- α-Aryl-N-aryl nitrones: Synthesis and screening of a new scaffold for cellular protection against an oxidative toxic stimulus
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Nitrone-containing compounds are commonly employed as spin traps of free radical species in chemical and biological studies. Some molecules as α-phenyl-N-t-butyl nitrone (PBN) and its derivatives have been tested as potential drugs to treat oxidative stress related diseases, as Alzheimer and stroke for example. In this work we report the design and the synthesis of α-aryl-N-aryl nitrones and their cytoprotection profile on human neuroblastoma cells (SH-SY5Y) under induced oxidative stress. All the nine synthesized nitrones showed a significant response at low micromolar concentration. The selected compound 8 (α-phenyl-N-phenyl nitrone) increased the reduced glutathione (GSH) levels by 65% and lowered the necrotic cell death from 25.8% to 3.8%. Based on our data, the designed highly conjugated nitrone double-bond skeleton can be considered as a good scaffold for further studies regarding oxidative stress-related diseases.
- Matias,Biazolla,Cerchiaro,Keppler
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- DFT study of 1,3-dipolar cycloadditions of C,N-disubstituted aldonitrones to chalcones evidenced by NMR and X-ray analysis
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A DFT/B3LYP/6-31G*study was carried out to predict the regio- and stereoselectivities of 1,3-dipolar cycloadditions of C,N-disubstituted aldonitrones to chalcones in terms of FMO theory, DFT-based reactivity indices, and activation energy calculations. Th
- Acharjee, Nivedita,Banerji, Avijit,Prange, Thierry
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- Gold Catalysts Can Generate Nitrone Intermediates from a Nitrosoarene/Alkene Mixture, Enabling Two Distinct Catalytic Reactions: A Nitroso-Activated Cycloheptatriene/Benzylidene Rearrangement
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Gold-catalyzed reactions of cycloheptatrienes with nitrosoarenes yield nitrone derivatives efficiently. This reaction sequence enables us to develop gold-catalyzed aerobic oxidations of cycloheptatrienes to afford benzaldehyde derivatives using CuCl and nitrosoarenes as co-catalysts (10-30 mol %). Our density functional theory calculations support a novel nitroso-activated rearrangement, tropylium → benzylidene. With the same nitrosoarenes, we developed their gold-catalyzed [2 + 2 + 1]-annulations between nitrosobenzene and two enol ethers to yield 5-alkoxyisoxazolidines using 1,4-cyclohexadienes as hydrogen donors.
- Cheng, Mu-Jeng,Kardile, Rahul Dadabhau,Kuo, Tung-Chun,Liu, Rai-Shung,More, Sayaji Arjun
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supporting information
p. 5506 - 5511
(2021/07/31)
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- Optimized aqueous Kinugasa reactions for bioorthogonal chemistry applications
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Kinugasa reactions hold potential for bioorthogonal chemistry in that the reagents can be biocompatible. Unlike other bioorthogonal reaction products, β-lactams are potentially reactive, which can be useful for synthesizing new biomaterials. A limiting factor for applications consists of slow reaction rates. Herein, we report an optimized aqueous copper(i)-catalyzed alkyne-nitrone cycloaddition involving rearrangement (CuANCR) with rate accelerations made possible by the use of surfactant micelles. We have investigated the factors that accelerate the aqueous CuANCR reaction and demonstrate enhanced modification of a model membrane-associated peptide. We discovered that lipids/surfactants and alkyne structure have a significant impact on the reaction rate, with biological lipids and electron-poor alkynes showing greater reactivity. These new findings have implications for the use of CuANCR for modifying integral membrane proteins as well as live cell labelling and other bioorthogonal applications.
- Bilodeau, Didier A.,Margison, Kaitlyn D.,Ahmed, Noreen,Strmiskova, Miroslava,Sherratt, Allison R.,Pezacki, John Paul
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supporting information
p. 1988 - 1991
(2020/02/25)
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- 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
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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.
- Chao, Tzu-Hsuan,Chen, Mu-Jeng,Liu, Rai-Shung,Raj, Antony Sekar Kulandai,Sasane, Amit Vijay
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supporting information
p. 16932 - 16938
(2020/11/30)
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- Nitrone synthesis via pair electrochemical coupling of Nitro-Compounds with Benzyl Alcohol Derivatives
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Here we report a paired electrochemical coupling of readily accessible nitro-compounds with benzyl alcohols to yield nitrone derivatives. In this work, electrochemical behavior of nitrobenzene and benzyl alcohol derivatives was studied by cyclic voltammetry and controlled potential coulommetry. Electrochemical reactions have been performed in aqueous/ethanol (or acetonitrile) solutions by employing common graphite electrodes and a simple controlled current protocol which can make this strategy more appealing than other conventional pathways.
- Salehzadeh, Hamid,Mashhadizadeh, Mohammad Hossein
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p. 9307 - 9312
(2019/07/08)
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- Synthesis of Exclusively 4-Substituted β-Lactams through the Kinugasa Reaction Utilizing Calcium Carbide
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A new Kinugasa reaction protocol has been elaborated for the one-pot synthesis of 4-substituted β-lactams utilizing calcium carbide and nitrone derivatives. Calcium carbide is thereby activated by TBAF·3H2O in the presence of CuCl/NMI. The ease of synthesis and use of inexpensive chemicals provides rapid access of practical quantities of β-lactams exclusively substituted at position 4.
- Hosseini, Abolfazl,Schreiner, Peter R.
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supporting information
p. 3746 - 3749
(2019/05/24)
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- Catalytic Diastereo- and Enantioselective Synthesis of 2-Imidazolinones
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Chiral cyclic ureas (2-imidazolinones) were prepared by the reaction of nitrones and isocyanoacetate esters using a multicatalytic system that combines a bifunctional Br?nsted base-squaramide organocatalyst and Ag+ as a Lewis acid. The reaction could be achieved with a range of nitrones derived from aryl- and cycloalkylaldehydes with moderate diastereo- and good enantioselectivity. A plausible mechanism involving an initial formal [3 + 3] cycloaddition of the nitrone and isocyanoacetate ester, followed by rearrangement to an aminoisocyanate and cyclization to the imidazolinone, is proposed.
- Martínez-Pardo, Pablo,Blay, Gonzalo,Escrivá-Palomo, Alba,Sanz-Marco, Amparo,Vila, Carlos,Pedro, José R.
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supporting information
p. 4063 - 4066
(2019/06/17)
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- Catalytic Transformations of Alkynes into either α-Alkoxy or α-Aryl Enolates: Mannich Reactions by Cooperative Catalysis and Evidence for Nucleophile-Directed Chemoselectivity
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The catalytic formation of gold enolates from alkynes, nitrones, and nucleophiles is described, and their Mannich reactions result in nucleophile-directed chemoselectivity through cooperative catalysis. For 1-alkyn-4-ols and 2-ethynylphenols, their gold-catalyzed nitrone oxidations afforded N-containing dihydrofuran-3(2H)-ones with syn selectivity. The mechanism involves the Mannich reactions of gold enolates with imines through an O-H-N hydrogen-bonding motif. For aryloxyethynes, their gold enolates react selectively with nitrones to deliver 3-alkylidenebenzofuran-2-ones, as controlled by a C-H-O hydrogen-bonding motif.
- Sahani, Rajkumar Lalji,Patil, Manoj D.,Wagh, Sachin Bhausaheb,Liu, Rai-Shung
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supporting information
p. 14878 - 14882
(2018/10/15)
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- 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
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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.
- Kaur, Manpreet,Kaur, Anjandeep,Singh, Baldev,Singh, Baljit
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- Preparation method of 2-amino-5-halogen phenol compounds
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The invention relates to a preparation method of 2-amino-5-halogen phenol compounds. The compounds are very important intermediates in fine chemistry. Due to the ortho-position special relation of a hydroxyl group in an amino group, the compounds are important raw materials for preparing heterocyclic compounds such as the benzoxazolone compound and the benzothiazolone compound which are intermediates with the important value in medical drugs. The 2-amino-5-halogen phenol compounds can serve as anti-cancer drugs such as hydroxamic acid anti-cancer drugs and intermediates of dye and have wide application in chemical engineering, soft matter, materials and the like. According to the method, nitrone is taken as a raw material and easily prepared from a halogen nitrobenzene compound; raw materials of the halogen nitrobenzene compound are low in cost and wide in source.
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Paragraph 0024; 0025; 0026
(2017/08/28)
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- Chiral: N, N ′-dioxide/Co(II)-promoted asymmetric 1,3-dipolar cycloaddition of nitrones with methyleneindolinones
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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).
- Zhang, Dong,Yin, Chengkai,Zhou, Yuhang,Xu, Yali,Lin, Lili,Liu, Xiaohua,Feng, Xiaoming
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supporting information
p. 7925 - 7928
(2017/07/22)
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- Synthesis of 2,3-Disubstituted NH Indoles via Rhodium(III)-Catalyzed C-H Activation of Arylnitrones and Coupling with Diazo Compounds
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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.
- Guo, Xin,Han, Jianwei,Liu, Yafeng,Qin, Mingda,Zhang, Xueguo,Chen, Baohua
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p. 11505 - 11511
(2017/11/10)
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- Synthesis of Benzimidazolones via One-Pot Reaction of Hydroxylamines, Aldehydes, and Trimethylsilyl Cyanide Promoted by Diacetoxyiodobenzene
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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.
- Zhang, Huaiyuan,Huang, Danfeng,Wang, Ke-Hu,Li, Jun,Su, Yingpeng,Hu, Yulai
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p. 1600 - 1609
(2017/02/10)
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- 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
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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
- Luo, Qingqing,Cao, Chao-Tun,Cao, Zhongzhong,Cao, Chenzhong
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p. 406 - 413
(2016/07/28)
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- Iron-Catalyzed Cyclization of Nitrones with Geminal-Substituted Vinyl Acetates: A Direct [4 + 2] Assembly Strategy Leading to 2,4-Disubstituted Quinolines
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An iron-catalyzed intermolecular [4 + 2] cyclization of arylnitrones with geminal-substituted vinyl acetates was developed for the synthesis of 2,4-disubstituted quinolines in moderate to good yields with good functional group compatibilities. Preliminary mechanistic studies suggest a plausible iron-catalyzed C-H activation process under external-oxidant-free conditions.
- Zhong, Mingbing,Sun, Song,Cheng, Jiang,Shao, Ying
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p. 10825 - 10831
(2016/11/29)
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- An asymmetric pericyclic cascade approach to 3-alkyl-3-aryloxindoles: Generality, applications and mechanistic investigations
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The reaction of L-serine derived N-arylnitrones with alkylarylketenes generates asymmetric 3-alkyl-3-aryloxindoles in good to excellent yields (up to 93%) and excellent enantioselectivity (up to 98% ee) via a pericyclic cascade process. The optimization, scope and applications of this transformation are reported, alongside further synthetic and computational investigations. The preparation of the enantiomer of a Roche anti-cancer agent (RO4999200) 1 (96% ee) in three steps demonstrates the potential utility of this methodology.
- Richmond, Edward,Ling, Kenneth B.,Duguet, Nicolas,Manton, Lois B.,elebi-?lcüm, Nihan,Lam, Yu-Hong,Alsancak, Sezen,Slawin, Alexandra M. Z.,Houk,Smith, Andrew D.
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supporting information
p. 1807 - 1817
(2015/02/19)
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- Rhodium-catalyzed cyclization of diynes with nitrones: A formal [2+2+5] approach to bridged eight-membered heterocycles
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N-aryl-substituted nitrones were employed as fiveatom coupling partners in the rhodium-catalyzed cyclization with diynes. In this reaction, the nitrone moiety served as a directing group for the catalytic C-H activation of the N-aryl ring. This formal [2+2+5] approach allows rapid access to bridged eight-membered heterocycles with broad substrate scope. The results of this study may provide new insight into the chemistry of nitrones and find applications in the synthesis of other heterocycles,.
- Wang, Chunxiang,Wang, Dongping,Yan, Hao,Wang, Haolong,Pan, Bin,Xin, Xiaoyi,Li, Xincheng,Wu, Fan,Wan, Boshun
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supporting information
p. 11940 - 11943
(2015/01/09)
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- Remarkable stereocontrol in 1,3-dipolar cycloaddition of acyclic nitrones: Investigation of the cycloaddition of C,N-diaryl nitrones to methyl cinnamate under different reaction conditions
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Investigation of the cycloaddition of C,N-diarylnitrones to methyl cinnamate under different reaction conditions were carried out. Two diastereoisomeric and one regioisomeric cycloadducts were isolated and characterized by spectroscopic and X-ray data. Re
- Biswas, Pizush Kanti,Bandyopadhyay, Debasish,Prange, Thierry,Neuman, Alain,Banerji, Avijit
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experimental part
p. 1146 - 1159
(2011/05/06)
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- A highly stereoselective synthesis of chiral α-amino-β-lactams via the Kinugasa reaction employing ynamides
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(Chemical Equation Presented) A highly stereoselective synthesis of chiral α-amino-β-lactam through an ynamide-Kinugasa reaction is described. In addition, a mechanistic model is illustrated here to rationalize the observed diastereoselectivity, which depends on both the initial [3 + 2] cycloaddition step and the subsequent protonation for which both are highly selective.
- Zhang, Xuejun,Hsung, Richard P.,Li, Hongyan,Zhang, Yu,Johnson, Whitney L.,Figueroa, Ruth
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supporting information; experimental part
p. 3477 - 3479
(2009/05/27)
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- Enantioselective 1,3-dipolar cycloaddition of nitrones with ethyl vinyl ether: The difference between Bronsted and Lewis acid catalysis
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(Chemical Equation Presented) Bronsted and Lewis face off: A new chiral N-triflyl phosphoramide is used for asymmetric 1,3-dipolar cycloaddition of diaryl nitrones to ethyl vinyl ether to give the endo products in up to 93% ee (see scheme; Tf = trifluoromethanesulfonyl; Ad = adamantyl). The structure of the chiral phosphoramide was confirmed by X-ray crystallographic analysis.
- Jiao, Peng,Nakashima, Daisuke,Yamamoto, Hisashi
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p. 2411 - 2413
(2008/12/23)
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- 1,3-Dipolar cycloadditions: Investigation of cycloadditions of C-aryl-N-(4-chlorophenyl) nitrones to N-cinnamoyl piperidines
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(Chemical Equation Presented) Investigation of cycloadditions of C-aryl-N-(4-chlorophenyl)nitrones to N-cinnamoyl piperidines was carried out. Two diastereoisomeric and one regioisomeric cycloadducts, and in some cases ring-opened compounds were character
- Banerji, Avijit,Biswas, Pizush Kanti,Bandyopadhyay, Debasish,Gupta, Maya,Prange, Thierry,Neuman, Alain
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p. 137 - 143
(2008/03/27)
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- 1,3-Dipolar cycloadditions. Part-XIII: Microwave irradiation assisted synthesis and spectroscopic investigations of C-aryl-N-phenyl and C-aryl-N-(4′-chlorophenyl)nitrones
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C-Aryl-N-phenylnitrones have been prepared in very high yields from N-phenylhydroxylamine and aryl aldehydes using the microwave irradiation technique within a few minutes. The synthesis of a new series of nitrones, viz. the series of C-aryl-N-(4′-chlorop
- Banerji, Avijit,Biswas, Pizush Kanti,Gupta, Maya,Saha, Rina,Banerji, Julie
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p. 1004 - 1010
(2008/09/19)
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- Synthesis of C, N-diaryl nitrones from the reduction of nitroarene with aromatic aldehydes promoted by metallic samarium
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A mild and facile reduction of nitroarene with aromatic aldehydes promoted by metallic samarium to C, N-diaryl nitrones in moderate yields has been developed.
- Jia, Xueshun,Li, Dafeng,Huang, Qing,Zhu, Li,Li, Jian
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p. 308 - 309
(2008/02/08)
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- 1,3-Dipolar cycloaddition reactions of nitrones to prop-1-ene-1,3-sultone
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The reaction of prop-1-ene-1,3-sultone (1) with a variety of nitrones 2 afforded novel [3+2] cycloaddition products 3, 4, and 5 in good yield. Excellent regio- and stereoselectivity were achieved in the cycloaddition reaction with phenylnitrones.
- Tian, Li,Xu, Guo-Yan,Ye, Yong,Liu, Lun-Zu
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p. 1329 - 1334
(2007/10/03)
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- The effects of lewis acid on the 1,3-dipolar cycloaddition reaction of C-arylaldonitrones with alkenes
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The regio- and stereoselectivity of the 1,3-dipolar cycloaddition reactions of C-aryl-N-alkylaldonitrones (1a-e) with some alkenes were found to be affected significantly by the addition of Lewis acid. The rate of the reaction was also affected by adding the Lewis acid. In the reactions using allyl alcohol as a dipolarophile an addition of Lewis acid caused a remarkable acceleration of the reaction and a great change in the stereoselectivity. In the reactions using ethyl acrylate as a dipolarophile the regioselectivity was reversed whether the reaction was performed in the presence or the absence of Lewis acid; i.e. isoxazolidine-5-carboxylates were obtained mainly in the absence of Lewis acid although isoxazolidine-4-carboxylates were obtained mainly in the presence of Lewis acid. When the reaction of C,N-diarylaldonitrones (1k, 1m, 1n) with ethyl acrylate was carried out in the presence of Lewis acid, the cleavage of the N-O bond of the cycloadducts giving γ-aminoalcohols was also observed besides a reverse phenomenon of regioselectivity.
- Shimizu, Tomio,Ishizaki, Masaya,Nitada, Nobuo
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p. 908 - 921
(2007/10/03)
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- α-(trifluoromethyl)amine derivatives via nucleophilic trifluoromethylation of nitrones
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(Trifluoromethyl)trimethylsilane (TMSCF3) reacts with nitrones to afford α-(trifluoromethyl)hydroxylamines protected as O-trimethylsilyl ethers. Potassium t-butoxide initiates the nucleophilic trifluoromethylation. The reaction works best with α,N-diaryl nitrones, and the conditions are compatible with a range of substituents on the aryl groups. Acidic deprotection of the nitrone/TMSCF3 adducts generates α-(trifluoromethyl)hydroxylamines. Catalytic hydrogenation of the adducts produces α-(trifluoromethyl)amines. Nitrone/TMSCF3 adducts with strong electron-withdrawing groups on the α-aryl ring or heterocyclic α-aryl groups undergo an elimination/addition sequence to generate α, α-bis(trifluoromethyl)amines. Nitrones with alkyl groups bound directly to the 1,3-dipolar moiety fail to react with TMSCF3, but trifluoromethylation of β,γ-unsaturated nitrones followed by reduction of the double bond can circumvent this limitation.
- Nelson,Owens,Hiraldo
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p. 2572 - 2582
(2007/10/03)
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- Synthesis and characterization of model ultimate carcinogens/metabolites derived from lead tetraacetate oxidation of arylnitrones: 2′-Deoxyguanosine adducts
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The synthesis of model reactive metabolites 4a-c by lead tetraacetate (LTA) oxidation of arylnitrones 3a-c is described. Compounds 4a-c react with deoxyguanosine (dG) to give N-benzoylated C8-adducts 5a-c. Following debenzoylation with the heterogeneous system (sodium carbonate/methanol) leads to the corresponding C8-adducts 6a-c.
- Mallesha,Kumar,Mantelingu,Rangappa
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p. 1459 - 1461
(2007/10/03)
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- 13C and 1H NMR of Arylnitrones. Substituent Effects of α-Phenyl-N-(p-substituted phenyl)nitrones
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Substituent effects on the chemical shifts of the conjugation sites in α-phenyl-N-arylnitrones (2) have been investigated.Resonance effects predominate at these positions.The electronic effects of the substituents should be treated separately between electron-donating groups and electron-donating groups and electron-withdrawing ones.A plausible mechanism for the transmission of substituent effects in 2 has been proposed.
- Suda, Kohji,Tsujimoto, Toshio,Yamauchi, Masashige
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p. 3607 - 3612
(2007/10/02)
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- Improved Preparation of α,N-Diphenylnitrones and N-Benzyl-N-Phenylhydroxylamines by direct Oxidation of Secondary Anilines
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A simple and rapid method for the oxidation of secondary anilines to α,N-diphenylnitrones and the subsequent reduction to secondary N-benzyl-N-phenylhydroxylamines is described.
- Gorrod, John W.,Gooderham, Nigel J.
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p. 261 - 265
(2007/10/02)
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