19858-02-7

Usage

Class

Azepine derivative

Uses

Pharmaceutical industry for drug synthesis

Structure

Cyclic amide with a hexahydro-1-phenylazepine core

Properties

Versatile building block for new medications

Therapeutic applications

Central nervous system disorders, potential anti-inflammatory agent

Enzyme inhibition

Potential inhibitor for certain enzymes

Organic synthesis

Applications in the field of organic synthesis

Upstream product

• 105-60-2 caprolactam 
• 591-50-4 iodobenzene 
• 502-44-3 hexahydro-2H-oxepin-2-one 
• 62-53-3 aniline 
• 603-33-8 triphenylbismuthane 
• 108-86-1 bromobenzene 
• 98-80-6 phenylboronic acid 
• 108-95-2 phenol 
• 538-51-2 benzylidene phenylamine 
• 103-84-4 Acetanilid 
• 626-86-8 adipinic acid monoethyl ester 
• 124-04-9 Adipic acid 
• 20270-53-5 di-tert-butyl 1,6-hexanedioate 
• 22809-37-6 6-bromohexanoyl chloride 

Downstream Products

• 84447-34-7 6-(phenylamino)hexan-1-ol 
• 40832-99-3 N-phenylazepane 
• 1402844-82-9 7-(1H-benzo[d]imidazol-1-yl)-1-phenylazepan-2-one 
• 62386-20-3 1-(4-chloro-phenyl)-hexahydro-azepin-2-one 
• 280120-09-4 N-[4-bromophenyl]caprolactam 

Relevant academic research and scientific papers

Metalloporphyrin-catalysed rearrangement of oxaziridines: An efficient and regioselective synthesis of lactams using ring-enlargement of N-phenyl-spirooxaziridines

Manganese(III) tetraphenylporphyrin, Mn(tpp)Cl, is a new and specific catalyst for stereo- and regio-selective rearrangement of N-phenyl-spirooxaziridines into lactams.

Development of novel conductive copolymer based on furan with improved solubility and thermal properties

The aim of this paper is to synthesize a new conductive polymer poly(phenylazepane-2-one-furan) (Abbreviated as poly(PAF)), based on the alternation of furan and a synthesized monomer phenylazepane-2-one (PA). The reaction was carried out by cationic polymerization, using a prepared heterogeneous clay catalyst called Maghnite-H+. The structure of the polymer obtained was identified by different characterization methods such as UV-Visible spectroscopy, Fourier Transform Infra-Red spectroscopy, Differential Scanning Calorimetry and Proton/carbon Nuclear Magnetic Resonance. Thermal stability was evaluated by thermogravimetric analysis, showing that poly(PAF) is stable before 200 °C. The operating conditions were optimized at T = 25 °C and t = 4 h to obtain a yield of 90percent. The poly(PAF) obtained has a linear structure and a molecular mass Mn of 7300 g/mol, which makes it soluble in common organic solvents. The indirect band-gap was calculated by Tauc formula, its value was found 1.63 eV, showing that poly(PAF) behaves like a semiconductor. Ac electrical conductivity and dielectric properties of poly(PAF) have been investigated in detail in a wide range of frequencies at room temperature.

A new synthesis of N-phenyl lactams

The synthesis of N-phenyl lactams by phase transfer oxidation of N,N- (polymethylene) anilines with potassium permanganate is reported.

Ruthenium-Pincer-Catalyzed Hydrogenation of Lactams to Amino Alcohols

By using the commercially available ruthenium pincer complex (Ru-MACHO-BH) as a catalyst, the challenging direct hydrogenation of lactams and analogues has been successfully accomplished to deliver corresponding value-added amino alcohols in good-to-excellent yields under mild reaction conditions. Remarkably, in addition to N-protected lactams, unprotected ones could also be readily reduced in the presence of a catalytic amount of weak base or even under neutral reaction conditions, which further highlights the broad substrate scope and the protocol efficiency.

Tailored Cobalt-Catalysts for Reductive Alkylation of Anilines with Carboxylic Acids under Mild Conditions

The first cobalt-catalyzed hydrogenative N-methylation and alkylation of amines with readily available carboxylic acid feedstocks as alkylating agents and H2 as ideal reductant is described. Combination of tailor-made triphos ligands with cobalt(II) tetrafluoroborate significantly improved the efficiency, thus promoting the reaction under milder conditions. This novel protocol allows for a broad substrate scope with good functional group tolerance, even in the presence of reducible alkenes, esters, and amides.

A new route to N-aromatic heterocycles from the hydrogenation of diesters in the presence of anilines

The hydrogenation of dicarboxylic acids and their esters in the presence of anilines provides a new synthesis of heterocycles. [Ru(acac)3] and 1,1,1-tris(diphenylphosphinomethyl)ethane (triphos) gave good to excellent yields of the cyclic amines at 220 °C. When aqueous ammonia was used with dimethyl 1,6-hexadienoic acid, ?-caprolactam was obtained in good yield. A side reaction involving alkylation of the amine by methanol was suppressed by using diesters derived from longer chain and branched alcohols. Hydrogenation of optically pure diesters (dimethyl (R)-2-methylbutanedioate and dimethyl (S)-2-methylbutanedioate) with aniline afforded racemic 3-methyl-1-phenylpyrrolidine in 78% yield.

Copper(II) incorporated functionalized polystyrene catalyzed: N -arylation of amides under solvent free condition with broad substrate scope

We demonstrate here, a new polystyrene supported Cu(ii) catalyzed proficient synthetic methodology for the facile N-arylation of aromatic, aliphatic, cyclic and heterocyclic amides with aryl halides under neat conditions. The catalyst, PS-Cu(ii)-ala, was prepared through the grafting of copper metal on a polystyrene-β-alanine imine network. The catalyst shows a wide range of substrate scope and excellent functional group tolerance, and produces the desired anilides in mostly high yields. The material is thoroughly characterized by DRS-UV, FT-IR, AAS, FE-SEM, TGA analysis and energy dispersive X-ray (EDX) studies. The catalyst can be easily recovered from the reaction medium and reused without significant loss of its catalytic activity suggesting future potential of this catalyst.

Selective copper-catalyzed N-arylation of lactams with arylboronic acids under base- and ligand-free conditions

An oxidative copper-catalyzed cross-coupling of arylboronic acids with various ring-size lactams has been developed. The N-arylated lactams were obtained in moderate to excellent yields without any additional bases, ligands, or additives. This reaction shows complete selectivity for N-arylation of lactams in the presence of a hydroxyl group.

CYCLIC AMIDES AS METAP-2 INHIBITORS

Compounds of the formula (I), in which R1, R3, R5, R6, R7, R, X and Y have the meanings indicated in Claim 1, are inhibitors of methionine aminopeptidase and can be employed for the treatment of tumou

An efficient copper-catalyzed N-arylation of amides: Synthesis of N-arylacrylamides and 4-amido-N-phenylbenzamides

Copper-catalyzed intermolecular C-N bond-forming reactions between aryl iodides and amides are described using sodium ascorbate, which is both cheap and nontoxic, as the additive. A variety of functionalized amides including some practical, unique secondary amides, such as N-arylacrylamides and 4-amido-N-phenylbenzamides, which are difficult to obtain by the classical methods, are prepared. Furthermore, some tertiary amides are prepared by using copper thiophenecarboxylate.