31791-97-6Relevant academic research and scientific papers
Mono- and ditopic hydroxamate ligands towards discrete and extended network architectures
Fugu, Mohammed B.,Ellaby, Rebecca J.,O'Connor, Helen M.,Pitak, Mateusz B.,Klooster, Wim,Horton, Peter N.,Coles, Simon J.,Al-Mashhadani, Mohammed H.,Perepichka, Igor F.,Brechin, Euan K.,Jones, Leigh F.
supporting information, p. 10180 - 10190 (2019/07/15)
A family of mono- and ditopic hydroxamic acids has been employed in the synthesis and structural and physical characterisation of discrete (0D) and (1- and 2-D) extended network coordination complexes. Examples of the latter include the 1-D coordination p
Consecutive Lossen rearrangement/transamidation reaction of hydroxamic acids under catalyst- and additive-free conditions
Jia, Mengmeng,Zhang, Heng,Lin, Yongjia,Chen, Dimei,Chen, Yanmei,Xia, Yuanzhi
, p. 3615 - 3624 (2018/05/26)
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.
Tf2NH-Catalyzed Formal [3 + 2] Cycloaddition of Ynamides with Dioxazoles: A Metal-Free Approach to Polysubstituted 4-Aminooxazoles
Zhao, Yingying,Hu, Yancheng,Wang, Chunxiang,Li, Xincheng,Wan, Boshun
, p. 3935 - 3942 (2017/04/11)
An unprecedented Tf2NH-catalyzed formal [3 + 2] cycloaddition of ynamides with dioxazoles was developed to construct various polysubstituted 4-aminooxazoles. This approach features a metal-free catalytic bimolecular assembly of oxazole motifs, a low-cost catalyst, exceptionally mild reaction conditions, a very short reaction time, a broad substrate scope, and high efficiency. This metal-free protocol may find applications in pharmaceutical-oriented synthesis.
An efficient method for the preparation of hydroxamic acids
Gao, Xi-Ai,Wang, Xian-Xue,Yan, Hao,Li, Jian,Yan, Ru-Long,Huang, Guo-Sheng
, p. 381 - 385 (2013/05/22)
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.
Benzohydroxamic acids as potent and selective anti-HCV agents
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)
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.
A convenient one-pot synthesis of aryl amines from aryl aldoximes mediated by Koser's reagent
Ghosh, Harisadhan,Baneerjee, Arghya,Rout, Saroj Kumar,Patel, Bhisma K.
experimental part, p. 209 - 216 (2011/05/30)
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.
Syntheses and biological activity studies of novel sterol analogs from nitroso diels-alder reactions of ergosterol
Yang, Baiyuan,Miller, Patricia A.,Moellmann, Ute,Miller, Marvin J.
body text, p. 2828 - 2831 (2009/12/06)
A serles of novel sterol analogs was prepared using nitroso Dlels-Alder reactions with ergosterol. Most cycloaddltlon reactions proceeded In an excellent reglo- and stereoselective fashion. Further N-O bond cleavage of cycloadducts generated compounds with biological activity In PC-3 and MCF-7 cancer cell lines
Acylation of Amines and Alcohols by Anodic Oxidation of N-Phenyl-hydroxamic Acids
Masui, Masaichiro,Ueshima, Takahiro,Yamazaki, Tomoko,Ozaki, Shigeko
, p. 2130 - 2133 (2007/10/02)
The electrochemical acylation of amines and alcohols is described.The yield of products from the electrochemical reaction is markedly improved by the use of N-phenyl derivatives of hydroxamic acids in place of the N-hydrogen counterparts.Keywords - anodic oxidation; acylation of amine and alcohol; N-phenylhydroxamic acid; acetonitrile; glassy-carbon electrode
