62305-65-1Relevant academic research and scientific papers
Structure-directed functional properties of symmetrical and unsymmetrical Br-substituted Schiff-bases
Marin, Luminita,Harabagiu, Valeria,Van Der Lee, Arie,Arvinte, Adina,Barboiu, Mihail
, p. 377 - 385 (2013)
This study deals with the investigation of two low molecular weight Schiff base compounds with bromine end groups, differing only by the presence or absence of one methyl group, with the aim of better understanding the solution and the solid state optical
Chemoselective Reduction of the P=O Bond in the Presence of P–O and P–N Bonds in Phosphonate and Phosphinate Derivatives
Sowa, Sylwia,Pietrusiewicz, K. Micha?
supporting information, p. 923 - 938 (2019/01/22)
Chemoselective reduction of the strong P=O bond in the presence of weaker P–O (ester) and P–N (amide) bonds in phosphonic acid derivatives has constituted an unresolved problem in organophosphorus chemistry for years. This long-standing problem is now solved for biologically relevant α-hydroxy and α-amino phosphonic as well as phosphinic acids esters and amides. The reduction of the P=O bond without concomitant scission of the ester and amide bonds is affected by use of BH3, a mild reducing agent, which affords the corresponding borane protected PIII phosphonite and phosphinite derivatives in one step. A mechanistic rationale is proposed for the role played by neighboring OH and NHR groups in facilitating the reduction, and for the observed chemo- and stereoselectivity. The reduction methodology described opens previously unavailable synthetic options in chemistry of α-functionalized phosphonic and phosphinic acids by offering a unique possibility for direct modifications of oxidation level of the P-center in these compounds.
Acceptorless dehydrogenative construction of CN and CC bonds through catalytic aza-Wittig and Wittig reactions in the presence of an air-stable ruthenium pincer complex
Biswas, Nandita,Das, Kalicharan,Sardar, Bitan,Srimani, DIpankar
, p. 6501 - 6512 (2019/05/24)
The construction of CN bonds was achieved by the dehydrogenative coupling of alcohol and azide via aza-Wittig type reaction. The reaction is catalyzed by an acridine-derived ruthenium pincer complex and does not use any oxidant. The present protocol offers a wide substrate scope, including aliphatic, aryl or heteroaryl alcohol/azides. This expeditious protocol was successfully applied to construct a CC bond directly from alcohol via dehydrogenative Wittig reaction. Furthermore, the synthesis of structurally important pyrrolo[1,4]benzodiazepine derivatives was also achieved by this methodology.
Cross-dehydrogenative coupling strategy for phosphonation and cyanation of secondary N-alkyl anilines by employing 2,3-dichloro-5,6-dicyanobenzoquinone
Liu, Qing,Yu, Shuchen,Hu, Liangzhen,Hussain, Muhamad Ijaz,Zhang, Xiaohui,Xiong, Yan
, p. 7209 - 7217 (2018/11/10)
The cross-dehydrogenative coupling strategy for metal-free phosphonation and cyanation of secondary N-alkyl anilines has been developed firstly under mild reaction conditions. Based on detailed optimization of reaction conditions, the substrate generality of N-alkyl anilines and various hydrogen phosphonates has been investigated, and a series of versatile α-aminophosphonates and α-aminonitriles were therefore furnished in good to excellent yields. A plausible collective reaction mechanism through dehydrogenation to imine formation, then to respective α-aminophosphonates and α-aminonitriles was proposed.
Synthesis of N-benzyl-N-phenylthiophene-2-carboxamide analogues as a novel class of enterovirus 71 inhibitors
Pan, Jiawei,Han, Xin,Sun, Ningyuan,Wu, Haoming,Lin, Dandan,Tien, Po,Zhou, Hai-Bing,Wu, Shuwen
, p. 55100 - 55108 (2015/07/07)
A series of novel human enterovirus 71 inhibitors, N-benzyl-N-phenylthiophene-2-carboxamide analogues, were synthesized and their antiviral activities were evaluated in vitro. Most derivatives of this structure against EV71 had a low micromolar range in the RD (rhabdomyosarcoma) cell lines. The most potent compound 5a, N-(4-bromobenzyl)-N-(4-fluorophenyl)thiophene-2-carboxamide, showed low micromolar activity against EV71 (EC50 = 1.42 μM) compared to the reference anti-EV71 drug enviroxime (EC50 = 0.15 μM). Preliminary SAR studies revealed that the thiophene-2-carboxamide core is crucial for maintaining antiviral activity, and N-substituent phenyl groups largely influenced the anti-EV71 efficacy of this new class of potent antiviral agents.
Biological activity of 3-chloro-azetidin-2-one derivatives having interesting antiproliferative activity on human breast cancer cell lines
Chimento, Adele,Sala, Marina,Gomez-Monterrey, Isabel M.,Musella, Simona,Bertamino, Alessia,Caruso, Anna,Sinicropi, Maria Stefania,Sirianni, Rosa,Puoci, Francesco,Parisi, Ortensia Ilaria,Campana, Carmela,Martire, Emilia,Novellino, Ettore,Saturnino, Carmela,Campiglia, Pietro,Pezzi, Vincenzo
, p. 6401 - 6405 (2013/11/19)
Resveratrol (3,4′,5 tri-hydroxystilbene), a natural plant polyphenol, has gained interest as a non-toxic agent capable of inducing tumor cell death in a variety of cancer types. However, therapeutic application of these beneficial effects remains very lim
GREEN SYNTHESIS OF ARYL ALDIMINES USING ETHYL LACTATE
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Page/Page column 5-6, (2011/08/22)
The present invention relates to a method for preparing aryl aldimines. In particular, the present invention relates to methods of preparing aryl aldimines that uses environmentally friendly solvent systems.
SUBSTITUENT EFFECTS ON THE 31P, 13C, AND 1H NMR CHEMICAL SHIFTS OF SUBSTITUTED DIPHENYL 1-PHENYLAMINO-1-PHENYLMETHANEPHOSPHONATES AND THEIR ANIONS
Smith, Scott J.,Zimmer, Hans,Fluck, Ekkehard,Fischer, Peter
, p. 105 - 120 (2007/10/02)
For a series of thirty-five novel diphenyl 1-phenylamino-1-phenylmethanephosphonates, substituted in the meta and para positions on the anilino and/or aryl ring, 31P chemical shifts show a good linear correlation with Hammett ?n and Taft ?0 parameters, the 31P nucleus being better shielded in the case of electron withdrawing substituents.The same pattern is observed for the phosphonate anions, except when para phenyl substituents can interact with the phosphorus atom by direct resonance.This inverse relationship is due to a field effect of the substituent dipole which polarizes ?-electron clouds in the molecule.A corresponding shift in ?-electron density is likewise observed for 13C resonances of the two diastereotopic phenoxy groups, the phenylamino and phenyl moieties.Vicinal CH-NH coupling is shown to be dependent on the rate of NH proton exchange as influenced by resonance, temperature and solvent effects.
