31791-98-7Relevant academic research and scientific papers
Rhodium(III)-catalyzed C4-amidation of indole-oximes with dioxazolones: Via C-H activation
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)
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
Rhodium(iii)-catalyzed cascade reactions of benzoic acids with dioxazolones: Discovery of 2,5-substituted benzoxazinones as AIE molecules
Li, Jinbiao,Zhang, Shuaizhong,Lonka, Madhava Reddy,Zhang, Jinquan,Zou, Hongbin
supporting information, p. 11203 - 11206 (2019/09/30)
A rhodium-catalyzed cascade reaction of benzoic acids with 1,4,2-dioxazol-5-ones was studied. The carboxyl group enabled a double C-H amidation followed by further intramolecular cyclization to afford 2,5-substituted benzoxazinones, which exhibited aggregation-induced emission (AIE) properties with a promising excited-state intramolecular proton-transfer (ESIPT) phenomenon.
Experimental and computational studies on H2O-promoted, Rh-catalyzed transient-ligand-free ortho-C(sp2)-H amidation of benzaldehydes with dioxazolones
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)
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.
Product Control using Substrate Design: Ruthenium-Catalysed Oxidative C?H Olefinations of Cyclic Weinreb Amides
Das, Riki,Kapur, Manmohan
supporting information, p. 16986 - 16990 (2016/11/17)
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.
Rhodium-catalyzed C-H alkynylation of arenes at room temperature
Feng, Chao,Loh, Teck-Peng
supporting information, p. 2722 - 2726 (2014/03/21)
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.
Rhodium(iii)-catalyzed formal oxidative [4 + 1] cycloaddition of benzohydroxamic acids and α-diazoesters. A facile synthesis of functionalized benzolactams
Lam, Hon-Wah,Man, Ka-Yi,Chan, Wai-Wing,Zhou, Zhongyuan,Yu, Wing-Yiu
supporting information, p. 4112 - 4116 (2014/06/10)
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.
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.
Synthesis of hydroxamic acids by using the acid labile O-2-methylprenyl protecting group
Nikitjuka, Anna,Jirgensons, Aigars
supporting information, p. 2972 - 2974 (2013/02/22)
Coupling of carboxylic acids with O-2-methylprenyl hydroxylamine provided O-protected hydroxamic acids, which could be deprotected by treatment with trifluoroacetic acid (TFA) in dichloromethane giving volatile by-products. Protected hydroxamic acids could be N-arylated or alkylated followed by deprotection to give N-substituted hydroxamic acids. Georg Thieme Verlag KG · Stuttgart · New York.
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.
Antibacterial alkoxybenzamide inhibitors of the essential bacterial cell division protein FtsZ
Czaplewski, Lloyd G.,Collins, Ian,Boyd, E. Andrew,Brown, David,East, Stephen P.,Gardiner, Mihaly,Fletcher, Rowena,Haydon, David J.,Henstock, Vincent,Ingram, Peter,Jones, Clare,Noula, Caterina,Kennison, Leanne,Rockley, Chris,Rose, Valerie,Thomaides-Brears, Helena B.,Ure, Rebecca,Whittaker, Mark,Stokes, Neil R.
scheme or table, p. 524 - 527 (2011/02/28)
3-Methoxybenzamide is a weak inhibitor of the essential bacterial cell division protein FtsZ. Exploration of the structure-activity relationships of 3-methoxybenzamide analogues led to the identification of potent anti-staphylococcal compounds.
