conditions

N-Acyl lactam amides, such as benzoylpyrrolidin-2-one, benzoylpiperidin-2-one, and benzoylazepan-2-one reacted with amines in the presence of DTBP and TBAI to afford the transamidated products in good yields. The reactions were conducted under aqueous conditions and good functional group tolerance was achieved. Both aliphatic and aromatic primary amines displayed good activity under metal-free conditions. A radical reaction pathway is proposed.

Practical one-pot amidation of N -Alloc-, N -Boc-, and N -Cbz protected amines under mild conditions

A facile one-pot synthesis of amides from N-Alloc-, N-Boc-, and N-Cbz-protected amines has been described. The reactions involve the use of isocyanate intermediates, which are generated in situ in the presence of 2-chloropyridine and trifluoromethanesulfonyl anhydride, to react with Grignard reagents to produce the corresponding amides. Using this reaction protocol, a variety of N-Alloc-, N-Boc-, and N-Cbz-protected aliphatic amines and aryl amines were efficiently converted to amides with high yields. This method is highly effective for the synthesis of amides and offers a promising approach for facile amidation.

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.