85225-55-4

Upstream product

• 5405-15-2 N-benzyl-N-(4-methylphenyl)amine 
• 99-77-4 ethyl 4-nitrobenzoate 
• 100-52-7 benzaldehyde 
• 99-99-0 1-methyl-4-nitrobenzene 
• 623-10-9 N-(4-methylphenyl)hydroxylamine 
• 1137-96-8 N-(benzylidene)aniline N-oxide 

Downstream Products

• 35216-23-0 3t,5-diphenyl-2-p-tolyl-(3ar,6ac)-tetrahydro-pyrrolo[3,4-d]isoxazole-4,6-dione 
• 35216-23-0 3c,5-diphenyl-2-p-tolyl-(3ar,6ac)-tetrahydro-pyrrolo[3,4-d]isoxazole-4,6-dione 
• 35216-25-2 5-(4-methoxy-phenyl)-3t-phenyl-2-p-tolyl-(3ar,6ac)-tetrahydro-pyrrolo[3,4-d]isoxazole-4,6-dione 
• 35216-25-2 5-(4-methoxy-phenyl)-3c-phenyl-2-p-tolyl-(3ar,6ac)-tetrahydro-pyrrolo[3,4-d]isoxazole-4,6-dione 
• 52165-42-1 1,1-dimethyl-4-phenyl-3-p-tolyl-3,4-dihydro-[1,2,4,5]oxatriazino[4,5-b]phthalazine-6,11-dione 
• 52165-39-6 4'-phenyl-3'-p-tolyl-3',4'-dihydro-spiro[cyclohexane-1,1'-[1,2,4,5]oxatriazino[4,5-b]phthalazine]-6',11'-dione 
• 52165-44-3 4-phenyl-1,1-dipropyl-3-p-tolyl-3,4-dihydro-[1,2,4,5]oxatriazino[4,5-b]phthalazine-6,11-dione 
• 1260501-74-3 C₂₁H₂₁NO₅ 

Relevant academic research and scientific papers

Polyfunctionalized biaryls accessed by a one-pot nucleophilic aromatic substitution and sigmatropic rearrangement reaction cascade under mild conditions

A practical synthetic method has been developed for polyfunctionalized biaryls based on a facile one-pot nucleophilic aromatic substitution (SNAr) reaction and [5,5]- or [3,3]-sigmatropic rearrangement reaction cascade. Under mild basic conditions, N-arylhydroxylamines reacted with o-activated fluoro (het)arenes to form N,O-diarylhydroxylamine intermediates which underwent spontaneously selective [5,5]-sigmatropic rearrangement reaction to produce diverse functionalized 4-amino-4′-hydroxy-1,1′-biaryls. A sequential SNAr reaction and [3,3]-sigmatropic rearrangement took place between N-arylhydroxylamines and 2-fluoropyridine derivatives or 4-fluorobenzonitrile to afford functionalized 2-amino-2′-hydroxy-1,1′-biaryls. As invaluable and unique building blocks, the resulting biaryls were applied in the straightforward synthesis of N2,O2-coronarene, carbazole, aza- and diaza carbazole derivatives.

Gold-Catalyzed Oxidative Aminocyclizations of Propargyl Alcohols and Propargyl Amines to Form Two Distinct Azacyclic Products: Carbene Formation versus a 3,3-Sigmatropic Shift of an Initial Intermediate

Gold-catalyzed oxidations of propargyl alcohols with nitrones by using a P(tBu)2(o-biphenyl)Au+ catalyst, afforded bicyclic annulation products from the Mannich reactions of gold enolates. The same reactions of propargyl amines with nitrones by using the same gold catalyst gave distinct oxoarylation products. Our DFT calculations indicate that oxidation of propargyl alcohols with nitrones by using electron-rich gold catalysts lead only to gold carbenes, which can generate gold enolates or oxoarylation intermediates with enolate species having a barrier smaller than that of oxoarylation species.

Tandem Chiral Cu(II) Phosphate-Catalyzed Deoxygenation of Nitrones/Enantioselective Povarov Reaction with Enecarbamates

A new catalytic enantioselective tandem deoxygenation/aza-Diels-Alder reaction of nitrones with enecarbamates was serendipitously discovered in the presence of chiral copper(II) diphosphate complexes. This process affords a wide range of 4-aminotetrahydroquinolines in respectable yields under mild conditions with good to excellent ee values.

Remote sp3 C–H Amination of Alkenes with Nitroarenes

Direct installation of a functional group at remote, unfunctionalized sites in an alkyl chain is a synthetically valuable but rarely reported process. The remote relay hydroarylamination of distal and proximal olefins, and of olefin isomeric mixtures, has been achieved through NiH-catalyzed alkene isomerization and sequential reductive hydroarylamination with nitroarenes. This provides an attractive approach to the direct installation of a distal arylamino group within alkyl chains. The single-step conversion of simple olefins and nitro(hetero)arenes to value-added arylamines is a practical strategy for amine synthesis as well as the remote activation of sp3 C–H bonds. The value of this transformation is further supported by the regioconvergent arylamination of isomeric mixtures of olefins. Modern organic synthesis requires more efficient strategies, such as C–H functionalization, with which to construct complex molecules from readily available chemicals. Undirected functionalization of remote aliphatic C–H bonds is a synthetically valuable but largely unknown process. Synergistic combination of metal-catalyzed chainwalking (migration of a double bond along the hydrocarbon chain, a process involving repeated migratory insertions and β-hydride eliminations) and cross-coupling chemistry offers a general approach to the remote functionalization of easily accessed unsaturated hydrocarbon substrates. In this paper, we demonstrate that direct installation of a distal arylamino group can be achieved from two common feedstock chemicals (olefins and nitroarenes) via nickel hydride chemistry. It is anticipated that the strategy could inspire the development of other remote functionalizations with different regioselectivity as well as asymmetric transformations. Zhu and colleagues describe the remote hydroamination of alkenes with nitro(hetero)arenes through nickel-catalyzed alkene isomerization and sequential reductive relay hydroamination process. Using two common feedstock chemicals, olefins and nitroaromatics, in an operationally simple procedure, this attractive protocol provides efficient and practical access to a wide range of arylamines under mild conditions.

Synthesis and Evaluation of Novel 5-cyclohexyl-2-(4″-substitutedphenyl)-3-(2″-substitutedphenyl)4H-2,3,3a,5,6,6a-hexahydropyrrolo[3,4-d]isoxazole-4,6-dione Derivatives for Their In Vitro Antioxidant and Antibacterial Activities

1,3-Dipolar cycloaddition reactions of N-cyclohexyl maleimide (1) with azomethine N-oxide (2) have afforded novel isoxazolidine (3) in excellent yield. Their structures have been characterized from their IR,1H-NMR,13C-NMR,1H,1H-COSY, MS(ESI), and elemental analysis techniques. In vitro antibacterial activity of the synthesized compounds were investigated against a representative panel of pathogenic strains specifically two Gram-positive bacteria (Staphylococcus aureus and Streptococcus pyogenes) and two Gram-negative bacteria (Pseudomonas aeruginosa and Escherichia coli) using agar-well diffusion assay. Some of the compounds (3a, 3k, 3n, and 3o) exhibited promising antibacterial activities. All the synthesized compounds have also been screened for their antioxidant activities and were found to be significantly active.

Synthesis of Benzimidazolones via One-Pot Reaction of Hydroxylamines, Aldehydes, and Trimethylsilyl Cyanide Promoted by Diacetoxyiodobenzene

A novel and efficient PhI(OAc)2-promoted one-pot reaction of aromatic hydroxylamines, aldehydes, and TMSCN in the presence of BF3·Et2O is described. A wide variety of N-substituted benzimidazolones are obtained with satisfactory yields under mild reaction conditions. The method was proven to be efficient for the synthesis of benzimidazolone derivatives from readily available starting materials.

Chiral: N, N ′-dioxide/Co(II)-promoted asymmetric 1,3-dipolar cycloaddition of nitrones with methyleneindolinones

A chiral N,N′-dioxide/Co(BF4)2·6H2O complex catalytic system has been developed to efficiently catalyze the asymmetric 1,3-dipolar cycloaddition of nitrones with methyleneindolinones. The corresponding chiral multisubstituted spiroisoxazolidines with three contiguous quaternary-tertiary stereocenters were obtained in moderate to high yields with excellent dr and ee values (up to 97% yield, >19:1 dr and 98% ee).

Visible-light-mediated anti-regioselective nitrone 1, 3-dipolar cycloaddition reaction and synthesis of bisindolylmethanes

The development of photoredox reactions of 1, 3- dipolar cycloaddition of nitrones with alkenes is reported. It offers an efficient synthetic method to obtain isoxazolidine derivatives under mild conditions in synthetically useful yields. The nitrones are cyclized with oxidizable styrenes and aliphatic alkenes via a polar radical crossover cycloaddition reaction through photocatalytic reaction without additives. In addition, bis(indole)methanes can also be prepared through this method.

Synthesis of 2,3-Disubstituted NH Indoles via Rhodium(III)-Catalyzed C-H Activation of Arylnitrones and Coupling with Diazo Compounds

A rhodium-catalyzed intermolecular coupling between arylnitrones and diazo compounds by C-H activation/[4 + 1] annulation with a C(N2)-C(acyl) bond cleavage is reported, and 2,3-disubstituted NH indoles are directly synthesized in up to a 94% yield. A variety of functional groups are applicable to this reaction to give the corresponding products with high selectivity. Compared to other previously reported Rh(III)-catalyzed synthesis of homologous series, this method is simpler, more general, and more efficient.

Influence of the side-group at C=N bridging bond of bis-aryl Schiff bases on the wavelength of absorption maximum of ultraviolet absorption spectra

The compounds N-(benzylidene)-anilines XArCH=NArY (XBAY), N-(phenyl-ethylene)-anilines XArC(CH3)=NArY (XPEAY) and N-phenyl-α-phenylnitrones XArCH=N(O)ArY (XPNY) have bridging group CH=N, C(CH3)=N and CH=N(O) respectively, in which the C(CH3)=N has a side-group methyl CH3 at carbon end and the CH=N(O) has a side-group O atom at nitrogen end. In this work, a series of XPEAY and XPNY were synthesized, and their longest wavelength maximum λmax (nm) of ultraviolet absorption spectra were measured. Then the change regularity of the νmax (cm-1, νmax=1/λmax) of XPEAY and XPNY were investigated, and they were compared with that of XBAY (reported by ref.26). The results indicate: (1) There are no good linear relationships between the νmax of XBAYs and XPEAYs or XPNYs. (2) In case of a same set of X-Y group couples, the distribution of λmax of XPEAYs is larger than that of XPNYs. (3) The side-group CH3 makes the effect of σ(X) larger than that of σ(Y) on the νmax of XPEAYs, whereas the O atom makes the effect of σ(Y) larger than that of σ(X) on the νmax of XPNYs. (4) The cross-interaction between X and Y has important effect on the all νmax. However, the cross-interaction between CH3 and X/Y has not important effect on the νmax of XPEAY, and the cross-interaction between O and X/Y has not important effect on the νmax of XPNY. Copyright