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Cu(II)-Catalyzed C-H Amidation/Cyclization of Azomethine Imines with Dioxazolones via Acyl Nitrenes: A Direct Access to Diverse 1,2,4-Triazole Derivatives
We report a Cu(II)-catalyzed C-H amidation/cyclization of azomethine imines with dioxazolones as acyl nitrene transfer reagents under additive-and ligand-free conditions. An array of 1,2,4-triazolo[1,5-a]pyridine derivatives were afforded in moderate to good yields with excellent functional group tolerance. In addition, scale-up reaction and photoluminescence properties were discussed.
Liu, Xiang,Li, Wen,Jiang, Wenxuan,Lu, Hao,Liu, Jiali,Lin, Yijun,Cao, Hua
supporting information
p. 613 - 618
(2022/01/20)

Silver-Catalyzed Acyl Nitrene Transfer Reactions Involving Dioxazolones: Direct Assembly of N-Acylureas
Dioxazolones and isocyanides are useful synthetic building blocks, and have attracted significant attention from researchers. However, the silver-catalyzed nitrene transfer reaction of dioxazolones has not been investigated to date. Herein, a silver-catalyzed acyl nitrene transfer reaction involving dioxazolones, isocyanides, and water was realized in the presence of Ag2O to afford a series of N-acylureas in moderate to good yields.
Yang, Zheng-Lin,Xu, Xin-Liang,Chen, Xue-Rong,Mao, Zhi-Feng,Zhou, Yi-Feng
supporting information
p. 648 - 652
(2020/12/21)

P(III)-Assisted Electrochemical Access to Ureas via in situ Generation of Isocyanates from Hydroxamic Acids
An external oxidant-free protocol for the generation of isocyanates from hydroxamic acids assisted by trivalent phosphine under mild electrochemical conditions was reported. The process started with the anodic oxidation of hydroxamic acids, followed by reacting with phosphine to form corresponding alkoxyphosphoniums and subsequent rearrangement with the release of tri-substituted phosphine oxide as the driving force to give isocyanates, which were trapped by N-based nucleophiles to produce various ureas. This method provides a broadly applicable procedure to access isocyanate intermediates under mild electrochemical conditions.
Meng, Haiwen,Sun, Kunhui,Xu, Zhimin,Tian, Lifang,Wang, Yahui
supporting information
p. 1768 - 1772
(2021/03/26)

Palladium-Catalyzed 5-exo-dig Cyclization Cascade, Sequential Amination/Etherification for Stereoselective Construction of 3-Methyleneindolinones
An cascade intramolecular 5-exo-dig cyclization of N-(2-iodophenyl)propiolamides and sequential amination/etherification (with N-hydroxybenzamides, phenyl hydroxycarbamate) protocol for the synthesis of amino- and phenoxy-substituted 3-methyleneindolinones using unexpensive Pd(PPh3)4 as catalyst has been developed. The protocol enables the assembly of structurally important oxindole cores featuring moderate functional group tolerance (particularly the halo group), affording a broad spectrum of products with diverse substituents in good to excellent yields. (Figure presented.).
Zuo, Youpeng,He, Xinwei,Tang, Qiang,Hu, Wangcheng,Zhou, Tongtong,Hu, Wenbo,Shang, Yongjia
p. 2117 - 2123
(2020/12/22)

Synthesis of sulfimides and N-Allyl-N-(thio)amides by Ru(II)catalyzed nitrene transfer reactions of N-acyloxyamides
The N-acyloxyamides were employed as effective N-acyl nitrene precursors in reactions with thioethers under the catalysis of a commercially available Ru(II) complex, from which a variety of sulfimides were synthesized efficiently and mildly. If an allyl group is contained in the thioether precursor, the [2,3]-sigmatropic rearrangement of the sulfimide occurs simultaneously and the N-allyl-N-(thio)amides were obtained as the final products. Preliminary mechanistic studies indicated that the Ru-nitrenoid species should be a key intermediate in the transformation.
Zhang, Xinyu,Lin, Bo,Chen, Jianhui,Chen, Jiajia,Luo, Yanshu,Xia, Yuanzhi
supporting information
p. 819 - 825
(2021/02/01)

Stepwise Evolution of Fragment Hits against MAPK Interacting Kinases 1 and 2
Dysregulation of translation initiation factor 4E (eIF4E) activity occurs in various cancers. Mitogen-activated protein kinase (MAPK) interacting kinases 1 and 2 (MNK1 and MNK2) play a fundamental role in activation of eIF4E. Structure-activity relationship-driven expansion of a fragment hit led to discovery of dual MNK1 and MNK2 inhibitors based on a novel pyridine-benzamide scaffold. The compounds possess promising in vitro and in vivo pharmacokinetic profiles and show potent on target inhibition of eIF4E phosphorylation in cells.
Kwiatkowski, Jacek,Liu, Boping,Pang, Shermaine,Ahmad, Nur Huda Binte,Wang, Gang,Poulsen, Anders,Yang, Haiyan,Poh, Yong Rui,Tee, Doris Hui Ying,Ong, Esther,Retna, Priya,Dinie, Nurul,Kwek, Perlyn,Wee, John Liang Kuan,Manoharan, Vithya,Low, Choon Bing,Seah, Peck Gee,Pendharkar, Vishal,Sangthongpitag, Kanda,Joy, Joma,Baburajendran, Nithya,Jansson, Anna Elisabet,Nacro, Kassoum,Hill, Jeffrey,Keller, Thomas H.,Hung, Alvin W.
supporting information
p. 621 - 637
(2020/02/05)

Palladium-catalyzed cascade decarboxylative amination/6- endo-dig benzannulation of o-alkynylarylketones with n-hydroxyamides to access diverse 1-naphthylamine derivatives
An efficient and practical one-pot strategy to produce highly substituted 1-naphthylamines via sequential palladium-catalyzed decarboxylative amination/intramolecular 6-endo-dig benzannulation reactions has been described. In this reaction, a broad range of electron-rich, electron-neutral, and electron-deficient o-alkynylarylketones react well with N-hydroxyl aryl/alkylamides to give a diversity of 1-naphthylamines in good to excellent yields under mild reaction conditions. The gram-scale synthesis, with benefits such as undiminished product yield and easy transformation, illustrated the practicality of this method.
Zuo, Youpeng,He, Xinwei,Tang, Qiang,Hu, Wangcheng,Zhou, Tongtong,Shang, Yongjia
p. 3890 - 3894
(2020/05/18)

Divergent Synthesis of Tunable Cyclopentadienyl Ligands and Their Application in Rh-Catalyzed Enantioselective Synthesis of Isoindolinone
A series of rhodium complexes bearing sterically and electronically tunable cyclopentadienyl ligands, prepared by utilizing Co2(CO)8-mediated [2+2+1] cyclization as a key step, were synthesized. In the presence of 2.5 mol% of CpmRh4, unprecedented enantioselective [4+1] annulation reaction of benzamides and alkenes was achieved with a broad substrate scope under mild reaction conditions, providing a variety of isoindolinones with excellent regio-and enantioselectivity (up to 94% yield, 97:3 er). Preliminary mechanistic studies suggest that the reaction involves an oxidative Heck reaction and an intramolecular enantioselective alkene hydroamination reaction.
Cui, Wen-Jun,Wu, Zhi-Jie,Gu, Qing,You, Shu-Li
p. 7379 - 7385
(2020/08/19)

RhIII-Catalyzed C?H Activation of Aryl Hydroxamates for the Synthesis of Isoindolinones
RhIII-catalyzed C?H functionalization reaction yielding isoindolinones from aryl hydroxamates and ortho-substituted styrenes is reported. The reaction proceeds smoothly under mild conditions at room temperature, and tolerates a range of functional groups. Experimental and computational investigations support that the high regioselectivity observed for these substrates results from the presence of an ortho-substituent embedded in the styrene. The resulting isoindolinones are valuable building blocks for the synthesis of bioactive compounds. They provide easy access to the natural-product-like compounds, isoindolobenzazepines, in a one-pot two-step reaction. Selected isoindolinones inhibited Hedgehog (Hh)-dependent differentiation of multipotent murine mesenchymal progenitor stem cells into osteoblasts.
Shaaban, Saad,Davies, Caitlin,Merten, Christian,Flegel, Jana,Otte, Felix,Strohmann, Carsten,Waldmann, Herbert
supporting information
p. 10729 - 10734
(2020/07/25)

Rhodium(III)-catalyzed C4-amidation of indole-oximes with dioxazolones: Via C-H activation
A novel method for the Rh(III)-catalyzed oxime-directed C-H amidation of indoles with dioxazolones has been developed. This strategy provides an exclusive site selectivity and the directing group can be easily removed. This transformation features a wide substrate scope, good functional group tolerance and excellent yields, and may serve as a significant tool to construct structurally diverse indole derivatives for the screening of potential pharmaceuticals in the future. This journal is
Deng, Ke-Zuan,Fu, Xiao-Pan,Ji, Ya-Fei,Tang, Shi-Biao,Wu, Gao-Rong,Xia, Cheng-Cai,Yang, Jin-Yue,Zhang, Li-Li
supporting information
p. 7922 - 7931
(2020/11/02)

Vinylphosphonium Salt-Mediated Reactions: A One-Pot Condensation Approach for the Highly cis-Selective Synthesis of N-Benzoylaziridines and the Green Synthesis of 1,4,2-Dioxazoles as Two Important Classes of Heterocyclic Compounds
An efficient, one-pot, and convenient approach for the reaction of the same precursors, trialkyl(aryl) phosphines, acetylene diesters, and benzhydroxamic acids has been developed to produce two important classes of heterocyclic compounds: N-benzoylaziridines and 1,4,2-dioxazoles. The strategy utilizes the intermediate solvation as a key step in product selectivity. The usefulness of the developed approach has been confirmed in the unprecedented highly cis-selective formation of the N-benzoylaziridines. In addition, the procedure provides a green alternative method for the synthesis of 1,4,2-dioxazoles employing a β-cyclodextrin nanoreactor in aqueous media.
Aghahosseini, Hamideh,Ramazani, Ali,Jalayer, Nastaran Safarvand,Ranjdoost, Zahra,Souldozi, Ali,?lepokura, Katarzyna,Lis, Tadeusz
supporting information
p. 22 - 26
(2019/01/11)

Dioxazolones as masked ester surrogates in the Pd(ii)-catalyzed direct C-H arylation of 6,5-fused heterocycles
A simple and effective Pd(ii)-catalyzed regioselective C(2)-H arylation of 6,5-fused heterocycles with dioxazolones as a masked ester surrogate under mild conditions is reported. The significance of the arylation is highlighted by the new reactivity demonstrated in dioxazolones via proximal C-H activation of the cyclic carbonate of the hydroxamic acid functionality under protic conditions.
Saxena, Paridhi,Maida, Neha,Kapur, Manmohan
supporting information
p. 11187 - 11190
(2019/09/30)

Consecutive Lossen rearrangement/transamidation reaction of hydroxamic acids under catalyst- and additive-free conditions
The Lossen rearrangement is a classic process for transforming activated hydroxamic acids into isocyanate under basic or thermal conditions. In the current report we disclosed a consecutive Lossen rearrangement/transamidation reaction in which unactivated hydroxamic acids were converted into N-substituted formamides in a one-pot manner under catalyst- and additive-free conditions. One feature of this novel transformation is that the formamide plays triple roles in the reaction by acting as a readily available solvent, a promoter for additive-free Lossen rearrangement, and a source of the formyl group in the final products. Acyl groups other than formyl could also be introduced into the product when changing the solvent to other low molecular weight aliphatic amide derivatives. The solvent-promoted Lossen rearrangement was better understood by DFT calculations, and the intermediacy of isocyanate and amine was supported well by experiments, in which the desired products were obtained in excellent yields under similar conditions. Not only monosubstituted formamides were synthesized from hydroxamic acids, but also N,N-disubstituted formamides were obtained when secondary amines were used as precursors.
Jia, Mengmeng,Zhang, Heng,Lin, Yongjia,Chen, Dimei,Chen, Yanmei,Xia, Yuanzhi
p. 3615 - 3624
(2018/05/26)

Experimental and computational studies on H2O-promoted, Rh-catalyzed transient-ligand-free ortho-C(sp2)-H amidation of benzaldehydes with dioxazolones
An efficient and convenient ligand-free, rhodium-catalyzed ortho-C(sp2)-H amidation of benzaldehydes with dioxazolones using H2O as the key promoter is described. Using this protocol, a wide range of benzaldehyde substrates were selectively amidated in good to excellent yields with broad functional group compatibility. KIE experiments revealed that the C-H bond activation was likely the rate-limiting step. In addition, computational studies indicated that the catalyst precursor interacted with water and dioxazolones to generate the active catalytic species. Notably, the practicality and efficacy of this method were illustrated by a late-stage amidation of an estrone-derived molecule and further transformations of the amidated product.
Ding, Jun,Jiang, Wei,Bai, He-Yuan,Ding, Tong-Mei,Gao, Dafang,Bao, Xiaoguang,Zhang, Shu-Yu
supporting information
p. 8889 - 8892
(2018/08/17)

Synthesis and biological activity of salinomycin-hydroxamic acid conjugates
Several salinomycin-hydroxamic acid conjugates were designed and synthesized. Most conjugates showed better antiproliferative activities than salinomycin in HT-29 colon cancer, HGC-27 gastric cancer, and especially in MDA-MB-231 triple-negative human breast cancer cells. These conjugates are stable in cell culture media, and they showed much better biological activities than the 1:1 physical mixture with hydroxamic acids and salinomycin. The better membrane permeability and hydrolysis rate of the conjugates may lead to the activity improvements.
Li, Bo,Wu, Jun,Zhang, Wenxuan,Li, Zhongwen,Chen, Gang,Zhou, Qi,Wu, Song
p. 1624 - 1626
(2017/03/16)

A base-mediated self-propagative Lossen rearrangement of hydroxamic acids for the efficient and facile synthesis of aromatic and aliphatic primary amines
A variety of aromatic and aliphatic hydroxamic acids were converted to the corresponding primary amines via base-mediated rearrangement. This rearrangement could proceed with less than 1 equiv. of K2CO3 in polar solvents under thermal conditions with no external reagents. This rearrangement has several features including no external activating agents needed for promoting the rearrangement, less than one equivalent of a base is sufficient for the reaction, and a clean reaction in which only carbon dioxide is produced as a by-product. A self-propagating mechanism via an isocyanate intermediate is proposed and elementary reaction steps, namely, chain propagation reactions are supported by experiments.
Ohtsuka, Naoya,Okuno, Moriaki,Hoshino, Yujiro,Honda, Kiyoshi
supporting information
p. 9046 - 9054
(2016/10/05)

Product Control using Substrate Design: Ruthenium-Catalysed Oxidative C?H Olefinations of Cyclic Weinreb Amides
A new class of Weinreb amides has been developed as directing groups for the ruthenium-catalysed regioselective oxidative C?H olefination. The new Weinreb amides successfully inhibit the N?O bond reductive cleavage usually associated with the cationic ruthenium system, thereby keeping intact the synthetic utility of Weinreb amides. Mechanistic studies reveal interesting aspects of the directing group capabilities of Weinreb amides when compared to simple amides of similar structures.
Das, Riki,Kapur, Manmohan
supporting information
p. 16986 - 16990
(2016/11/17)

One-pot synthesis of primary amines from carboxylic acids through rearrangement of in situ generated hydroxamic acid derivatives
A one-pot synthesis of primary amines from carboxylic acids through a Lossen rearrangement of hydroxamic acid derivatives, which were in situ generated by the reaction of carboxylic acids with O-trimethylsilylhydroxylamine (NH2OTMS) and carbonyl diimidazole (CDI, 1.5 equiv) in dimethyl sulfoxide at room temperature, has been achieved. This one-pot method could be applied to various carboxylic acids such as aromatic, heteroaromatic, aliphatic, and optically active substrates.
Hoshino, Yujiro,Ohtsuka, Naoya,Okada, Takuya,Honda, Kiyoshi
supporting information
p. 5304 - 5307
(2016/11/16)

Design and synthesis of dihydroisoquinolones for fragment-based drug discovery (FBDD)
This study describes general synthesis aspects of fragments for FBDD, as illustrated by the dihydroisoquinolones 1-3. Previous Rh(iii) methodology is extended to incorporate amines, heteroatoms (N and S), and substituents (halogen, ester) as potential binding groups and/or synthetic growth points for fragment-to-lead elaboration.
Palmer, Nick,Peakman, Torren M.,Norton, David,Rees, David C.
p. 1599 - 1610
(2016/02/10)

Racemization free longer N-terminal peptide hydroxamate synthesis on solid support using ethyl 2-(tert-butoxycarbonyloxyimino)-2-cyanoacetate
A facile, efficient, racemization-free, and environment friendly protocol for the synthesis of peptide hydroxamic acids directly from carboxylic/amino acids by ethyl 2-(tert-butoxycarbonyloxyimino)-2-cyanoacetate in the presence of DIPEA/DMAP at room temperature is described. The compatibility of this method with Fmoc based solid phase peptide synthesis (SPPS) is also demonstrated by synthesizing three relatively large N-terminal peptide hydroxamic acids on resin. Also, some biologically important hydroxamates are synthesized using this protocol.
Manne, Srinivasa Rao,Thalluri, Kishore,Giri, Rajat Subhra,Paul, Ashim,Mandal, Bhubaneswar
supporting information
p. 6108 - 6111
(2015/10/28)

A two-step tandem reaction to prepare hydroxamic acids directly from alcohols
The first synthesis of hydroxamic acids from alcohols has been developed. Both benzylic and aliphatic alcohols can be tolerated and applied in this reaction. The methodology is economical, environmentally benign and high yielding. This journal is
Dettori, Giovanna,Gaspa, Silvia,Porcheddu, Andrea,De Luca, Lidia
supporting information
p. 4582 - 4585
(2014/06/24)

Rhodium-catalyzed C-H alkynylation of arenes at room temperature
The rhodium(III)-catalyzed ortho C-H alkynylation of non-electronically activated arenes is disclosed. This process features a straightforward and highly effective protocol for the synthesis of functionalized alkynes and represents the first example of merging a hypervalent iodine reagent with rhodium(III) catalysis. Notably, this reaction proceeds at room temperature, tolerates a variety of functional groups, and more importantly, exhibits high selectivity for monoalkynylation. Hot rhod: A rhodium-catalyzed, electronically reversed Sonogashira reaction between unbiased arenes and the hypervalent iodine reagent 1 proceeds through C-H activation. This reaction displays excellent functional-group tolerance and high efficiency, and thus opens a new synthetic pathway to access functionalized alkynes. Cp=C5Me5, DCE=1,2-dichloroethane, Piv=pivaloyl, TIPS=triisopropylsilyl.
Feng, Chao,Loh, Teck-Peng
p. 2722 - 2726
(2014/03/21)

Rhodium(iii)-catalyzed formal oxidative [4 + 1] cycloaddition of benzohydroxamic acids and α-diazoesters. A facile synthesis of functionalized benzolactams
A Rh(iii)-catalyzed oxidative [4 + 1] cycloaddition of benzohydroxamic acids and α-diazoesters is achieved to afford benzolactams in up to 93% yields. With the N-OAc amido moiety as a directing group, the ortho-C-H is selectively functionalized and the catalytic reaction exhibits excellent tolerance to different functional substituents. A notable rhodacyclic complex is isolated and structurally characterized, suggesting that C-H/N-H cyclometallation is a key step in the catalytic cycle. This journal is the Partner Organisations 2014.
Lam, Hon-Wah,Man, Ka-Yi,Chan, Wai-Wing,Zhou, Zhongyuan,Yu, Wing-Yiu
supporting information
p. 4112 - 4116
(2014/06/10)

N-methylimidazole-catalyzed synthesis of carbamates from hydroxamic acids via the lossen rearrangement
An efficient, one-pot, N-methylimidazole (NMI) accelerated synthesis of aromatic and aliphatic carbamates via the Lossen rearrangement is reported. NMI is a catalyst for the conversion of isocyanate intermediates to the carbamates. Moreover, the utility of arylsulfonyl chloride in combination with NMI minimizes the formation of often-observed hydroxamate-isocyanate dimers during the sequence. Under the present conditions, lowering of temperatures is also possible, enabling a mild protocol.
Yoganathan, Sabesan,Miller, Scott J.
supporting information
p. 602 - 605
(2013/04/11)

Benzohydroxamic acids as potent and selective anti-HCV agents
A diverse collection of 40 derivatives of benzohydroxamic acid (BHAs) of various structural groups were synthesized and tested against hepatitis C virus (HCV) in full-genome replicon assay. Some of these compounds demonstrated an exceptional activity, suppressing viral replication at sub-micromolar concentrations. The compounds were inactive against key viral enzymes NS3, and NS5B in vitro assays, suggesting host cell inhibition target(s). The testing results were consistent with metal coordination by the BHAs hydroxamic group in complex with a target(s). Remarkably, this class of compounds did not suppress poliomyelitis virus (PV) propagation in RD cells indicating a specific antiviral activity of BHAs against HCV.
Kozlov, Maxim V.,Kleymenova, Alla A.,Romanova, Lyudmila I.,Konduktorov, Konstantin A.,Smirnova, Olga A.,Prasolov, Vladimir S.,Kochetkov, Sergey N.
supporting information
p. 5936 - 5940
(2013/10/22)

An efficient method for the preparation of hydroxamic acids
Reactions of acyl chlorides with hydroxylamine hydrochloride and NaHCO 3 generate the corresponding hydroxamic acid products in ethyl acetate and water at room temperature for 5 min. This is a simple and efficient method to synthesize a wide range of hydroxamic acids from carboxylic acids in excellent yield and high purity after simple post-treatment without chromatographic purification. In this process, the highlights are the simple separation of products and cheaply available reagents.
Gao, Xi-Ai,Wang, Xian-Xue,Yan, Hao,Li, Jian,Yan, Ru-Long,Huang, Guo-Sheng
p. 381 - 385
(2013/05/22)

A convenient one-pot synthesis of aryl amines from aryl aldoximes mediated by Koser's reagent
A simple and convenient procedure has been developed for the synthesis of aromatic amine by a one-pot reaction of aromatic aldoxime with hypervalent iodine(III) reagent [hydroxy(tosyloxy)iodo]benzene (HTIB, Koser's reagent), in an alkaline medium. The aldoxime reacts with Koser's reagent to form an intermediate hydroxamic acid, which then undergoes Lossen type rearrangement to produce the desired amine. Several amines have been prepared which otherwise are difficult to prepare, by the reduction of corresponding nitro compounds. The scopes and limitations of this transformation have been discussed. ARKAT-USA, Inc.
Ghosh, Harisadhan,Baneerjee, Arghya,Rout, Saroj Kumar,Patel, Bhisma K.
experimental part
p. 209 - 216
(2011/05/30)

Hypervalent iodine(III)-mediated oxidation of aldoximes to N-acetoxy or N-hydroxy amides
Treatment of various aliphatic and aromatic aldoximes with the hypervalent iodine(iii) reagents (diacetoxyiodo)benzene (DIB) or Koser's reagent [hydroxy(tosyloxy)iodo]benzene (HTIB) gave, respectively, N-acetoxy or N-hydroxy amides in good yields rather t
Ghosh, Harisadhan,Patel, Bhisma K.
experimental part
p. 384 - 390
(2010/02/15)

1-propanephosphonic acid cyclic anhydride (T3P) as an efficient promoter for the Lossen rearrangement: Application to the synthesis of urea and carbamate derivatives
The synthesis of hydroxamic acids starting from carboxylic acids employing 1-propanephosphonic acid cyclic anhydride (T3P) activation is described. Application of ultrasonication accelerates this conversion. Further, the T3P has also been employed to activate the hydroxamates, leading to isocyanates via the Lossen rearrangement. The isocyanates were trapped with suitable nucleophiles to afford the corresponding ureas and carbamates. Georg Thieme Verlag Stuttgart New York.
Vasantha, Basavalingappa,Hemantha, Hosahalli P.,Sureshbabu, Vommina V.
experimental part
p. 2990 - 2996
(2010/10/21)

Base-mediated rearrangement of free aromatic hydroxamic acids (ArCO-NHOH) to anilines
Without using activating agents, a variety of free aromatic hydroxamic acids could be rearranged to aromatic amines in the presence of base alone. The Royal Society of Chemistry 2009.
Hoshino, Yujiro,Okuno, Moriaki,Kawamura, Eri,Honda, Kiyoshi,Inoue, Seiichi
supporting information; experimental part
p. 2281 - 2283
(2009/09/06)

Convenient synthesis of a library of discrete hydroxamic acids using the hydroxythiophenol (Marshall) resin
Several resins have reportedly been used to synthesize hydroxamic acids except for the hydroxythiophenol (Marshall) resin. Herein, we report the use of the Marshall resin to synthesize hydroxamic acids from carboxylic acids and its application to convert a library of 14 discrete aliphatic and aromatic carboxylic acids including N-protected amino acids to their corresponding hydroxamic acids in good yields.
Choi, Jinil,Park, Jewn Giew,Pang, Yuan-Ping
p. 1103 - 1106
(2008/09/17)

Linear free-energy relationships in the protonation equilibria and acid-base catalysed reaction of 4-substituted benzohydroxamic acids
As part of our investigations on the structure-reactivity relationships in protonation and hydrolysis of hydroxamic acids, we have now studied a series of 4-substituted benzohydroxamic acids (4-X-C6H4.CO.NH(OH), with X=H, Me, OMe, Cl, Br, F and NO2) in aqueous sulfuric acid. Good correlation was observed pointing out the validity of the Hammett equation. The protonation constant, ionization constant and rate constant for acid- and base-catalysed hydrolysis reactions seems are to be related in a linear free-energy (LEER) fashion.
Ghosh, Kallol K.,Tamrakar, Pankaj
p. 1153 - 1168
(2007/10/03)

The Use of N,O-bis(tert-Butoxycarbonyl)-hydroxylamine in the Synthesis of N-Hydroxylamines and Hydroxamic Acids
N,O-bis(tert-butoxycarbonyl)-hydroxylamine has been used in the synthesis of 5-lipoxygenase inhibitor LY280810.In addition, this reagent utilized to synthesize a number of other hydroxylamine and hydroxamic acid derivatives in high yields.
Staszak, Michael A.,Doecke, Christopher W.
p. 6021 - 6024
(2007/10/02)

SYNTHESIS AND STRUCTURE OF HYDROXYISOXAZOLIDINES AND DERIVATIVES OF HYDROXYLAMINE AND ALKENALS
The reactions of N-substituted hydroxylamines with alkenals serve as a method for the synthesis of the corresponding 2-substituted 3(5)-hydroxyisoxazolidines.The reaction pathway is determined by the nature of the substituent attached to the nitrogen atom.Ring-chain isomerism has been detected in these newly obtained compounds.
Zelenin, K. N.,Motorina, I. A.,Sviridova, L. A.,Bezhan, I. P.,Ershov, A. Yu.,et al.
p. 1018 - 1024
(2007/10/02)